2.02012-05-31 14:05:49 -06002015-09-13 12:56:14 -0600ECMDB04124M2MDB000624OxygenOxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131)DioxygenMolecular oxygenO2OxygenOxygen moleculeO231.998831.989829244dioxygensinglet oxygen7782-44-7O=OInChI=1S/O2/c1-2MYMOFIZGZYHOMD-UHFFFAOYSA-NLiquidCytosolExtra-organismPeriplasmmelting_point-218.4 oClogp-0.28ChemAxoniupacdioxygenChemAxonaverage_mass31.9988ChemAxonmono_mass31.989829244ChemAxonsmilesO=OChemAxonformulaO2ChemAxoninchiInChI=1S/O2/c1-2ChemAxoninchikeyMYMOFIZGZYHOMD-UHFFFAOYSA-NChemAxonpolar_surface_area34.14ChemAxonrefractivity2.89ChemAxonpolarizability1.53ChemAxonrotatable_bond_count0ChemAxonacceptor_count2ChemAxondonor_count0ChemAxonphysiological_charge0ChemAxonformal_charge0ChemAxonOxidative phosphorylationThe process of oxidative phosphorylation involves multiple interactions of ubiquinone with succinic acid, resulting in a fumaric acid and ubiquinol.
Ubiquinone interacts with succinic acid through a succinate:quinone oxidoreductase resulting in a fumaric acid an ubiquinol. This enzyme has various cofactors, ferroheme b, 2FE-2S, FAD, and 3Fe-4S iron-sulfur cluster.
Then 2 ubiquinol interact with oxygen and 4 hydrogen ion through a cytochrome bd-I terminal oxidase resulting in a 4 hydrogen ion transferred into the periplasmic space, 2 water returned into the cytoplasm and 2 ubiquinone, which stay in the inner membrane.
The ubiquinone interacts with succinic acid through a succinate:quinone oxidoreductase resulting in a fumaric acid an ubiquinol.
Then 2 ubiquinol interacts with oxygen and 4 hydrogen ion through a cytochrome bd-II terminal oxidase resulting in a 4 hydrogen ion transferred into the periplasmic space, 2 water returned into the cytoplasm and 2 ubiquinone, which stay in the inner membrane.
The ubiquinone interacts with succinic acid through a succinate:quinone oxidoreductase resulting in a fumaric acid an ubiquinol.
The 2 ubiquinol interact with oxygen and 8 hydrogen ion through a cytochrome bo terminal oxidase resulting in a 8 hydrogen ion transferred into the periplasmic space, 2 water returned into the cytoplasm and 2 ubiquinone, which stays in the inner membrane.
The ubiquinone then interacts with 5 hydrogen ion through a NADH dependent ubiquinone oxidoreductase I resulting in NAD, hydrogen ion released into the periplasmic space and an ubiquinol.
The ubiquinol is then processed reacting with oxygen, and 4 hydrogen through a ion cytochrome bd-I terminal oxidase resulting in 4 hydrogen ions released into the periplasmic space, 2 water molecules into the cytoplasm and 2 ubiquinones.
The ubiquinone then interacts with 5 hydrogen ion through a NADH dependent ubiquinone oxidoreductase I resulting in NAD, hydrogen ion released into the periplasmic space and an ubiquinol.
The 2 ubiquinol interact with oxygen and 8 hydrogen ion through a cytochrome bo terminal oxidase resulting in a 8 hydrogen ion transferred into the periplasmic space, 2 water returned into the cytoplasm and 2 ubiquinone, which stays in the inner membrane.
PW000919ec00190MetabolicAlanine, aspartate and glutamate metabolismec00250Nitrogen metabolism
The biological process of the nitrogen cycle is a complex interplay among many microorganisms catalyzing different reactions, where nitrogen is found in various oxidation states ranging from +5 in nitrate to -3 in ammonia.
The ability of fixing atmospheric nitrogen by the nitrogenase enzyme complex is present in restricted prokaryotes (diazotrophs). The other reduction pathways are assimilatory nitrate reduction and dissimilatory nitrate reduction both for conversion to ammonia, and denitrification. Denitrification is a respiration in which nitrate or nitrite is reduced as a terminal electron acceptor under low oxygen or anoxic conditions, producing gaseous nitrogen compounds (N2, NO and N2O) to the atmosphere.
Nitrate can be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK or a nitrate / nitrite transporter NarU. Nitrate is then reduced by a Nitrate Reductase resulting in the release of water, an acceptor and a Nitrite. Nitrite can also be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK
Nitrite can be reduced a NADPH dependent nitrite reductase resulting in water and NAD and Ammonia.
Nitrite can interact with hydrogen ion, ferrocytochrome c through a cytochrome c-552 ferricytochrome resulting in the release of ferricytochrome c, water and ammonia
Another process by which ammonia is produced is by a reversible reaction of hydroxylamine with a reduced acceptor through a hydroxylamine reductase resulting in an acceptor, water and ammonia.
Water and carbon dioxide react through a carbonate dehydratase resulting in carbamic acid. This compound reacts spontaneously with hydrogen ion resulting in the release of carbon dioxide and ammonia. Carbon dioxide can interact with water through a carbonic anhydrase resulting in hydrogen carbonate. This compound interacts with cyanate and hydrogen ion through a cyanate hydratase resulting in a carbamic acid.
Ammonia can be metabolized by reacting with L-glutamine and ATP driven glutamine synthetase resulting in ADP, phosphate and L-glutamine. The latter compound reacts with oxoglutaric acid and hydrogen ion through a NADPH dependent glutamate synthase resulting in the release of NADP and L-glutamic acid. L-glutamic acid reacts with water through a NADP-specific glutamate dehydrogenase resulting in the release of oxoglutaric acid, NADPH, hydrogen ion and ammonia.
PW000755ec00910MetabolicPyrimidine metabolismThe metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate.
Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate.
1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate.
3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate
4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate.
The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate.PW000942ec00240MetabolicTyrosine metabolismec00350Phenylalanine metabolismThe pathways of the metabolism of phenylalaline begins with the conversion of chorismate to prephenate through a P-protein (chorismate mutase:pheA). Prephenate then interacts with a hydrogen ion through the same previous enzyme resulting in a release of carbon dioxide, water and a phenolpyruvic acid. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosine.
Phenolpyruvic acid can also be obtained from a reversivle reaction with ammonia, a reduced acceptor and a D-amino acid dehydrogenase, resulting in a water, an acceptor and a D-phenylalanine, which can be then transported into the periplasmic space by aromatic amino acid exporter.
L-phenylalanine also interacts in two reversible reactions, one involved with oxygen through a catalase peroxidase resulting in a carbon dioxide and 2-phenylacetamide. The other reaction involved an interaction with oxygen through a phenylalanine aminotransferase resulting in a oxoglutaric acid and phenylpyruvic acid.
L-phenylalanine can be imported into the cytoplasm through an aromatic amino acid:H+ symporter AroP.
The compound can also be imported into the periplasmic space through a transporter: L-amino acid efflux transporter.PW000921ec00360MetabolicIsoquinoline alkaloid biosynthesisec00950Tropane, piperidine and pyridine alkaloid biosynthesisec00960Glycine, serine and threonine metabolismec00260Methane metabolismec00680Vitamin B6 metabolismec00750Sulfur metabolismThe sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion.
The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described.
The third variant of sulfur metabolism starts with the import of an alkyl sulfate into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. The alkyl sulfate is dehydrogenated and along with oxygen is converted to sulfite and an aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000922ec00920MetabolicTryptophan metabolismThe biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan.
The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoA
PW000815ec00380MetabolicPorphyrin and chlorophyll metabolismec00860Glyoxylate and dicarboxylate metabolismec00630Nicotinate and nicotinamide metabolismec00760beta-Alanine metabolismThe Beta-Alanine Metabolism starts with a product of Aspartate metabolism. Aspartate is decarboxylated by aspartate 1-decarboxylase, releasing carbon dioxide and Beta-alanine. Beta alanine is then metabolized through a pantothenate synthetase resulting in Pantothenic acid undergoes phosphorylation through a ATP driven pantothenate kinase, resulting in D-4-phosphopantothenate.
Pantothenate (vitamin B5) is the universal precursor for the synthesis of the 4'-phosphopantetheine moiety of coenzyme A and acyl carrier protein. Only plants and microorganismscan synthesize pantothenate de novo - animals require a dietary supplement. The enzymes of this pathway are therefore considered to be antimicrobial drug targets.PW000896ec00410MetabolicTaurine and hypotaurine metabolismec00430Riboflavin metabolismec00740Phenylpropanoid biosynthesisec00940Microbial metabolism in diverse environmentsec01120Two-component systemec02020Metabolic pathwayseco011002,3-dihydroxybenzoate biosynthesis2,3-dihydroxybenzoate is synthesized from chorismate via isochorismate and 2,3-dihydroxy-2,3-dihydrobenzoate. Chorismate is a key intermediate and branch point in the biosynthesis of many aromatic compounds.
The biosynthesis of 2,3-dihydroxybenzoate from chorismate is catalyzed by three enzymes EntC, EntB, and EntA. EntC catalyzes the conversion of chorismate to isochorismate. The N-terminal isochorismate lyase domain of EntB hydrolyzes the pyruvate group of isochorismate to produce 2,3-dihydro-2,3-dihydroxybenzoate. The conversion of this latter compound to 2,3-dihydroxybenzoate is catalyzed by the EntA dehydrogenase.
PW000751Metabolic2-Oxopent-4-enoate metabolismThe pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate.
The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate.
The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cyclePW001890MetabolicAspartate metabolismAspartate (seen in the center) is synthesized from and degraded to oxaloacetate , an intermediate of the TCA cycle, by a reversible transamination reaction with glutamate. As shown here, AspC is the principal transaminase that catalyzes this reaction, but TyrB also catalyzes it. Null mutations in aspC do not confer aspartate auxotrophy; null mutations in both aspC and tyrB do.
Aspartate is a constituent of proteins and participates in several other biosyntheses as shown here( NAD biosynthesis and Beta-Alanine Metabolism . Approximately 27 percent of the cell's nitrogen flows through aspartate
Aspartate can be synthesized from fumaric acid through a aspartate ammonia lyase. Aspartate also participates in the synthesis of L-asparagine through two different methods, either through aspartate ammonia ligase or asparagine synthetase B.
Aspartate is also a precursor of fumaric acid. Again it has two possible ways of synthesizing it. First set of reactions follows an adenylo succinate synthetase that yields adenylsuccinic acid and then adenylosuccinate lyase in turns leads to fumaric acid. The second way is through argininosuccinate synthase that yields argininosuccinic acid and then argininosuccinate lyase in turns leads to fumaric acid
PW000787MetabolicCollection of Reactions without pathwaysPW001891MetabolicNAD biosynthesisNicotinamide adenine dinucleotide (NAD) can be biosynthesized from L-aspartic acid.This amino acid reacts with oxygen through an L-aspartate oxidase resulting in a hydrogen ion, hydrogen peroxide and an iminoaspartic acid. The latter compound interacts with dihydroxyacetone phosphate through a quinolinate synthase A, resulting in a phosphate, water, and a quinolic acid. Quinolic acid interacts with phosphoribosyl pyrophosphate and hydrogen ion through a quinolinate phosphoribosyltransferase resulting in pyrophosphate, carbon dioxide and nicotinate beta-D-ribonucleotide. This last compound is adenylated through an ATP driven nicotinate-mononucleotide adenylyltransferase releasing a pyrophosphate and resulting in a nicotinic acid adenine dinucleotide.
Nicotinic acid adenine dinucleotide is processed through an NAD synthetase, NH3-dependent in two different manners.
In the first case, Nicotinic acid adenine dinucleotide interacts with ATP, L-glutamine and water through the enzyme and results in hydrogen ion, AMP, pyrophosphate, L-glutamic acid and NAD.
In the second case, Nicotinic acid adenine dinucleotide interacts with ATP and ammonium through the enzyme resulting in a pyrophosphate, AMP, hydrogen ion and NAD.
NAD then proceeds to regulate its own pathway by repressing L-aspartate oxidase.
As a general rule, most prokaryotes utilize the aspartate de novo pathway, in which the nicotinate moiety of NAD is synthesized from aspartate , while in eukaryotes, the de novo pathway starts with tryptophan.
PW000829MetabolicPorphyrin metabolismThe metabolism of porphyrin begins with with glutamic acid being processed by an ATP-driven glutamyl-tRNA synthetase by interacting with hydrogen ion and tRNA(Glu), resulting in amo, pyrophosphate and L-glutamyl-tRNA(Glu) Glutamic acid. Glutamic acid can be obtained as a result of L-glutamate metabolism pathway, glutamate / aspartate : H+ symporter GltP, glutamate:sodium symporter or a glutamate / aspartate ABC transporter .
L-glutamyl-tRNA(Glu) Glutamic acid interacts with a NADPH glutamyl-tRNA reductase resulting in a NADP, a tRNA(Glu) and a (S)-4-amino-5-oxopentanoate.
This compound interacts with a glutamate-1-semialdehyde aminotransferase resulting a 5-aminolevulinic acid. This compound interacts with a porphobilinogen synthase resulting in a hydrogen ion, water and porphobilinogen. The latter compound interacts with water resulting in hydroxymethylbilane synthase resulting in ammonium, and hydroxymethylbilane.
Hydroxymethylbilane can either be dehydrated to produce uroporphyrinogen I or interact with a uroporphyrinogen III synthase resulting in a water molecule and a uroporphyrinogen III.
Uroporphyrinogen I interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a coproporphyrinogen I
Uroporphyrinogen III can be metabolized into precorrin by interacting with a S-adenosylmethionine through a siroheme synthase resulting in hydrogen ion, an s-adenosylhomocysteine and a precorrin-1. On the other hand, Uroporphyrinogen III interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a Coproporphyrinogen III.
Precorrin-1 reacts with a S-adenosylmethionine through a siroheme synthase resulting in a S-adenosylhomocysteine and a Precorrin-2. The latter compound is processed by a NAD dependent uroporphyrin III C-methyltransferase [multifunctional] resulting in a NADH and a sirohydrochlorin. This compound then interacts with Fe 2+
uroporphyrin III C-methyltransferase [multifunctional] resulting in a hydrogen ion and a siroheme. The siroheme is then processed in sulfur metabolism pathway.
Uroporphyrinogen III can be processed in anaerobic or aerobic condition.
Anaerobic:
Uroporphyrinogen III interacts with an oxygen molecule, a hydrogen ion through a coproporphyrinogen III oxidase resulting in water, carbon dioxide and protoporphyrinogen IX. The latter compound then interacts with an 3 oxygen molecule through a protoporphyrinogen oxidase resulting in 3 hydrogen peroxide and a Protoporphyrin IX
Aerobic:
Uroporphyrinogen III reacts with S-adenosylmethionine through a coproporphyrinogen III dehydrogenase resulting in carbon dioxide, 5-deoxyadenosine, L-methionine and protoporphyrinogen IX. The latter compound interacts with a meanquinone through a protoporphyrinogen oxidase resulting in protoporphyrin IX.
The protoporphyrin IX interacts with Fe 2+ through a ferrochelatase resulting in a hydrogen ion and a ferroheme b. The ferroheme b can either be incorporated into the oxidative phosphorylation as a cofactor of the enzymes involved in that pathway or it can interact with hydrogen peroxide through a catalase HPII resulting in a heme D. Heme D can then be incorporated into the oxidative phosphyrlation pathway as a cofactor of the enzymes involved in that pathway. Ferroheme b can also interact with water and a farnesyl pyrophosphate through a heme O synthase resulting in a release of pyrophosphate and heme O. Heme O is then incorporated into the Oxidative phosphorylation pathway.
PW000936MetabolicSecondary Metabolites: Ubiquinol biosynthesisThe biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate.
The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol.
The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol.
The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8.
PW000981MetabolicTaurine Metabolism
Taurine is incorporated into the cytoplasm through a taurine ABC transporter. Once inside the cytoplasm, taurine interacts with an oxoglutaric acid and an oxygen through a taurine dioxygenase resulting in the release of succinic acid, sulfite , aminoacetaldehyde and carbon dioxidePW000774MetabolicTaurine Metabolism I Taurine is incorporated into the cytoplasm through a taurine ABC transporter. Once inside the cytoplasm, taurine interacts with an oxoglutaric acid and an oxygen through a taurine dioxygenase resulting in the release of succinic acid, sulfite , aminoacetaldehyde and carbon dioxidePW001028MetabolicVitamin B6 1430936196PW000891Metabolicarginine metabolismThe metabolism of L-arginine starts with the acetylation of L-glutamic acid resulting in a N-acetylglutamic acid while releasing a coenzyme A and a hydrogen ion. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NDPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine.
L-glutamine is used to synthesize carbamoyl phosphate through the interaction of L-glutamine, water, ATP, and hydrogen carbonate. This reaction yields ADP, L-glutamic acid, phosphate, and hydrogen ion.
Carbamoyl phosphate and ornithine are used to catalyze the production of citrulline through an ornithine carbamoyltransferase. Citrulline reacts with L-aspartic acid through an ATP dependent enzyme, argininosuccinate synthase to produce pyrophosphate, AMP and argininosuccinic acid. Argininosussinic acid is then lyase to produce L-arginine and fumaric acid.
L-arginine can be metabolized into succinic acid by two different sets of reactions:
1. Arginine reacts with succinyl-CoA through a arginine N-succinyltransferase resulting in N2-succinyl-L-arginine while releasing CoA and Hydrogen Ion. N2-succinyl-L-arginine is then dihydrolase to produce a N2-succinyl-L-ornithine through a N-succinylarginine dihydrolase. This compound in turn reacts with oxoglutaric acid through succinylornithine transaminase resulting in L-glutamic acid and N2-succinyl-L-glutamic acid 5-semialdehyde. This compoud in turn reacts with a NAD dependent dehydrogenase resulting in N2-succinylglutamate while releasing NADH and hydrogen ion. N2-succinylglutamate reacts with water through a succinylglutamate desuccinylase resulting in L-glutamic acid and
a succinic acid. The succinic acid is then incorporated in the TCA cycle
2.Argine reacts with carbon dioxide and a hydrogen ion through a biodegradative arginine decarboxylase, resulting in Agmatine. This compound is then transformed into putrescine by reacting with water and an agmatinase, and releasing urea. Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid.
Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle.
L-arginine is eventua lly metabolized into succinic acid which then goes to the TCA cyclePW000790Metabolicornithine metabolism
In the ornithine biosynthesis pathway of E. coli, L-glutamate is acetylated to N-acetylglutamate by the enzyme N-acetylglutamate synthase, encoded by the argA gene. The acetyl donor for this reaction is acetyl-CoA. N-acetylglutamic acid is then phosphorylated via an ATP driven acetylglutamate kinase which yields a N-acetyl-L-glutamyl 5-phosphate. This compound undergoes a NADPH dependent reduction resulting in N-acetyl-L-glutamate 5-semialdehyde. This compound reacts with L-glutamic acid through a acetylornithine aminotransferase / N-succinyldiaminopimelate aminotransferase to produce a N-acetylornithine which is then deacetylated through a acetylornithine deacetylase which yield an ornithine. Ornithine interacts with hydrogen ion through a Ornithine decarboxylase resulting in a carbon dioxide release and a putrescine
Putrescine can be metabolized by reaction with either l-glutamic acid or oxoglutaric acid. If putrescine reacts with L-glutamic acid, it reacts through an ATP mediated gamma-glutamylputrescine producing a hydrogen ion, ADP, phosphate and gamma-glutamyl-L-putrescine. This compound is reduced by interacting with oxygen, water and a gamma-glutamylputrescine oxidoreductase resulting in ammonium, hydrogen peroxide and 4-gamma-glutamylamino butanal. This compound is dehydrogenated through a NADP mediated reaction lead by gamma-glutamyl-gamma-aminobutaryaldehyde dehydrogenase resulting in hydrogen ion, NADPH and 4-glutamylamino butanoate. In turn, the latter compound reacts with water through a gamma-glutamyl-gamma-aminobutyrate hydrolase resulting in L-glutamic acid and Gamma aminobutyric acid. On the other hand, if putrescine reacts with oxoglutaric acid through a putrescine aminotransferase, it results in L-glutamic acid, and a 4-aminobutyraldehyde. This compound reacts with water through a NAD dependent gamma aminobutyraldehyde dehydrogenase resulting in hydrogen ion, NADH and gamma-aminobutyric acid.
Gamma Aaminobutyric acid reacts with oxoglutaric acid through 4-aminobutyrate aminotransferase resulting in L-glutamic acid and succinic acid semialdehyde. This compound in turn can react with with either NADP or NAD to result in the production of succinic acid through succinate-semialdehyde dehydrogenase or aldehyde dehydrogenase-like protein yneI respectively. Succinic acid can then be integrated in the TCA cycle.
PW000791Metabolicsulfur metabolism (butanesulfonate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case 1-butanesulfonate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. 1-butanesulfonate is dehydrogenated and along with oxygen is converted to sulfite and betaine aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000923Metabolicsulfur metabolism (ethanesulfonate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case ethanesulfonate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. Ethanesulfonate is dehydrogenated and along with oxygen is converted to sulfite and betaine aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000925Metabolicsulfur metabolism (isethionate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case isethionate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. Isethionate is dehydrogenated and along with oxygen is converted to sulfite and betaine aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000926Metabolicsulfur metabolism (methanesulfonate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case methanesulfonate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. Methanesulfonate is dehydrogenated and along with oxygen is converted to sulfite and an aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000927Metabolicsulfur metabolism (propanesulfonate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case 3-(N-morpholino)propanesulfonate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. 3-(N-morpholino)propanesulfonate is dehydrogenated and along with oxygen is converted to sulfite and betaine aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000924MetabolicPhenylethylamine metabolismThe process of phenylethylamine metabolism starts with 2-phenylethylamine interacting with an oxygen molecule and a water molecule in the periplasmic space through a phenylethylamine oxidase. This reaction results in the release of a hydrogen peroxide, ammonium and phenylacetaldehyde.
Phenylacetaldehyde is introduced into the cytosol and degraded into phenylacetate by reaction with a phenylacetaldehyde dehydrogenase. This reaction involves phenylacetaldehyde interacting with NAD, and a water molecule and then resulting in the release of NADH, and 2 hydrogen ion.
Phenylacetate is then degraded. The first step involves phenylacetate interacting with an coenzyme A and an ATP driven phenylacetate-CoA ligase resulting in the release of a AMP, a diphosphate and a phenylacetyl-CoA. This resulting compound the interacts with a hydrogen ion, NADPH, and oxygen molecule through a ring 1,2-phenylacetyl-CoA epoxidase protein complex resulting in the release of a water molecule, an NADP and a 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA. This compound is then metabolized by a ring 1,2 epoxyphenylacetyl-CoA isomerase resulting in a 2-oxepin-2(3H)-ylideneacetyl-CoA. This compound is then hydrolated through a oxepin-CoA hydrolase resulting in a 3-oxo-5,6-didehydrosuberyl-CoA semialdehyde. This commpound then interacts with a water molecule and NADP driven 3-oxo-5,6-dehydrosuberyl-CoA semialadehyde dehydrogenase resulting in 2 hydrogen ions, a NADPH and a 3-oxo-5,6-didehydrosuberyl-CoA. The resulting compound interacts with a coenzyme A and a 3-oxo-5,6 dehydrosuberyl-CoA thiolase resulting in an acetyl-CoA and a 2,3-didehydroadipyl-CoA. This resulting compound is the hydrated by a 2,3-dehydroadipyl-CoA hydratas resulting in a 3-hydroxyadipyl-CoA whuch is dehydrogenated through an NAD driven 3-hydroxyadipyl-CoA dehydrogenase resulting in a NADH, a hydrogen ion and a 3-oxoadipyl-CoA. The latter compound then interacts with conezyme A through a beta-ketoadipyl-CoA thiolase resulting in an acetyl-CoA and a succinyl-CoA. The succinyl-CoA is then integrated into the TCA cycle.PW002027MetabolicUracil degradation IIIPW002026Metabolic2-Oxopent-4-enoate metabolism 2The pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate. The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate. The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cyclePW002035MetabolicPutrescine Degradation IISeveral metabolic pathways for putrescine degradation as a source of nitrogen for E. coli K-12 are known. The first putrescine degradation pathway was found in in 1985. That pathway is dedicated to the degradation of intracellular putrescine. A second pathway was found in E. coli K-12 twenty years later. This pathway seems to be dedicated to the degradation of extracellular putrescine.
The pathway was discovered following the discovery of a cluster of seven unassigned genes on the E. coli K-12 chromosome. In addition to a putrescine transporter, encoded by the puuP gene, the cluster contains four genes that encode the enzymes involved in this pathway, and two additional genes (puuE and puuR) that encode an enzyme involved in the catabolism of GABA (see superpathway of 4-aminobutanoate degradation) and a regulator.
In this pathway, putrescine is γ-glutamylated at the expense of an ATP molecule. The resulting γ-glutamyl-putrescine is oxidized to γ-glutamyl-γ-aminobutyraldehyde, which is then dehydrogenated into 4-(glutamylamino) butanoate. In the last step, the γ-glutamyl group is removed by hydrolysis, generating 4-aminobutyrate.
The key difference between this pathway and putrescine degradation I is the γ-glutamylation of putrescine. In the other pathway, putrescine is degraded directly to 4-amino-butanal.
Wild type E. coli cells are unable to utilize putrescine as the sole source of carbon at temperatures above 30°C. It is possible to select for mutants that possess this ability; these mutants contain elevated levels of the enzymes in this pathway. (EcoCyc)PW002054MetabolicSecondary Metabolites: Ubiquinol biosynthesis 2The biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate. The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol. The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol. The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8.PW002036MetabolicSuperoxide Radicals DegradationGram-negative bacteria commonly synthesize both cytoplasmic and periplasmic isozymes of SOD as their frontline defense against superoxide anion (O2-). E. coli contains two cytoplasmic SOD isozymes, one each of the manganese- and iron-cofactored types (MnSOD and FeSOD), and secretes a copper, zinc-cofactored enzyme (CuZnSOD) to the periplasm. Periplasmic superoxide may be generated by autooxidation of dihydromenaquinone in the cytoplasmic membrane.
In E. coli, the MnSOD and FeSOD enzymes (encoded by sodA and sodB, respectively) are structurally and kinetically similar. Unlike MnSOD and FeSOD, CuZnSOD is monomeric. Regulation of the three enzymes is complex. Under anaerobic conditions, FeSOD is the only superoxide dismutase enzyme present in E. coli. MnSOD is induced by aerobic growth and a variety of environmental stress conditions. CuZnSOD constitutes only a small fraction of superoxide dismutase activity in the cell; its expression is induced in stationary phase.
In E. coli, with rising H2O2 concentration, catalase is strongly induced and becomes the primary scavenging enzyme. E. coli expresses two catalases, known as HPI and HPII, that are encoded by katG and katE, respectively. While katG katE mutants could not degrade millimolar concentrations of H2O2, they were subsequently found to retain the ability to degrade H2O2 when it was present at low micromolar concentrations. This residual activity is due to an enzyme known as alkylhydroperoxide reductase (Ahp). This two-component enzyme had originally been identified as a scavenger of organic hydroperoxides.
SOD mutants of E. coli are unable to perform normal sulfur metabolism. Both SOD and catalase/peroxidase mutants of E. coli are incapable of synthesizing aromatic products, including amino acids.
SoxRS regulon is turned on by any condition that increases superoxide radical production in E. coli. One of its products is Mn-SOD. Another independent regulon turned on in response to H2O2 is referred to as the OxyR regulon. (EcoCyc)PW002053MetabolicL-threonine degradation to methylglyoxalL-threonine is degrade into methylglyoxal (pyruvaldehyde) by first reacting with a NDA dependent threonine dehydrogenase resulting in the release of a hydrogen ion, an NADH and a 2-amino-3-oxobutanoate. The latter compound reacts spontaneously with a hydrogen ion resulting in the release of a carbon dioxide and a aminoacetone. The aminoacetone in turn reacts with an oxygen and a water molecule through an aminoacetone oxidase resulting in the release of a hydrogen peroxide, ammonium and a methylglyoxal which can then be incorporated in the methylglyoxal degradation pathways.PW002106Metabolicpyruvate to cytochrome bd terminal oxidase electron transferThe reaction of pyruvate to cytochrome bd terminal oxidase electron transfer starts with 2 pyruvate and 2 water molecules reacting in a pyruvate oxidase resulting in the release of 4 electrons into the inner membrane, and releasing 2 carbon dioxide molecules , 2 acetate and 4 hydrogen ion into the cytosol.
2 ubiquinone,4 hydrogen ion and 4 electron ion react resulting in the release of 2 ubiquinol . The 2 ubiquinol in turn release 4 hydrogen ions into the periplasmic space through a cytochrome bd-I terminal oxidase and releasing 4 electrons through the enzyme. Oxygen and 4 hydrogen ion reacts with the 4 electrons resulting in 2 water molecules.PW002087Metabolicphenylacetate degradation I (aerobic)PWY0-321NAD biosynthesis I (from aspartate)PYRIDNUCSYN-PWYuracil degradation IIIPWY0-1471threonine degradation III (to methylglyoxal)THRDLCTCAT-PWYphenylethylamine degradation I2PHENDEG-PWYpyridoxal 5'-phosphate salvage pathwayPLPSAL-PWYpyridoxal 5'-phosphate biosynthesis IPYRIDOXSYN-PWYputrescine degradation IIPWY0-1221cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoatePWY-6690ubiquinol-8 biosynthesis (prokaryotic)PWY-6708two-component alkanesulfonate monooxygenaseALKANEMONOX-PWYtaurine degradation IVPWY0-981heme biosynthesis from uroporphyrinogen-III IHEME-BIOSYNTHESIS-IIsuperpathway of heme biosynthesis from uroporphyrinogen-IIIPWY0-14153-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoateHCAMHPDEG-PWYNADH to cytochrome <i>bd</i> oxidase electron transferPWY0-1334succinate to cytochrome <i>bd</i> oxidase electron transferPWY0-1353succinate to cytochrome <i>bo</i> oxidase electron transferPWY0-1329NADH to cytochrome <i>bo</i> oxidase electron transferPWY0-1335superoxide radicals degradationDETOX1-PWYSpecdb::CMs2742Specdb::CMs133063Specdb::CMs140797Specdb::MsMs27272Specdb::MsMs27273Specdb::MsMs27274Specdb::MsMs33830Specdb::MsMs33831Specdb::MsMs33832Specdb::MsMs2324095Specdb::MsMs2324096Specdb::MsMs2324097HMDB01377977952C0000715379OXYGEN-MOLECULEOXYOxygenKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Terashvili, M., Pratt, P. F., Gebremedhin, D., Narayanan, J., Harder, D. R. (2006). "Reactive oxygen species cerebral autoregulation in health and disease." 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(2007), 26pp.http://hmdb.ca/system/metabolites/msds/000/001/239/original/HMDB01377.pdf?1358460279Superoxide dismutase [Mn]P00448SODM_ECOLIsodAhttp://ecmdb.ca/proteins/P00448.xmlAromatic-amino-acid aminotransferaseP04693TYRB_ECOLItyrBhttp://ecmdb.ca/proteins/P04693.xml3-phenylpropionate/cinnamic acid dioxygenase subunit alphaP0ABR5HCAE_ECOLIhcaEhttp://ecmdb.ca/proteins/P0ABR5.xml2,3-dihydroxyphenylpropionate/2,3-dihydroxicinnamic acid 1,2-dioxygenaseP0ABR9MHPB_ECOLImhpBhttp://ecmdb.ca/proteins/P0ABR9.xml3-phenylpropionate/cinnamic acid dioxygenase ferredoxin subunitP0ABW0HCAC_ECOLIhcaChttp://ecmdb.ca/proteins/P0ABW0.xmlProtoporphyrinogen oxidaseP0ACB4HEMG_ECOLIhemGhttp://ecmdb.ca/proteins/P0ACB4.xmlProbable quinol monooxygenase ygiNP0ADU2YGIN_ECOLIygiNhttp://ecmdb.ca/proteins/P0ADU2.xmlGlycolate oxidase subunit glcDP0AEP9GLCD_ECOLIglcDhttp://ecmdb.ca/proteins/P0AEP9.xmlSuperoxide dismutase [Cu-Zn]P0AGD1SODC_ECOLIsodChttp://ecmdb.ca/proteins/P0AGD1.xmlSuperoxide dismutase [Fe]P0AGD3SODF_ECOLIsodBhttp://ecmdb.ca/proteins/P0AGD3.xmlL-aspartate oxidaseP10902NADB_ECOLInadBhttp://ecmdb.ca/proteins/P10902.xmlCatalase-peroxidaseP13029KATG_ECOLIkatGhttp://ecmdb.ca/proteins/P13029.xmlCatalase HPIIP21179CATE_ECOLIkatEhttp://ecmdb.ca/proteins/P21179.xmlFlavohemoproteinP24232HMP_ECOLIhmphttp://ecmdb.ca/proteins/P24232.xmlAdenine deaminaseP31441ADEC_ECOLIadehttp://ecmdb.ca/proteins/P31441.xmlMalate:quinone oxidoreductaseP33940MQO_ECOLImqohttp://ecmdb.ca/proteins/P33940.xmlCoproporphyrinogen-III oxidase, aerobicP36553HEM6_ECOLIhemFhttp://ecmdb.ca/proteins/P36553.xmlBlue copper oxidase cueOP36649CUEO_ECOLIcueOhttp://ecmdb.ca/proteins/P36649.xmlAlpha-ketoglutarate-dependent taurine dioxygenaseP37610TAUD_ECOLItauDhttp://ecmdb.ca/proteins/P37610.xmlGamma-glutamylputrescine oxidoreductaseP37906PUUB_ECOLIpuuBhttp://ecmdb.ca/proteins/P37906.xmlPrimary amine oxidaseP46883AMO_ECOLItynAhttp://ecmdb.ca/proteins/P46883.xmlGlycolate oxidase iron-sulfur subunitP52074GLCF_ECOLIglcFhttp://ecmdb.ca/proteins/P52074.xml2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol hydroxylaseP75728UBIF_ECOLIubiFhttp://ecmdb.ca/proteins/P75728.xmlProbable phenylacetic acid degradation NADH oxidoreductase paaEP76081PAAE_ECOLIpaaEhttp://ecmdb.ca/proteins/P76081.xml3-phenylpropionate/cinnamic acid dioxygenase ferredoxin--NAD(+) reductase componentP77650HCAD_ECOLIhcaDhttp://ecmdb.ca/proteins/P77650.xmlFMN reductaseP80644SSUE_ECOLIssuEhttp://ecmdb.ca/proteins/P80644.xmlAlkanesulfonate monooxygenaseP80645SSUD_ECOLIssuDhttp://ecmdb.ca/proteins/P80645.xml3-phenylpropionate/cinnamic acid dioxygenase subunit betaQ47140HCAF_ECOLIhcaFhttp://ecmdb.ca/proteins/Q47140.xmlUbiquinol oxidase subunit 2P0ABJ1CYOA_ECOLIcyoAhttp://ecmdb.ca/proteins/P0ABJ1.xmlPutative flavin reductase rutFP75893RUTF_ECOLIrutFhttp://ecmdb.ca/proteins/P75893.xmlPhenylacetic acid degradation protein paaBP76078PAAB_ECOLIpaaBhttp://ecmdb.ca/proteins/P76078.xmlGlycolate oxidase subunit glcEP52073GLCE_ECOLIglcEhttp://ecmdb.ca/proteins/P52073.xmlCytochrome o ubiquinol oxidase protein cyoDP0ABJ6CYOD_ECOLIcyoDhttp://ecmdb.ca/proteins/P0ABJ6.xmlPutative monooxygenase rutAP75898RUTA_ECOLIrutAhttp://ecmdb.ca/proteins/P75898.xmlPhenylacetic acid degradation protein paaAP76077PAAA_ECOLIpaaAhttp://ecmdb.ca/proteins/P76077.xmlCytochrome bd-II oxidase subunit 2P26458APPB_ECOLIappBhttp://ecmdb.ca/proteins/P26458.xml2-octaprenyl-6-methoxyphenol hydroxylaseP25534UBIH_ECOLIubiHhttp://ecmdb.ca/proteins/P25534.xmlProbable ubiquinone biosynthesis protein ubiBP0A6A0UBIB_ECOLIubiBhttp://ecmdb.ca/proteins/P0A6A0.xmlCytochrome bd-II oxidase subunit 1P26459APPC_ECOLIappChttp://ecmdb.ca/proteins/P26459.xmlN-methyl-L-tryptophan oxidaseP40874MTOX_ECOLIsolAhttp://ecmdb.ca/proteins/P40874.xmlPhenylacetic acid degradation protein paaDP76080PAAD_ECOLIpaaDhttp://ecmdb.ca/proteins/P76080.xmlCytochrome d ubiquinol oxidase subunit 2P0ABK2CYDB_ECOLIcydBhttp://ecmdb.ca/proteins/P0ABK2.xmlUbiquinol oxidase subunit 1P0ABI8CYOB_ECOLIcyoBhttp://ecmdb.ca/proteins/P0ABI8.xml3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylaseP77397MHPA_ECOLImhpAhttp://ecmdb.ca/proteins/P77397.xmlPhenylacetic acid degradation protein paaCP76079PAAC_ECOLIpaaChttp://ecmdb.ca/proteins/P76079.xmlCytochrome d ubiquinol oxidase subunit 1P0ABJ9CYDA_ECOLIcydAhttp://ecmdb.ca/proteins/P0ABJ9.xmlPyridoxine/pyridoxamine 5'-phosphate oxidaseP0AFI7PDXH_ECOLIpdxHhttp://ecmdb.ca/proteins/P0AFI7.xmlCytochrome o ubiquinol oxidase subunit 3P0ABJ3CYOC_ECOLIcyoChttp://ecmdb.ca/proteins/P0ABJ3.xmlferritin iron storage protein (cytoplasmic)P0A998ftnAhttp://ecmdb.ca/proteins/P0A998.xmlpredicted 2Fe-2S cluster-containing proteinP0ABR7yeaWhttp://ecmdb.ca/proteins/P0ABR7.xmlAlpha-ketoglutarate-dependent dioxygenase AlkBP05050alkBhttp://ecmdb.ca/proteins/P05050.xmlBacterioferritinP0ABD3BFR_ECOLIbfrhttp://ecmdb.ca/proteins/P0ABD3.xmlCytochrome bd-I ubiquinol oxidase subunit XP56100CYDX_ECOLIcydXhttp://ecmdb.ca/proteins/P56100.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xml2 Hydrogen ion + Oxygen + Ubiquinol-8 > Water + Ubiquinone-8 +2 Hydrogen ion4 Hydrogen ion + Oxygen + Ubiquinol-8 > Water + Ubiquinone-8 +4 Hydrogen ion2 Hydrogen ion + Menaquinol 8 + Oxygen > Water + Menaquinone 8 +2 Hydrogen ionHydrogen ion + NADH + Oxygen + Uracil > NAD + Ureidoacrylate peracidHydrogen ion + NADPH + Oxygen + Phenylacetyl-CoA > Water + NADP + Ring 1,2-epoxyphenylacetyl-CoA2 Hydrogen peroxide <>2 Water + OxygenR00009CATAL-RXNtrans-Cinnamic acid + Hydrogen ion + NADH + Oxygen > cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NADR06783RXN-12072Hydrogen ion + NADH + Oxygen + Hydrocinnamic acid > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD2 Hydrogen ion + 2 Superoxide anion > Hydrogen peroxide + OxygenSUPEROX-DISMUT-RXN4 Copper + 4 Hydrogen ion + Oxygen >4 Copper +2 Water4 Iron + 4 Hydrogen ion + Oxygen >4 Fe3+ +2 Water3-(3-Hydroxyphenyl)propanoic acid + Hydrogen ion + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NADR067863-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NADR06787RXN-100403-(2,3-Dihydroxyphenyl)propionic acid + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononadienedicarboxylateR043761.13.11.16-RXNTrans-2,3-Dihydroxycinnamate + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioateR06788RXN-12073alpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acidR053202-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + Oxygen > 2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinolFMNH + Oxygen + Sulfoacetate > Flavin Mononucleotide + Glyoxylic acid + Hydrogen ion + Water + SulfiteFMNH + Isethionic acid + Oxygen > Flavin Mononucleotide + Glycolaldehyde + Hydrogen ion + Water + SulfiteRXN-13418FMNH + Methanesulfonate + Oxygen > Formaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + SulfiteButanesulfonate + FMNH + Oxygen > Butanal + Flavin Mononucleotide + Hydrogen ion + Water + SulfiteRXN0-6973Ethanesulfonate + FMNH + Oxygen > Acetaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + SulfiteWater + Oxygen + Sarcosine > Formaldehyde + Glycine + Hydrogen peroxideN-Methyltryptophan + Water + Oxygen > Formaldehyde + Hydrogen peroxide + L-TryptophanRXN0-301gamma-Glutamyl-L-putrescine + Water + Oxygen > gamma-Glutamyl-gamma-butyraldehyde + Hydrogen peroxide + AmmoniumRXN0-3921Dopamine + Water + Oxygen > 3,4-Dihydroxyphenylacetaldehyde + Hydrogen peroxide + AmmoniumWater + Oxygen + Tyramine > 4-Hydroxyphenylacetaldehyde + Hydrogen peroxide + AmmoniumWater + Oxygen + Phenylethylamine > Hydrogen peroxide + Ammonium + PhenylacetaldehydeWater + Oxygen + Pyridoxamine 5'-phosphate > Hydrogen peroxide + Ammonium + Pyridoxal 5'-phosphateOxygen + Pyridoxine 5'-phosphate > Hydrogen peroxide + Pyridoxal 5'-phosphateR00278PNPOXI-RXNCoproporphyrin III + 2 Hydrogen ion + Oxygen <>2 Carbon dioxide +2 Water + Protoporphyrinogen IXR03220NADH + 2 Nitric oxide + 2 Oxygen > Hydrogen ion + NAD +2 NitrateNADPH + 2 Nitric oxide + 2 Oxygen > Hydrogen ion + NADP +2 NitrateL-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acidR00481L-ASPARTATE-OXID-RXN2-Octaprenyl-6-methoxyphenol + Oxygen > 2-Octaprenyl-6-methoxy-1,4-benzoquinolMenaquinol 8 + 2 Oxygen >2 Hydrogen ion + Menaquinone 8 +2 Superoxide anion2 Oxygen + Ubiquinol-8 >2 Hydrogen ion +2 Superoxide anion + Ubiquinone-82-Octaprenylphenol + Oxygen > 2-Octaprenyl-6-hydroxyphenolOxygen + Protoporphyrinogen IX >3 Water + Protoporphyrin IXOxygen + 4 Fe2+ + 4 Hydrogen ion + 4 Fe2+ <>4 Fe3+ +2 WaterR00078Pyridoxamine 5'-phosphate + Water + Oxygen <> Pyridoxal 5'-phosphate + Ammonia + Hydrogen peroxideR00277PMPOXI-RXNPyridoxine 5'-phosphate + Oxygen <> Hydrogen peroxide + Pyridoxal 5'-phosphateR00278L-Aspartic acid + Water + Oxygen <> Oxalacetic acid + Ammonia + Hydrogen peroxideR00357Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxideR00475L-Aspartic acid + Oxygen <> Iminoaspartic acid + Hydrogen peroxideR00481L-ASPARTATE-OXID-RXNL-Phenylalanine + Oxygen <> 2-Phenylacetamide + Carbon dioxideR00698Pyridoxamine + Water + Oxygen <> Pyridoxal + Ammonia + Hydrogen peroxideR01710Pyridoxine + Oxygen <> Pyridoxal + Hydrogen peroxideR01711Tyramine + Water + Oxygen <> 4-Hydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxideR02382Aminoacetone + Water + Oxygen <> Pyruvaldehyde + Ammonia + Hydrogen peroxideR02529Phenylethylamine + Oxygen + Water <> Phenylacetaldehyde + Ammonia + Hydrogen peroxideR026132 3-Hydroxyanthranilic acid + 4 Oxygen <> Cinnavalininate +2 Superoxide anion +2 Hydrogen peroxide +2 Hydrogen ionR026701,3-Diaminopropane + Oxygen + Water <> 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxideR03139Coproporphyrin III + Oxygen <> Protoporphyrinogen IX +2 Carbon dioxide +2 WaterR03220N-Methylputrescine + Oxygen + Hydrogen ion <> 1-Methylpyrrolinium + Hydrogen peroxide + AmmoniaR04027Dopamine + Water + Oxygen <> 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxideR043003-(2,3-Dihydroxyphenyl)propionic acid + Oxygen <> 2-Hydroxy-6-ketononadienedicarboxylateR043762-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <> 2-Octaprenyl-6-hydroxyphenol + NADP + WaterR049872-Octaprenyl-6-methoxyphenol + Oxygen + NADPH <> 2-octaprenyl-6-methoxy-1,4-benzoquinone + NADP + WaterR049894-Chlorobiphenyl + Oxygen + NADH + Hydrogen ion <> cis-2,3-Dihydro-2,3-dihydroxy-4'-chlorobiphenyl + NADR052614-Chlorobiphenyl + Oxygen + NADPH + Hydrogen ion <> cis-2,3-Dihydro-2,3-dihydroxy-4'-chlorobiphenyl + NADPR05262Biphenyl + Oxygen + NADH + Hydrogen ion <> cis-2,3-Dihydro-2,3-dihydroxybiphenyl + NADR05263Biphenyl + Oxygen + NADPH + Hydrogen ion <> cis-2,3-Dihydro-2,3-dihydroxybiphenyl + NADPR052644-Nitrocatechol + Oxygen + 3 Hydrogen ion <> Benzene-1,2,4-triol + Nitrite + WaterR05265Taurine + alpha-Ketoglutarate + Oxygen <> Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxideR05320Ethylbenzene + Oxygen + NADH + Hydrogen ion <> cis-1,2-Dihydro-3-ethylcatechol + NADR054402-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone + Oxygen + NADPH + Hydrogen ion <> 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + NADP + WaterR06146Methylamine + Oxygen + Water <> Formaldehyde + Ammonia + Hydrogen peroxideR06154alpha-Pinene + Reduced acceptor + Oxygen <> Myrtenol + Water + AcceptorR06401alpha-Pinene + Oxygen + 2 Hydrogen ion + 2 e- <> Pinocarveol + WaterR06404Cadaverine + Water + Oxygen <> 5-Aminopentanal + Ammonia + Hydrogen peroxideR06740Hydrocinnamic acid + Oxygen + NADH + Hydrogen ion <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NADR06782HCAMULTI-RXNtrans-Cinnamic acid + Oxygen + NADH + Hydrogen ion <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NADR067833-(3-Hydroxyphenyl)propanoic acid + Oxygen + NADH + Hydrogen ion <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NADR067863-Hydroxycinnamic acid + Oxygen + NADH + Hydrogen ion <> Trans-2,3-Dihydroxycinnamate + Water + NADR06787Trans-2,3-Dihydroxycinnamate + Oxygen <> 2-Hydroxy-6-ketononatrienedioateR06788Bisphenol A + NADH + Hydrogen ion + Oxygen <> 1,2-Bis(4-hydroxyphenyl)-2-propanol + NAD + WaterR068832,2-Bis(4-hydroxyphenyl)-1-propanol + NADH + Hydrogen ion + Oxygen <> 2,3-Bis(4-hydroxyphenyl)-1,2-propanediol + NAD + WaterR06888gamma-Glutamyl-L-putrescine + Water + Oxygen <> gamma-Glutamyl-gamma-butyraldehyde + Ammonia + Hydrogen peroxideR07415Anthracene + Oxygen + 2 Hydrogen ion + 2 e- <> Anthracene-9,10-dihydrodiolR07687Phenylboronic acid + Oxygen <> Phenol + Boric acidR07697Aniline + Oxygen <> Pyrocatechol + AmmoniaR07700Nitrobenzene + Oxygen <> Pyrocatechol + NitriteR077062-Polyprenylphenol + Oxygen + NADPH <> 2-Polyprenyl-6-hydroxyphenol + NADP + WaterR087682-Polyprenyl-6-methoxyphenol + Oxygen <> 2-Polyprenyl-6-methoxy-1,4-benzoquinone + WaterR087732-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinone + Oxygen + NADPH + Hydrogen ion <> 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + NADP + WaterR08775Phenylacetyl-CoA + Oxygen + NADPH + Hydrogen ion <> 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoAR09838Uracil + FMNH + Oxygen <> Ureidoacrylate peracid + Flavin MononucleotideR09936RXN0-64442-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion > 2-Octaprenyl-6-hydroxyphenol + Water + NADPR049872-OCTAPRENYLPHENOL-HYDROX-RXNOxygen + Iron > Superoxide anion + Fe<SUP>3+</SUP>RXN-125412-Pyrocatechuic acid + Oxygen > Hydrogen ion + 2-CarboxymuconateRXN0-2943NAD(P)H + Cr<sup>6+</sup> + Oxygen > NAD(P)<sup>+</sup> + Cr<sup>3+</sup> + Hydrogen peroxideRXN0-3381menadiol + Oxygen > Hydrogen ion + menadione + Superoxide anionRXN0-34412-Octaprenyl-6-methoxyphenol + Oxygen + NADPH + Hydrogen ion > 2-Octaprenyl-6-methoxy-1,4-benzoquinol + Water + NADP2-OCTAPRENYL-6-METHOXYPHENOL-HYDROX-RXNAminoacetone + Water + Oxygen > Hydrogen ion + Pyruvaldehyde + Ammonia + Hydrogen peroxideR02529AMACETOXID-RXNan aliphatic amine + Water + Oxygen > an aldehyde + Ammonia + Hydrogen peroxide + Hydrogen ionAMINEOXID-RXNWater + Oxygen + Phenylethylamine > Hydrogen ion + Hydrogen peroxide + Ammonia + PhenylacetaldehydeR02613AMINEPHEN-RXNHydrogen peroxide > Water + OxygenCATAL-RXNHydrocinnamic acid + NADH + Oxygen + Hydrogen ion > cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NADHCAMULTI-RXNOxygen + L-Aspartic acid > Hydrogen ion + Hydrogen peroxide + Iminoaspartic acidL-ASPARTATE-OXID-RXNL-Malic acid + Oxygen <> Oxalacetic acid + Hydrogen peroxideMALOX-RXNHydrogen ion + 3-(3-Hydroxyphenyl)propionate + NADH + Oxygen > Water + 3-(2,3-Dihydroxyphenyl)propionic acid + NADMHPHYDROXY-RXN2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + Oxygen + a reduced electron acceptor > 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + Water + an oxidized electron acceptorOCTAPRENYL-METHYL-METHOXY-BENZOQ-OH-RXNOxygen + Water + Pyridoxamine 5'-phosphate > Hydrogen ion + Hydrogen peroxide + Ammonia + Pyridoxal 5'-phosphatePMPOXI-RXNProtoporphyrinogen IX + Oxygen > Protoporphyrin IX + Hydrogen peroxidePROTOPORGENOXI-RXNquercetin + Oxygen > 2-protocatechuoylphloroglucinolcarboxylate + carbon monoxideQUERCETIN-23-DIOXYGENASE-RXNNAD(P)H + Nitric oxide + Oxygen > NAD(P)<sup>+</sup> + Nitrate + Hydrogen ionR621-RXNHydrogen peroxide > Water + OxygenRXN-12121a ubiquinol + Oxygen > a ubiquinone + WaterRXN0-5266a methylated nucleobase within DNA + Oxygen + Oxoglutaric acid Hydrogen ion + a nucleobase within DNA + Carbon dioxide + Formaldehyde + Succinic acidRXN-12353Thymine + Oxygen + FMNH > (<i>Z</i>)-2-methylureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ionRXN-12886a primary amine + Water + Oxygen > an aldehyde + Ammonia + Hydrogen peroxideRXN-9597Coproporphyrinogen III + Oxygen + Hydrogen ion > Protoporphyrinogen IX + Carbon dioxide + WaterRXN0-1461Iron + Hydrogen ion + Oxygen > Fe<SUP>3+</SUP> + WaterRXN0-1483Phenylacetyl-CoA + Oxygen + NADPH + Hydrogen ion > 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + WaterRXN0-2042an alkanesulfonate + Oxygen + FMNH > an aldehyde + Sulfite + Water + Flavin Mononucleotide + Hydrogen ionRXN0-280Cu<SUP>+</SUP> + Hydrogen ion + Oxygen > Copper + WaterRXN0-2945Taurine + Oxoglutaric acid + Oxygen > Hydrogen ion + Aminoacetaldehyde + Sulfite + Succinic acid + Carbon dioxideRXN0-299Oxygen + Hydrogen ion + a ubiquinol > a ubiquinone + Water + Hydrogen ionRXN0-5266L-2-Hydroxyglutaric acid + Oxygen > Oxoglutaric acid + Hydrogen peroxideRXN0-5364Uracil + Oxygen + FMNH > Hydrogen ion + Ureidoacrylate peracid + Flavin MononucleotideRXN0-6444Butanesulfonate + Oxygen + FMNH > Butanal + Sulfite + Water + Flavin Mononucleotide + Hydrogen ionRXN0-6973N1-Methyladenine + Oxygen + Oxoglutaric acid > Hydrogen ion + Adenine + Carbon dioxide + Formaldehyde + Succinic acidRXN0-984N3-Methylcytosine + Oxygen + Oxoglutaric acid > Hydrogen ion + Cytosine + Carbon dioxide + Formaldehyde + Succinic acidRXN0-9851-Ethyladenine + Oxygen + Oxoglutaric acid > Adenine + Carbon dioxide + Acetaldehyde + Succinic acidRXN0-986Hydrogen ion + Superoxide anion > Hydrogen peroxide + OxygenSUPEROX-DISMUT-RXNDNA-base-CH(3) + Oxoglutaric acid + Oxygen > DNA-base + Formaldehyde + Succinic acid + Carbon dioxideRCH(2)NH(2) + Water + Oxygen > RCHO + Ammonia + Hydrogen peroxidePhenylethylamine + Water + Oxygen > Phenylacetaldehyde + Ammonia + Hydrogen peroxide2 Hydrogen peroxide > Oxygen +2 WaterUbiquinol-8 + Oxygen > Ubiquinone-8 + WaterHydrocinnamic acid + NADH + Oxygen > cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NADR06782HCAMULTI-RXNtrans-Cinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + NADCoproporphyrinogen III + Oxygen + 2 Hydrogen ion > Protoporphyrinogen IX +2 Carbon dioxide +2 WaterRXN0-14612 Nitric oxide + 2 Oxygen + NAD(P)H >2 Nitrate + NAD(P)(+)(S)-2-hydroxy acid + Oxygen > 2-oxo acid + Hydrogen peroxide3-(3-Hydroxyphenyl)propanoic acid + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propanoate + Water + NAD3-Hydroxycinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NAD3-(2,3-Dihydroxyphenyl)propanoate + Oxygen > 2-Hydroxy-6-oxonona-2,4-diene-1,9-dioateTrans-2,3-Dihydroxycinnamate + Oxygen > 2-Hydroxy-6-ketononatrienedioateN-methyl-L-tryptophan + Water + Oxygen > L-Tryptophan + Formaldehyde + Hydrogen peroxideL-Aspartic acid + Oxygen > Iminoaspartic acid + Hydrogen peroxidePhenylacetyl-CoA + NADPH + Oxygen > 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + WaterPyridoxamine 5'-phosphate + Water + Oxygen > Pyridoxal 5'-phosphate + Ammonia + Hydrogen peroxidegamma-Glutamyl-L-putrescine + Water + Oxygen > Gamma-glutamyl-gamma-aminobutyraldehyde + Ammonia + Hydrogen peroxideUracil + FMNH(2) + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + WaterThymine + FMNH(2) + Oxygen > (Z)-2-Methyl-ureidoacrylate peracid + Flavin Mononucleotide + Water2 superoxide + 2 Hydrogen ion > Oxygen + Hydrogen peroxideAn alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + Oxygen > an aldehyde (R-CHO) + Flavin Mononucleotide + Sulfite + WaterTaurine + Oxoglutaric acid + Oxygen > Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxideQuercetin + Oxygen > 2-(3,4-dihydroxybenzoyloxy)-4,6-dihydroxybenzoate + CO + Hydrogen ion2 Hydrogen ion + 2 superoxide <> Oxygen + Hydrogen peroxideR00275 3-(3-Hydroxyphenyl)propanoic acid + NADH + Hydrogen ion + Oxygen + 3-Hydroxycinnamic acid <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD + Trans-2,3-DihydroxycinnamateR06786 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen + Trans-2,3-Dihydroxycinnamate <> 2-Hydroxy-6-ketononadienedicarboxylate + 2-Hydroxy-6-ketononatrienedioateR04376 NADH + Hydrogen ion + Oxygen + Hydrocinnamic acid <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + Trans-2,3-DihydroxycinnamateR06782 Nitric oxide + 2 Oxygen + NADH + NADPH <>2 Nitrate + NAD + NADP + Hydrogen ionR05724 R05725 Reduced acceptor + Hydrogen peroxide <> Acceptor + Water + OxygenR03532 Alkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + WaterR07210 Uracil + FMNH + Oxygen + Thymine <> Ureidoacrylate peracid + Flavin Mononucleotide + (Z)-2-Methyl-ureidoacrylate peracidR09936 Primary amine + Water + Oxygen <> Aldehyde + Ammonia + Hydrogen peroxideR01853 Pyridoxamine 5'-phosphate + Water + Oxygen + Pyridoxine 5'-phosphate <> Pyridoxal 5'-phosphate + Ammonia + Hydrogen peroxideR00277 (S)-2-Hydroxyacid + Oxygen <> 2-Oxo acid + Hydrogen peroxideR01341 3,4-Dihydroxy-L-phenylalanine + Oxygen <> 4-(L-Alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehydeR02075 Protoporphyrinogen IX + 3 Oxygen <> Protoporphyrin IX +3 Hydrogen peroxideR03222 Taurine + Oxoglutaric acid + Oxygen > Sulfite + Succinic acid + Aminoacetaldehyde + Carbon dioxide + SulfitePW_R002558Taurine + Oxoglutaric acid + Oxygen > Sulfite + Succinic acid + Carbon dioxide + Hydrogen ion + Aminoacetaldehyde + SulfitePW_R003461L-Aspartic acid + Water + Oxygen + L-Aspartic acid > Oxalacetic acid + Ammonia + Hydrogen peroxidePW_R002645L-Aspartic acid + Oxygen + L-Aspartic acid > Hydrogen peroxide + Hydrogen ion + Iminoaspartic acidPW_R003007gamma-Glutamyl-L-putrescine + Oxygen + Water > 4-(γ-glutamylamino)butanal + Ammonium + Hydrogen peroxidePW_R002686L-Phenylalanine + Oxygen + L-Phenylalanine <> Oxoglutaric acid + Phenylpyruvic acidPW_R003456L-Phenylalanine + Oxygen + L-Phenylalanine <> Carbon dioxide + Sinapyl alcoholPW_R003458alkylsulfonate + FMNH2 + Oxygen > Betaine aldehyde + Sulfite + Flavin Mononucleotide + Water +2 Hydrogen ion + SulfitePW_R003462Butanesulfonate + Oxygen + FMNH2 > Hydrogen ion + Water + Sulfite + Flavin Mononucleotide + Betaine aldehyde + SulfitePW_R003467Oxygen + FMNH2 + 3-(N-morpholino)propanesulfonate > Sulfite + Water + Hydrogen ion + Flavin Mononucleotide + Betaine aldehyde + SulfitePW_R003468 ethanesulfonate + Oxygen + FMNH2 > Hydrogen ion + Water + Flavin Mononucleotide + Sulfite + Betaine aldehyde + SulfitePW_R003469 isethionate + Oxygen + FMNH2 > Betaine aldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite + SulfitePW_R003470Oxygen + methanesulfonate + FMNH2 + Methanesulfonate > Hydrogen ion + Water + Flavin Mononucleotide + Sulfite + Betaine aldehyde + SulfitePW_R003471Protoporphyrinogen IX + 3 Oxygen > Protoporphyrin IX +3 Hydrogen peroxidePW_R0034842-Octaprenylphenol + Hydrogen ion + NADPH + Oxygen + NADPH > NADP + Water + 2-Octaprenyl-6-hydroxyphenol + 2-Octaprenyl-6-hydroxyphenolPW_R003718Hydrogen ion + NADPH + Oxygen + 2-methoxy-6-(all-trans-octaprenyl)phenol + NADPH > Water + NADP + 2-Octaprenyl-6-methoxy-1,4-benzoquinolPW_R003720Oxygen + Reduced acceptor + 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol > Water + oxidized electron acceptor + 3-demethylubiquinol-8PW_R0037223-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > NAD + Water + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acidPW_R005155Cinnamic acid + NADH + Oxygen <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NADPW_R003835NADH + Oxygen + 3-phenylpropanoate <> NAD + cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diolPW_R003836NADH + Oxygen + 3-phenylpropanoate <> NAD + Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diolPW_R003837Hydrocinnamic acid + NADH + Oxygen <> NAD + cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diolPW_R0038502-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + Oxygen + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioatePW_R0051582 Ubiquinol-1 + Oxygen + 4 Hydrogen ion >2 Ubiquinone-1 +2 Water +4 Hydrogen ionPW_RCT000140Oxygen + 8 Hydrogen ion + 2 Ubiquinol-1 >2 Water +8 Hydrogen ion +2 Ubiquinone-1PW_RCT0001423-(2,3-Dihydroxyphenyl)propionic acid + Oxygen > (2E,4Z)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + Hydrogen ionPW_R005882Uracil + FMNH2 + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ion + PeroxyaminoacrylatePW_R005905Phenylacetyl-CoA + Hydrogen ion + NADPH + Oxygen > Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoAPW_R005920gamma-Glutamyl-L-putrescine + Oxygen + Hydrogen ion > gamma-Glutamyl-gamma-butyraldehyde + Hydrogen peroxide + AmmoniumPW_R0059982-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + Oxygen + Reduced acceptor > 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + Water + oxidized electron acceptorPW_R005947trans-Cinnamic acid + Hydrogen ion + Oxygen + NADH > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NADPW_R005945Oxygen + 4 Hydrogen ion + Electron >2 WaterPW_R006092Aminoacetone + Oxygen + Water > Hydrogen peroxide + Ammonium + PyruvaldehydePW_R006139Coproporphyrin III + 2 Hydrogen ion + Oxygen <>2 Carbon dioxide +2 Water + Protoporphyrinogen IXL-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acidOxygen + Pyridoxine 5'-phosphate > Hydrogen peroxide + Pyridoxal 5'-phosphate2 Hydrogen peroxide <>2 Water + Oxygengamma-Glutamyl-L-putrescine + Water + Oxygen <> gamma-Glutamyl-gamma-butyraldehyde + Ammonia + Hydrogen peroxideAlkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + WaterOxygen + 4 Fe2+ + 4 Hydrogen ion <>4 Fe3+ +2 Wateralpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acidTaurine + alpha-Ketoglutarate + Oxygen <> Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxide2 Hydrogen ion + 2 superoxide <> Oxygen + Hydrogen peroxide2 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <>2 2-Octaprenyl-6-hydroxyphenol + NADP + Water2 2-Polyprenyl-6-methoxyphenol + Oxygen <>2 2-Polyprenyl-6-methoxy-1,4-benzoquinone + WaterGlycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxideL-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acidOxygen + Pyridoxine 5'-phosphate > Hydrogen peroxide + Pyridoxal 5'-phosphateOxygen + 4 Fe2+ + 4 Hydrogen ion <>4 Fe3+ +2 Wateralpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acid2 Hydrogen ion + 2 superoxide <> Oxygen + Hydrogen peroxide2 2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <>2 2-Octaprenyl-6-hydroxyphenol + NADP + WaterGlycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxideGlycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide