2.0 2012-05-31 13:57:08 -0600 2015-09-13 12:56:12 -0600 ECMDB02812 M2MDB000466 alpha-Ketoglutarate Alpha-ketoglutarate is a member of the chemical class known as Gamma Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Alpha-ketoglutarate is invovled in pentose and glucuronate interconversions, C5-Branched dibasic acid metabolism, Vitamin B6 metabolism, alanine, aspartate and glutamate metabolism, Butanoate metabolism, Glyoxylate and dicarboxylate metabolism, Carbon fixation pathways in prokaryotes, Lysine biosynthesis, Biosynthesis of terpenoids and steroids, and the Citrate cycle (TCA cycle). Alpha-Ketoglutaric acid is one of two ketone derivatives of glutaric acid. (The term ketoglutaric acid, when not further qualified, almost always refers to the alpha variant. Alpha-Ketoglutaric acid varies only by the position of the ketone functional group, and is much less common. Its anion, alpha-ketoglutarate (alpha-KG, also called oxo-glutarate) is an important biological compound. It is the keto acid produced by de-amination of glutamate, and is an intermediate in the Krebs cycle. (WikiPedia) 2-Ketoglutarate 2-Ketoglutaric acid 2-OG 2-Oxo-1,5-pentanedioate 2-Oxo-1,5-pentanedioic acid 2-Oxoglutarate 2-Oxoglutarate(2-) 2-Oxoglutaric acid 2-Oxoglutaric acid(2-) 2-Oxopentanedioate 2-Oxopentanedioate, ion(2-) 2-Oxopentanedioic acid 2-Oxopentanedioic acid, ion(2-) a-Ketoglutarate a-Ketoglutaric acid Alpha-Ketoglutarate Alpha-Ketoglutaric acid Oxoglutarate Oxoglutaric acid Pentanedioate, 2-oxo-, ion(2-) Pentanedioic acid, 2-oxo-, ion(2-) α-Ketoglutarate α-Ketoglutaric acid C5H4O5 144.0823 144.005873238 2-oxopentanedioate α ketoglutarate [O-]C(=O)CCC(=O)C([O-])=O InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/p-2 KPGXRSRHYNQIFN-UHFFFAOYSA-L Cytosol Extra-organism Periplasm logp -0.45 ALOGPS logs -0.50 ALOGPS solubility 5.65e+01 g/l ALOGPS logp -0.11 ChemAxon pka_strongest_acidic 2.66 ChemAxon pka_strongest_basic -9.7 ChemAxon iupac 2-oxopentanedioate ChemAxon average_mass 144.0823 ChemAxon mono_mass 144.005873238 ChemAxon smiles [O-]C(=O)CCC(=O)C([O-])=O ChemAxon formula C5H4O5 ChemAxon inchi InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/p-2 ChemAxon inchikey KPGXRSRHYNQIFN-UHFFFAOYSA-L ChemAxon polar_surface_area 97.33 ChemAxon refractivity 50.56 ChemAxon polarizability 11.32 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 0 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Glutathione metabolism The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione. This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione. PW000833 ec00480 Metabolic Citrate cycle (TCA cycle) ec00020 Butanoate metabolism ec00650 Reductive carboxylate cycle (CO2 fixation) ec00720 Alanine, aspartate and glutamate metabolism ec00250 Arginine and proline metabolism ec00330 Nitrogen 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. PW000755 ec00910 Metabolic Cysteine and methionine metabolism ec00270 Tyrosine metabolism ec00350 Phenylalanine metabolism The 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. PW000921 ec00360 Metabolic Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Novobiocin biosynthesis ec00401 Carbon fixation in photosynthetic organisms ec00710 Isoquinoline alkaloid biosynthesis ec00950 Tropane, piperidine and pyridine alkaloid biosynthesis ec00960 Glycine, serine and threonine metabolism ec00260 Ascorbate and aldarate metabolism ec00053 Amino sugar and nucleotide sugar metabolism ec00520 Lysine biosynthesis Lysine is biosynthesized from L-aspartic acid. L-aspartic acid can be incorporated into the cell through various methods: C4 dicarboxylate / orotate:H+ symporter , glutamate / aspartate : H+ symporter GltP, dicarboxylate transporter , C4 dicarboxylate / C4 monocarboxylate transporter DauA, glutamate / aspartate ABC transporter L-aspartic acid is phosphorylated by an ATP-driven Aspartate kinase resulting in ADP and L-aspartyl-4-phosphate. L-aspartyl-4-phosphate is then dehydrogenated through an NADPH driven aspartate semialdehyde dehydrogenase resulting in a release of phosphate, NADP and L-aspartic 4-semialdehyde (involved in methionine biosynthesis). L-aspartic 4-semialdehyde interacts with a pyruvic acid through a 4-hydroxy-tetrahydrodipicolinate synthase resulting in a release of hydrogen ion, water and (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate. The latter compound is then reduced by an NADPH driven 4-hydroxy-tetrahydrodipicolinate reductase resulting in a release of water, NADP and (S)-2,3,4,5-tetrahydrodipicolinate, This compound interacts with succinyl-CoA and water through a tetrahydrodipicolinate succinylase resulting in a release of coenzyme A and N-Succinyl-2-amino-6-ketopimelate. This compound interacts with L-glutamic acid through a N-succinyldiaminopimelate aminotransferase resulting in oxoglutaric acid, N-succinyl-L,L-2,6-diaminopimelate. The latter compound is then desuccinylated by reacting with water through a N-succinyl-L-diaminopimelate desuccinylase resulting in a succinic acid and L,L-diaminopimelate. This compound is then isomerized through a diaminopimelate epimerase resulting in a meso-diaminopimelate (involved in peptidoglyccan biosynthesis I). This compound is then decarboxylated by a diaminopimelate decarboxylase resulting in a release of carbon dioxide and L-lysine. L-lysine is then incorporated into lysine degradation pathway. Lysine also regulate its own biosynthesis by repressing dihydrodipicolinate synthase and also repressing lysine-sensitive aspartokinase 3. A metabolic connection joins synthesis of an amino acid, lysine, to synthesis of cell wall material. Diaminopimelate is a precursor both for lysine and for cell wall components. The synthesis of lysine, methionine and threonine share two reactions at the start of the three pathways, the reactions converting L-aspartate to L-aspartate semialdehyde. The reaction involving aspartate kinase is carried out by three isozymes, one specific for synthesis of each end product amino acid. Each of the three aspartate kinase isozymes is regulated by its corresponding end product amino acid. PW000771 ec00300 Metabolic Methane metabolism ec00680 Valine, leucine and isoleucine biosynthesis ec00290 C5-Branched dibasic acid metabolism ec00660 Pantothenate and CoA biosynthesis The CoA biosynthesis requires compounds from two other pathways: aspartate metabolism and valine biosynthesis. It requires a Beta-Alanine and R-pantoate. The compound (R)-pantoate is generated in two reactions, as shown by the interaction of alpha-ketoisovaleric acid, 5,10 methylene-THF and water through a 3-methyl-2-oxobutanoate hydroxymethyltransferase resulting in a tetrahydrofolic acid and a 2-dehydropantoate. This compound interacts with hydrogen through a NADPH driven acetohydroxy acid isomeroreductase resulting in the release of NADP and R-pantoate. On the other hand L-aspartic acid interacts with a hydrogen ion and gets decarboxylated through an Aspartate 1- decarboxylase resulting in a carbon dioxide and a Beta-alanine. Beta-alanine and R-pantoate interact with an ATP driven pantothenate synthetase resulting in pyrophosphate, AMP, hydrogen ion and pantothenic acid. Pantothenic acid is phosphorylated through a ATP-driven pantothenate kinase resulting in a ADP, a hydrogen ion and D-4'-Phosphopantothenate. This compound interacts with a CTP and a L-cysteine resulting in a fused 4'-phosphopantothenoylcysteine decarboxylase and phosphopantothenoylcysteine synthetase resulting in a hydrogen ion, a pyrophosphate, a CMP and 4-phosphopantothenoylcysteine. The latter compound interacts with a hydrogen ion through a fused 4'-phosphopantothenoylcysteine decarboxylase and phosphopantothenoylcysteine synthetase resulting in a carbon dioxide release and a 4-phosphopantetheine. This compound interacts with an ATP, hydrogen ion and an phosphopantetheine adenylyltransferase resulting in a release of pyrophosphate, and dephospho-CoA. Dephospho-CoA reacts with an ATP driven dephospho-CoA kinase resulting in a ADP , a hydrogen ion and a Coenzyme A. . The latter is converted into (R)-4'-phosphopantothenate is two steps, involving a β-alanine ligase and a kinase. In most organsims the ligase acts before the kinase (EC 6.3.2.1, pantoate—β-alanine ligase (AMP-forming) followed by EC 2.7.1.33, pantothenate kinase, as described in phosphopantothenate biosynthesis I and phosphopantothenate biosynthesis II. However, in archaea the order is reversed, and EC 2.7.1.169, pantoate kinase acts before EC 6.3.2.36, 4-phosphopantoate—β-alanine ligase, as described in phosphopantothenate biosynthesis III. The kinases are feedback inhibited by CoA itself, accounting for the primary regulatory mechanism of CoA biosynthesis. The addition of L-cysteine to (R)-4'-phosphopantothenate, resulting in the formation of R-4'-phosphopantothenoyl-L-cysteine (PPC), is followed by decarboxylation of PPC to 4'-phosphopantetheine. The ultimate reaction is catalyzed by EC 2.7.1.24, dephospho-CoA kinase, which converts 4'-phosphopantetheine to CoA. All enzymes of this pathway are essential for growth. The reactions in the biosynthetic route towards CoA are identical in most organisms, although there are differences in the functionality of the involved enzymes. In plants every step is catalyzed by single monofunctional enzymes, whereas in bacteria and mammals bifunctional enzymes are often employed [Rubio06]. PW000828 ec00770 Metabolic Vitamin B6 metabolism ec00750 Sulfur metabolism 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 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. PW000922 ec00920 Metabolic Pentose and glucuronate interconversions ec00040 Tryptophan metabolism The 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 PW000815 ec00380 Metabolic Glyoxylate and dicarboxylate metabolism ec00630 Histidine metabolism ec00340 beta-Alanine metabolism The 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. PW000896 ec00410 Metabolic Propanoate metabolism Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA. Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate. Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid. Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA. ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid. Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA. PW000940 ec00640 Metabolic Taurine and hypotaurine metabolism ec00430 D-Glutamine and D-glutamate metabolism L-glutamine is transported into the cytoplasm through a glutamine ABC transporter. Once inside, L-glutamine is metabolized with glutaminase to produce an L-glutamic acid. This process can be reversed through a glutamine synthetase resulting in L-glutamine. L-glutamic acid can also be transported into the cytoplasm through various methods: a glutamate/aspartate:H+ symporter GltP, a glutamate: sodium symporter or a glutamate/aspartate ABC transporter. L-glutamic acid can proceed to L-glutamate metabolism or it can undergo a reversible reaction through a glutamate racemase resulting in D-glutamic acid. This compound can also be obtained from D-glutamine interacting with a glutaminase. D-glutamic acid reacts with UDP-N-acetylmuramoyl-L-alanine through an ATP driven UDP-N-acetylmuramoylalanine-D-glutamate ligase resulting in a UDP-N-acetylmuramoyl-L-alanyl-D-glutamate which is then integrated into the peptidoglycan biosynthesis UDP-N-acetylmuramoyl-L-alanine comes from the amino sugar and nucleotide sugar metabolism product, UDP-N-acetylmuraminate which reacts with L-alanine through an ATP-driven UDP-N-acetylmuramate-L-alanine ligase. PW000769 ec00471 Metabolic Lysine degradation ec00310 Valine, leucine and isoleucine degradation ec00280 Ubiquinone and other terpenoid-quinone biosynthesis ec00130 Microbial metabolism in diverse environments ec01120 Glucosinolate biosynthesis ec00966 Metabolic pathways eco01100 Specdb::NmrOneD 337468 Specdb::NmrOneD 337469 Specdb::NmrOneD 337470 Specdb::NmrOneD 337471 Specdb::NmrOneD 337472 Specdb::NmrOneD 337473 Specdb::NmrOneD 337474 Specdb::NmrOneD 337475 Specdb::NmrOneD 337476 Specdb::NmrOneD 337477 Specdb::NmrOneD 337478 Specdb::NmrOneD 337479 Specdb::NmrOneD 337480 Specdb::NmrOneD 337481 Specdb::NmrOneD 337482 Specdb::NmrOneD 337483 Specdb::NmrOneD 337484 Specdb::NmrOneD 337485 Specdb::NmrOneD 337486 Specdb::NmrOneD 337487 Specdb::MsMs 28508 Specdb::MsMs 28509 Specdb::MsMs 28510 Specdb::MsMs 35066 Specdb::MsMs 35067 Specdb::MsMs 35068 HMDB00208 144236 C00026 16810 Oxoglutarate Kanehisa, 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. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 http://hmdb.ca/system/metabolites/msds/000/000/146/original/HMDB00208.pdf?1358461800 NADP-specific glutamate dehydrogenase P00370 DHE4_ECOLI gdhA http://ecmdb.ca/proteins/P00370.xml Aspartate aminotransferase P00509 AAT_ECOLI aspC http://ecmdb.ca/proteins/P00509.xml Aromatic-amino-acid aminotransferase P04693 TYRB_ECOLI tyrB http://ecmdb.ca/proteins/P04693.xml Histidinol-phosphate aminotransferase P06986 HIS8_ECOLI hisC http://ecmdb.ca/proteins/P06986.xml Isocitrate dehydrogenase [NADP] P08200 IDH_ECOLI icd http://ecmdb.ca/proteins/P08200.xml Glutamate synthase [NADPH] large chain P09831 GLTB_ECOLI gltB http://ecmdb.ca/proteins/P09831.xml Glutamate synthase [NADPH] small chain P09832 GLTD_ECOLI gltD http://ecmdb.ca/proteins/P09832.xml Dihydrolipoyl dehydrogenase P0A9P0 DLDH_ECOLI lpdA http://ecmdb.ca/proteins/P0A9P0.xml 2-oxoglutarate dehydrogenase E1 component P0AFG3 ODO1_ECOLI sucA http://ecmdb.ca/proteins/P0AFG3.xml Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex P0AFG6 ODO2_ECOLI sucB http://ecmdb.ca/proteins/P0AFG6.xml 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase P17109 MEND_ECOLI menD http://ecmdb.ca/proteins/P17109.xml Acetylornithine/succinyldiaminopimelate aminotransferase P18335 ARGD_ECOLI argD http://ecmdb.ca/proteins/P18335.xml 4-aminobutyrate aminotransferase P22256 GABT_ECOLI gabT http://ecmdb.ca/proteins/P22256.xml Phosphoserine aminotransferase P23721 SERC_ECOLI serC http://ecmdb.ca/proteins/P23721.xml Alpha-ketoglutarate-dependent taurine dioxygenase P37610 TAUD_ECOLI tauD http://ecmdb.ca/proteins/P37610.xml Putrescine aminotransferase P42588 PAT_ECOLI patA http://ecmdb.ca/proteins/P42588.xml 4-aminobutyrate aminotransferase_ P50457 PUUE_ECOLI puuE http://ecmdb.ca/proteins/P50457.xml Succinylornithine transaminase P77581 ASTC_ECOLI astC http://ecmdb.ca/proteins/P77581.xml UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase P77690 ARNB_ECOLI arnB http://ecmdb.ca/proteins/P77690.xml Uncharacterized aminotransferase yfbQ P0A959 YFBQ_ECOLI yfbQ http://ecmdb.ca/proteins/P0A959.xml Branched-chain-amino-acid aminotransferase P0AB80 ILVE_ECOLI ilvE http://ecmdb.ca/proteins/P0AB80.xml Lipopolysaccharide biosynthesis protein rffA P27833 RFFA_ECOLI rffA http://ecmdb.ca/proteins/P27833.xml Uncharacterized aminotransferase yfdZ P77434 YFDZ_ECOLI yfdZ http://ecmdb.ca/proteins/P77434.xml Alpha-ketoglutarate permease P0AEX3 KGTP_ECOLI kgtP http://ecmdb.ca/proteins/P0AEX3.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml alpha-Ketoglutarate + Coenzyme A + NAD > Carbon dioxide + NADH + Succinyl-CoA N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate R02283 alpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid R00258 gamma-Aminobutyric acid + alpha-Ketoglutarate <> L-Glutamate + Succinic acid semialdehyde R01648 alpha-Ketoglutarate + L-Glutamine + Hydrogen ion + NADPH >2 L-Glutamate + NADP R00114 Ketoleucine + L-Glutamate > alpha-Ketoglutarate + L-Leucine alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid R00694 alpha-Ketoglutarate + L-Tyrosine <> 4-Hydroxyphenylpyruvic acid + L-Glutamate R00734 alpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acid R05320 L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid <> alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine R05085 Phosphohydroxypyruvic acid + L-Glutamate > alpha-Ketoglutarate + Phosphoserine R04173 alpha-Ketoglutarate + L-Aspartic acid <> L-Glutamate + Oxalacetic acid R00355 Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH R00267 alpha-Ketoglutarate + N2-Succinyl-L-ornithine <> L-Glutamate + N2-Succinyl-L-glutamic acid 5-semialdehyde R04217 L-Glutamate + Water + NADP <> alpha-Ketoglutarate + Hydrogen ion + NADPH + Ammonium L-Glutamate + Imidazole acetol-phosphate <> alpha-Ketoglutarate + Histidinol phosphate R03243 L-Glutamate + UDP-4-Keto-pyranose <> alpha-Ketoglutarate + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose R07659 alpha-Ketoglutarate + Hydrogen ion + Isochorismate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide R08165 alpha-Ketoglutarate + Putrescine > 4-Aminobutyraldehyde + L-Glutamate R01155 alpha-Ketoglutarate + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelate R04475 alpha-Ketoglutarate + L-Isoleucine <> 3-Methyl-2-oxovaleric acid + L-Glutamate R02199 alpha-Ketoglutarate + L-Valine <> alpha-Ketoisovaleric acid + L-Glutamate R01214 4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate > alpha-Ketoglutarate + dTDP-D-Fucosamine 2 L-Glutamate + NAD <> L-Glutamine + alpha-Ketoglutarate + NADH + Hydrogen ion R00093 2 L-Glutamate + NADP <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ion R00114 L-Glutamate + NAD + Water <> alpha-Ketoglutarate + Ammonia + NADH + Hydrogen ion R00243 L-Glutamate + NADP + Water <> alpha-Ketoglutarate + Ammonia + NADPH + Hydrogen ion R00248 Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion R00267 Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide R00268 alpha-Ketoglutarate + Thiamine pyrophosphate <> 3-carboxy-1-hydroxypropylthiamine diphosphate + Carbon dioxide R00621 L-Cysteine + alpha-Ketoglutarate <> 3-Mercaptopyruvic acid + DL-Glutamic acid R00896 beta-Alanine + alpha-Ketoglutarate <> Malonic semialdehyde + L-Glutamate R00908 L-Leucine + alpha-Ketoglutarate <> 4-Methyl-2-oxopentanoate + L-Glutamate + Ketoleucine R01090 Putrescine + alpha-Ketoglutarate <> 4-Aminobutyraldehyde + L-Glutamate R01155 Cysteic acid + alpha-Ketoglutarate <> 3-Sulfopyruvic acid + L-Glutamate R02433 3-Sulfinoalanine + alpha-Ketoglutarate <> 3-Sulfinylpyruvic acid + L-Glutamate R02619 Histidinol phosphate + alpha-Ketoglutarate <> Imidazole acetol-phosphate + L-Glutamate R03243 Phosphoserine + alpha-Ketoglutarate <> Phosphohydroxypyruvic acid + L-Glutamate R04173 (S)-b-aminoisobutyric acid + alpha-Ketoglutarate <> (S)-Methylmalonic acid semialdehyde + L-Glutamate R04188 L-erythro-4-Hydroxyglutamate + alpha-Ketoglutarate <> D-4-Hydroxy-2-oxoglutarate + L-Glutamate R05052 O-Phospho-4-hydroxy-L-threonine + alpha-Ketoglutarate <> 2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamate R05085 Taurine + alpha-Ketoglutarate + Oxygen <> Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxide R05320 2-Oxo-4-methylthiobutanoic acid + L-Glutamate <> L-Methionine + alpha-Ketoglutarate R07396 Isochorismate + alpha-Ketoglutarate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide R08165 alpha-Ketoglutarate <> [Dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine + Carbon dioxide R01700 Phosphoserine + alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine <> Phosphohydroxypyruvic acid + L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid R04173 Ethylenediamine + alpha-Ketoglutarate + 4-Aminobutyraldehyde <> 1-Pyrroline + L-Glutamate + Water R10064 2 L-Glutamate + NADP + Ammonia + Water <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ion R00114 dTDP-D-Fucosamine + alpha-Ketoglutarate <> 4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate R04438 Aromatic amino acid + alpha-Ketoglutarate <> Aromatic oxo acid + L-Glutamate R03120 3-Phospho-D-glycerate + NAD + D-2-Hydroxyglutaric acid <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion + alpha-Ketoglutarate R01513 Isocitric acid + NADP + Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion R00267 gamma-Aminobutyric acid + alpha-Ketoglutarate <> L-Glutamate + Succinic acid semialdehyde beta-Alanine + alpha-Ketoglutarate <> Malonic semialdehyde + L-Glutamate N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate alpha-Ketoglutarate + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelate Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH alpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid L-Glutamate + 2 2-Oxo-3-hydroxy-4-phosphobutanoic acid <> alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine L-Glutamate + UDP-4-Keto-pyranose <> alpha-Ketoglutarate + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose alpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acid Taurine + alpha-Ketoglutarate + Oxygen <> Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxide L-Glutamate + NAD + Water <> alpha-Ketoglutarate + Ammonia + NADH + Hydrogen ion alpha-Ketoglutarate + L-Isoleucine <>3 3-Methyl-2-oxovaleric acid + L-Glutamate alpha-Ketoglutarate + L-Glutamine + Hydrogen ion + NADPH >2 L-Glutamate + NADP gamma-Aminobutyric acid + alpha-Ketoglutarate <> L-Glutamate + Succinic acid semialdehyde Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH alpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid Phosphohydroxypyruvic acid + L-Glutamate > alpha-Ketoglutarate + Phosphoserine alpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acid alpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid 2 L-Glutamate + NAD <> L-Glutamine + alpha-Ketoglutarate + NADH + Hydrogen ion alpha-Ketoglutarate + L-Glutamine + Hydrogen ion + NADPH >2 L-Glutamate + NADP