2.0 2012-08-15 08:51:30 -0600 2015-07-07 11:41:01 -0600 ECMDB21646 M2MDB002040 Aldehyde A dialdehyde is an organic chemical compound with two aldehyde groups. The nomenclature of dialdehydes have the ending -dial or sometimes -dialdehyde. Short aliphatic dialdehydes are sometimes named after the diacid from which they can de derived. An example is butanedial, which is also called succinaldehyde (from succinic acid).; Aldehydes are readily identified by spectroscopic methods. Using IR spectroscopy, they display a strong νCO band near 1700 cm−1. In their 1H NMR spectra, the formyl hydrogen center absorbs near δ9, which is a distinctive part of the spectrum. This signal shows the characteristic coupling to any protons on the alpha carbon.; An aldehyde ( /ˈældɨhaɪd/) is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center (a carbon double bonded to oxygen) bonded to hydrogen and an R group, which is any generic alkyl or side chain. The group without R is called the aldehyde group or formyl group. Aldehydes differ from ketones in that the carbonyl is placed at the end of a carbon skeleton rather than between two carbon atoms. Aldehydes are common in organic chemistry. Many fragrances are aldehydes. Aldehido Aldehidos Aldehyd Aldehyde Aldehydes Aldehydum An aldehyde Formaldehyde Formalin Methanal Methylene oxide Oxomethane Oxomethylene RC(2O)H C20H30O5 350.4492 350.20932407 (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-20-oxoicosa-6,8,10,14-tetraenoic acid 20-aldehyde leukotriene B4 72379-22-7 O[C@@H](CCCC(O)=O)\C=C/C=C/C=C/[C@H](O)C\C=C/CCCCC=O InChI=1S/C20H30O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,17-19,22-23H,1-2,6,10-12,15-16H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1 LVLQYGYNBVIONY-PSPARDEHSA-N Membrane logp 3.53 ALOGPS logs -4.12 ALOGPS solubility 2.64e-02 g/l ALOGPS logp 2.65 ChemAxon pka_strongest_acidic 4.65 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-20-oxoicosa-6,8,10,14-tetraenoic acid ChemAxon average_mass 350.4492 ChemAxon mono_mass 350.20932407 ChemAxon smiles O[C@@H](CCCC(O)=O)\C=C/C=C/C=C/[C@H](O)C\C=C/CCCCC=O ChemAxon formula C20H30O5 ChemAxon inchi InChI=1S/C20H30O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,17-19,22-23H,1-2,6,10-12,15-16H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1 ChemAxon inchikey LVLQYGYNBVIONY-PSPARDEHSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 103.72 ChemAxon polarizability 39.6 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Butanoate metabolism ec00650 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 Isoquinoline alkaloid biosynthesis ec00950 Tropane, piperidine and pyridine alkaloid biosynthesis ec00960 Glycine, serine and threonine metabolism ec00260 Glycolysis / Gluconeogenesis ec00010 Pyruvate metabolism ec00620 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 Glycerolipid metabolism ec00561 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 alpha-Linolenic acid metabolism ec00592 Metabolism of xenobiotics by cytochrome P450 ec00980 Drug metabolism - cytochrome P450 ec00982 Fatty acid metabolism This pathway depicts the degradation of palmitic acid (C16:0). Fatty acid degradation and synthesis are relatively simple processes that are essentially the reverse of each other. The process of fatty acid degradation, also known as Beta-Oxidation, converts an aliphatic compound into a set of activated acetyl units (acetyl CoA) that can be processed by the citric acid cycle. An activated fatty acid is first oxidized to introduce a double bond; the double bond is then hydrated to introduce an oxygen; the alcohol is then oxidized to a ketone; and, finally, the four carbon fragment is cleaved by coenzyme A to yield acetyl CoA and a fatty acid chain two carbons shorter. If the fatty acid has an even number of carbon atoms and is saturated, the process is simply repeated until the fatty acid is completely converted into acetyl CoA units. Fatty acid synthesis is essentially the reverse of this process. Because the result is a polymer, the process starts with monomers—in this case with activated acyl group and malonyl units. The malonyl unit is condensed with the acetyl unit to form a four-carbon fragment. To produce the required hydrocarbon chain, the carbonyl must be reduced. The fragment is reduced, dehydrated, and reduced again, exactly the opposite of degradation, to bring the carbonyl group to the level of a methylene group with the formation of butyryl CoA. Another activated malonyl group condenses with the butyryl unit and the process is repeated until a C16 fatty acid is synthesized. The first step converts the hydroxydecanoyl into a trans 2decenoyl acp through a protein complex conformed of a hydroxomyristoyl dehydratase and a hydroxydecanoyl dehydratase. The second step leads to the production of a cis 3 decenoyl acp through a 3-hydroxydecanoyl acp dehydratase. For the third step the cis 3 decenoyl acp enters a cycle involving a synthase, reductase, dehydratase and an enoyl reductase which in turn produce a cis x enoyl-acp, hydroxy cis x enoyl, trans x-2 cis x enoyl acp and cis x enoyl respectively.This is done until a palmitoleoyl is produce. In said case the pathway procedes in two different directions. It can either produce a palmitoleic acid through a acyl-coa thioesterase, or produce a Vaccenic acid through a different set of reactions. This process is achieved through a 3-oxoacyl acp synthase, a 3-oxoacyl acp reductase, a 3r hydroxymyristoyl dehydratase and an enoyl acp reductase that produces a transition through 3-oxo cis vaccenoyl acp, 3 hydroxy cis vaccenoyl acp, cis vaccen 2 enoyl acp and a cis vaccenoyl acp respectively. At this point it goes through one final reaction to produce a Vaccenic acid, through an acyl-CoA thioesterase PW000796 ec00071 Metabolic 1- and 2-Methylnaphthalene degradation ec00624 3-Chloroacrylic acid degradation ec00641 Retinol metabolism ec00830 Caprolactam degradation ec00930 Microbial metabolism in diverse environments ec01120 Chloroalkane and chloroalkene degradation ec00625 Naphthalene degradation ec00626 Metabolic pathways eco01100 Specdb::CMs 20593 Specdb::CMs 39984 Specdb::CMs 133523 Specdb::CMs 141257 Specdb::NmrOneD 286455 Specdb::NmrOneD 286456 Specdb::NmrOneD 286457 Specdb::NmrOneD 286458 Specdb::NmrOneD 286459 Specdb::NmrOneD 286460 Specdb::NmrOneD 286461 Specdb::NmrOneD 286462 Specdb::NmrOneD 286463 Specdb::NmrOneD 286464 Specdb::NmrOneD 286465 Specdb::NmrOneD 286466 Specdb::NmrOneD 286467 Specdb::NmrOneD 286468 Specdb::NmrOneD 286469 Specdb::NmrOneD 286470 Specdb::NmrOneD 286471 Specdb::NmrOneD 286472 Specdb::NmrOneD 286473 Specdb::NmrOneD 286474 Specdb::MsMs 25451 Specdb::MsMs 25452 Specdb::MsMs 25453 Specdb::MsMs 32009 Specdb::MsMs 32010 Specdb::MsMs 32011 Specdb::MsMs 2373579 Specdb::MsMs 2373580 Specdb::MsMs 2373581 Specdb::MsMs 2564793 Specdb::MsMs 2564794 Specdb::MsMs 2564795 6449839 4952515 C00071 17478 Aldehyde Aldehyde-alcohol dehydrogenase P0A9Q7 ADHE_ECOLI adhE http://ecmdb.ca/proteins/P0A9Q7.xml Gamma-glutamyl-gamma-aminobutyraldehyde dehydrogenase P23883 PUUC_ECOLI puuC http://ecmdb.ca/proteins/P23883.xml S-(hydroxymethyl)glutathione dehydrogenase P25437 FRMA_ECOLI frmA http://ecmdb.ca/proteins/P25437.xml Alcohol dehydrogenase, propanol-preferring P39451 ADHP_ECOLI adhP http://ecmdb.ca/proteins/P39451.xml FMN reductase P80644 SSUE_ECOLI ssuE http://ecmdb.ca/proteins/P80644.xml Alkanesulfonate monooxygenase P80645 SSUD_ECOLI ssuD http://ecmdb.ca/proteins/P80645.xml predicted Fe-containing alcohol dehydrogenase, Pfam00465 family P37686 yiaY http://ecmdb.ca/proteins/P37686.xml Aldehyde + NAD(P)(+) + Water > a carboxylate + NAD(P)H An alcohol + NADP > Aldehyde + NADPH Alkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + Water R07210 Primary amine + Water + Oxygen <> Aldehyde + Ammonia + Hydrogen peroxide R01853 Primary alcohol + NAD + Secondary alcohol <> Aldehyde + NADH + Hydrogen ion + Ketone R00623 Alcohol + NADP <> Aldehyde + NADPH + Hydrogen ion R07328 Alkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + Water