1.0 2011-09-21 00:20:44 UTC 2015-07-21 06:57:24 UTC FDB022862 trans-3-Decenoyl-CoA trans-3-Decenoyl-CoA is an intermediate in fatty acid metabolism. trans-3-Decenoyl-CoA is the substrate of medium-chain acyl-CoA dehydrogenase (MCAD, EC 1.3.99.3) MCAD acts on C4-C16 acyl-CoAs with its peak activity toward medium-chain (C6-C12) substrates. MCAD is a key enzyme for the beta-oxidation of fatty acids. MCAD deficiency is caused by mutation in the medium-chain acyl-CoA dehydrogenase gene (ACADM; OMIM 607008). Inherited deficiency of medium-chain acyl-CoA dehydrogenase is characterized by intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels. The disorder may be severe, and even fatal, in young patients. It has been reported that between 19 and 25% of patients with undiagnosed deficiency of MCAD die during their first episode of metabolic decompensation. (PMID: 15850406) [HMDB] (E)-S-3-decenoate (E)-S-3-decenoate CoA (E)-S-3-decenoate Coenzyme A (E)-S-3-decenoic acid 3-trans-Decenoyl-CoA 3-trans-Decenoyl-Coenzyme A S-(3E)-3-decenoate S-(3E)-3-decenoateCoA S-(3E)-3-decenoateCoenzyme A S-(3E)-3-decenoic acid trans-3-Decenoyl-CoA trans-3-Decenoyl-Coenzyme A trans-Dec-3-enoyl-coenzyme A C31H52N7O17P3S 919.768 919.235323499 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(3E)-dec-3-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid 3-trans-decenoyl-coa 6410-54-4 CCCCCC\C=C\CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 InChI=1S/C31H52N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h9-10,18-20,24-26,30,41-42H,4-8,11-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b10-9+/t20-,24-,25-,26+,30-/m1/s1 CQGVNMQHZQJNII-ZJZQAHHTSA-N belongs to the class of organic compounds known as 3-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 3-enoyl chain. 3-enoyl CoAs Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acyl thioesters Aromatic heteropolycyclic compounds 6-aminopurines Acyl CoAs Aminopyrimidines and derivatives Azacyclic compounds Beta amino acids and derivatives Carbonyl compounds Carbothioic S-esters Coenzyme A and derivatives Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Monoalkyl phosphates Monosaccharide phosphates N-acyl amines N-substituted imidazoles Organic oxides Organic pyrophosphates Organopnictogen compounds Oxacyclic compounds Pentose phosphates Primary amines Purine ribonucleoside diphosphates Ribonucleoside 3'-phosphates Secondary alcohols Secondary carboxylic acid amides Sulfenyl compounds Tetrahydrofurans Thioesters 6-aminopurine Alcohol Alkyl phosphate Amine Amino acid or derivatives Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Beta amino acid or derivatives Carbonyl group Carbothioic s-ester Carboxamide group Carboxylic acid derivative Coenzyme a or derivatives Fatty amide Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Imidazole Imidazopyrimidine Imidolactam Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-acyl-amine N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Oxacycle Pentose monosaccharide Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary amine Purine Purine ribonucleoside 3',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Pyrimidine Ribonucleoside 3'-phosphate Secondary alcohol Secondary carboxylic acid amide Sulfenyl compound Tetrahydrofuran Thiocarboxylic acid ester Thiocarboxylic acid or derivatives medium-chain fatty acyl-CoA trans-3-enoyl-CoA Solid logp 0.99 ALOGPS logs -2.52 ALOGPS solubility 2.76e+00 g/l ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 0.83 ChemAxon pka_strongest_basic 4.95 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(3E)-dec-3-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 919.768 ChemAxon mono_mass 919.235323499 ChemAxon smiles CCCCCC\C=C\CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 ChemAxon formula C31H52N7O17P3S ChemAxon inchi InChI=1S/C31H52N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h9-10,18-20,24-26,30,41-42H,4-8,11-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b10-9+/t20-,24-,25-,26+,30-/m1/s1 ChemAxon inchikey CQGVNMQHZQJNII-ZJZQAHHTSA-N ChemAxon polar_surface_area 363.63 ChemAxon refractivity 210.16 ChemAxon polarizability 85.92 ChemAxon rotatable_bond_count 27 ChemAxon acceptor_count 17 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 287815 Specdb::MsMs 287816 Specdb::MsMs 287817 Specdb::MsMs 326752 Specdb::MsMs 326753 Specdb::MsMs 326754 Specdb::MsMs 2422335 Specdb::MsMs 2422336 Specdb::MsMs 2422337 Specdb::MsMs 2513986 Specdb::MsMs 2513987 Specdb::MsMs 2513988 Specdb::NmrOneD 109538 Specdb::NmrOneD 109539 Specdb::NmrOneD 109540 Specdb::NmrOneD 109541 Specdb::NmrOneD 109542 Specdb::NmrOneD 109543 Specdb::NmrOneD 109544 Specdb::NmrOneD 109545 Specdb::NmrOneD 109546 Specdb::NmrOneD 109547 Specdb::NmrOneD 109548 Specdb::NmrOneD 109549 Specdb::NmrOneD 109550 Specdb::NmrOneD 109551 Specdb::NmrOneD 109552 Specdb::NmrOneD 109553 Specdb::NmrOneD 109554 Specdb::NmrOneD 109555 Specdb::NmrOneD 109556 Specdb::NmrOneD 109557 HMDB02137 29126 #<Reference:0x000055ce30a513e8> #<Reference:0x000055ce30a51230> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823