2.0 2012-05-31 14:34:24 -0600 2015-06-03 17:19:35 -0600 ECMDB20231 M2MDB001076 3-Hydroxyadipyl-CoA 3-hydroxyadipyl-coa belongs to the class of Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. (inferred from compound structure) C27H44N7O20P3S 911.659 911.157467109 6-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4-hydroxy-6-oxohexanoic acid 6-[(2-{[3-({4-[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene}amino)-1-hydroxypropylidene]amino}ethyl)sulfanyl]-4-hydroxy-6-oxohexanoic acid CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(O)=NCCC(O)=NCCSC(=O)CC(O)CCC(O)=O InChI=1S/C27H44N7O20P3S/c1-27(2,22(41)25(42)30-6-5-16(36)29-7-8-58-18(39)9-14(35)3-4-17(37)38)11-51-57(48,49)54-56(46,47)50-10-15-21(53-55(43,44)45)20(40)26(52-15)34-13-33-19-23(28)31-12-32-24(19)34/h12-15,20-22,26,35,40-41H,3-11H2,1-2H3,(H,29,36)(H,30,42)(H,37,38)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45) OTEACGAEDCIMBS-UHFFFAOYSA-N Cytoplasm Periplasm logp -0.60 ALOGPS logs -2.22 ALOGPS solubility 5.53e+00 g/l ALOGPS logp -4.8 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.84 ChemAxon iupac 6-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4-hydroxy-6-oxohexanoic acid ChemAxon average_mass 911.659 ChemAxon mono_mass 911.157467109 ChemAxon smiles CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(O)=NCCC(O)=NCCSC(=O)CC(O)CCC(O)=O ChemAxon formula C27H44N7O20P3S ChemAxon inchi InChI=1S/C27H44N7O20P3S/c1-27(2,22(41)25(42)30-6-5-16(36)29-7-8-58-18(39)9-14(35)3-4-17(37)38)11-51-57(48,49)54-56(46,47)50-10-15-21(53-55(43,44)45)20(40)26(52-15)34-13-33-19-23(28)31-12-32-24(19)34/h12-15,20-22,26,35,40-41H,3-11H2,1-2H3,(H,29,36)(H,30,42)(H,37,38)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45) ChemAxon inchikey OTEACGAEDCIMBS-UHFFFAOYSA-N ChemAxon polar_surface_area 428.14 ChemAxon refractivity 194.86 ChemAxon polarizability 82.46 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 22 ChemAxon donor_count 11 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Phenylethylamine metabolism The 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. PW002027 Metabolic phenylacetate degradation I (aerobic) PWY0-321 Specdb::EiMs 2655 Specdb::NmrOneD 341008 Specdb::NmrOneD 341009 Specdb::NmrOneD 341010 Specdb::NmrOneD 341011 Specdb::NmrOneD 341012 Specdb::NmrOneD 341013 Specdb::NmrOneD 341014 Specdb::NmrOneD 341015 Specdb::NmrOneD 341016 Specdb::NmrOneD 341017 Specdb::NmrOneD 341018 Specdb::NmrOneD 341019 Specdb::NmrOneD 341020 Specdb::NmrOneD 341021 Specdb::NmrOneD 341022 Specdb::NmrOneD 341023 Specdb::NmrOneD 341024 Specdb::NmrOneD 341025 Specdb::NmrOneD 341026 Specdb::NmrOneD 341027 Specdb::MsMs 24773 Specdb::MsMs 24774 Specdb::MsMs 24775 Specdb::MsMs 31331 Specdb::MsMs 31332 Specdb::MsMs 31333 Specdb::MsMs 3595264 Specdb::MsMs 3595265 Specdb::MsMs 3595266 Specdb::MsMs 3595267 Specdb::MsMs 3595268 Specdb::MsMs 3595269 90 88 3-HYDROXYADIPYL-COA Keseler, 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. 21097882 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Probable enoyl-CoA hydratase paaF P76082 PAAF_ECOLI paaF http://ecmdb.ca/proteins/P76082.xml Probable 3-hydroxybutyryl-CoA dehydrogenase P76083 PAAH_ECOLI paaH http://ecmdb.ca/proteins/P76083.xml Probable enoyl-CoA hydratase paaG P77467 PAAG_ECOLI paaG http://ecmdb.ca/proteins/P77467.xml 3-Hydroxyadipyl-CoA + NAD <> Hydrogen ion + 3-Oxoadipyl-CoA + NADH RXN0-2044 3-Hydroxyadipyl-CoA <> 2,3-dehydroadipyl-CoA + Water RXN0-6513 2,3-didehydroadipyl-CoA + Water > 3-Hydroxyadipyl-CoA PW_R005924 3-Hydroxyadipyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxoadipyl-CoA PW_R005925