2.02012-05-31 14:34:24 -06002015-06-03 17:19:35 -0600ECMDB20231M2MDB0010763-Hydroxyadipyl-CoA3-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)C27H44N7O20P3S911.659911.1574671096-({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 acid6-[(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 acidCC(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)=OInChI=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-NCytoplasmPeriplasmlogp-0.60logs-2.22solubility5.53e+00 g/llogp-4.8pka_strongest_acidic0.82pka_strongest_basic4.84iupac6-({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 acidaverage_mass911.659mono_mass911.157467109smilesCC(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)=OformulaC27H44N7O20P3SinchiInChI=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)inchikeyOTEACGAEDCIMBS-UHFFFAOYSA-Npolar_surface_area428.14refractivity194.86polarizability82.46rotatable_bond_count25acceptor_count22donor_count11physiological_charge-4formal_charge0Phenylethylamine 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.PW002027Metabolicphenylacetate degradation I (aerobic)PWY0-321Specdb::EiMs2655Specdb::NmrOneD341008Specdb::NmrOneD341009Specdb::NmrOneD341010Specdb::NmrOneD341011Specdb::NmrOneD341012Specdb::NmrOneD341013Specdb::NmrOneD341014Specdb::NmrOneD341015Specdb::NmrOneD341016Specdb::NmrOneD341017Specdb::NmrOneD341018Specdb::NmrOneD341019Specdb::NmrOneD341020Specdb::NmrOneD341021Specdb::NmrOneD341022Specdb::NmrOneD341023Specdb::NmrOneD341024Specdb::NmrOneD341025Specdb::NmrOneD341026Specdb::NmrOneD341027Specdb::MsMs24773Specdb::MsMs24774Specdb::MsMs24775Specdb::MsMs31331Specdb::MsMs31332Specdb::MsMs31333Specdb::MsMs3595264Specdb::MsMs3595265Specdb::MsMs3595266Specdb::MsMs3595267Specdb::MsMs3595268Specdb::MsMs359526990883-HYDROXYADIPYL-COAKeseler, 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-D590.21097882van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Probable enoyl-CoA hydratase paaFP76082PAAF_ECOLIpaaFhttp://ecmdb.ca/proteins/P76082.xmlProbable 3-hydroxybutyryl-CoA dehydrogenaseP76083PAAH_ECOLIpaaHhttp://ecmdb.ca/proteins/P76083.xmlProbable enoyl-CoA hydratase paaGP77467PAAG_ECOLIpaaGhttp://ecmdb.ca/proteins/P77467.xml3-Hydroxyadipyl-CoA + NAD <> Hydrogen ion + 3-Oxoadipyl-CoA + NADHRXN0-20443-Hydroxyadipyl-CoA <> 2,3-dehydroadipyl-CoA + WaterRXN0-65132,3-didehydroadipyl-CoA + Water > 3-Hydroxyadipyl-CoAPW_R0059243-Hydroxyadipyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxoadipyl-CoAPW_R005925