2.0 2012-05-31 14:26:16 -0600 2015-10-15 16:14:29 -0600 ECMDB20077 M2MDB000926 3-Oxoadipyl-CoA 3-oxoadipyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. β-ketoadipyl-CoA 3-Keto-adipyl-coa 3-Ketoadipyl-CoA b-Ketoadipyl-CoA Beta-Ketoadipyl-CoA β-Ketoadipyl-CoA C28H44N7O19P3S 907.67 907.162554393 6-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-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)-4,6-dioxohexanoic acid 6-({2-[(3-{[(2R)-4-[({[(2R,3S,4R,5R)-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)-4,6-dioxohexanoic acid CC(C)(COP(O)(=O)OP(O)(=O)OCC1CC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(=O)CCC(O)=O InChI=1S/C28H44N7O19P3S/c1-28(2,24(42)27(43)31-6-5-18(37)30-7-8-58-20(40)10-16(36)3-4-19(38)39)12-52-57(49,50)54-56(47,48)51-11-15-9-17(22(41)23(15)53-55(44,45)46)35-14-34-21-25(29)32-13-33-26(21)35/h13-15,17,22-24,41-42H,3-12H2,1-2H3,(H,30,37)(H,31,43)(H,38,39)(H,47,48)(H,49,50)(H2,29,32,33)(H2,44,45,46) WQQGFCRVKOMCQC-UHFFFAOYSA-N Cytosol logp -0.31 ALOGPS logs -2.20 ALOGPS solubility 5.68e+00 g/l ALOGPS logp -4.2 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.83 ChemAxon iupac 6-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-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)-4,6-dioxohexanoic acid ChemAxon average_mass 907.67 ChemAxon mono_mass 907.162554393 ChemAxon smiles CC(C)(COP(O)(=O)OP(O)(=O)OCC1CC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(=O)CCC(O)=O ChemAxon formula C28H44N7O19P3S ChemAxon inchi InChI=1S/C28H44N7O19P3S/c1-28(2,24(42)27(43)31-6-5-18(37)30-7-8-58-20(40)10-16(36)3-4-19(38)39)12-52-57(49,50)54-56(47,48)51-11-15-9-17(22(41)23(15)53-55(44,45)46)35-14-34-21-25(29)32-13-33-26(21)35/h13-15,17,22-24,41-42H,3-12H2,1-2H3,(H,30,37)(H,31,43)(H,38,39)(H,47,48)(H,49,50)(H2,29,32,33)(H2,44,45,46) ChemAxon inchikey WQQGFCRVKOMCQC-UHFFFAOYSA-N ChemAxon polar_surface_area 424.98 ChemAxon refractivity 194.04 ChemAxon polarizability 79.62 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 22 ChemAxon donor_count 10 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon 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 Benzoate degradation via hydroxylation ec00362 Caprolactam degradation ec00930 Microbial metabolism in diverse environments ec01120 phenylacetate degradation I (aerobic) PWY0-321 Specdb::NmrOneD 57752 Specdb::NmrOneD 57753 Specdb::NmrOneD 57754 Specdb::NmrOneD 57755 Specdb::NmrOneD 57756 Specdb::NmrOneD 57757 Specdb::NmrOneD 57758 Specdb::NmrOneD 57759 Specdb::NmrOneD 57760 Specdb::NmrOneD 57761 Specdb::NmrOneD 57762 Specdb::NmrOneD 57763 Specdb::NmrOneD 57764 Specdb::NmrOneD 57765 Specdb::NmrOneD 57766 Specdb::NmrOneD 57767 Specdb::NmrOneD 57768 Specdb::NmrOneD 57769 Specdb::NmrOneD 57770 Specdb::NmrOneD 57771 Specdb::MsMs 24728 Specdb::MsMs 24729 Specdb::MsMs 24730 Specdb::MsMs 31286 Specdb::MsMs 31287 Specdb::MsMs 31288 Specdb::MsMs 3225178 Specdb::MsMs 3225179 Specdb::MsMs 3225180 Specdb::MsMs 3225181 Specdb::MsMs 3225182 Specdb::MsMs 3225183 439683 388750 C02232 15490 3-KETO-ADIPYL-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 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 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 Beta-ketoadipyl-CoA thiolase P0C7L2 PAAJ_ECOLI paaJ http://ecmdb.ca/proteins/P0C7L2.xml 3-ketoacyl-CoA thiolase P21151 FADA_ECOLI fadA http://ecmdb.ca/proteins/P21151.xml Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml Probable 3-hydroxybutyryl-CoA dehydrogenase P76083 PAAH_ECOLI paaH http://ecmdb.ca/proteins/P76083.xml 3-ketoacyl-CoA thiolase_ P76503 FADI_ECOLI fadI http://ecmdb.ca/proteins/P76503.xml Fatty acid oxidation complex subunit alpha_ P77399 FADJ_ECOLI fadJ http://ecmdb.ca/proteins/P77399.xml Fatty acid oxidation complex subunit alpha P21177 FADB_ECOLI fadB http://ecmdb.ca/proteins/P21177.xml (3S)-3-Hydroxyadipyl-CoA + NAD <> Hydrogen ion + NADH + 3-Oxoadipyl-CoA R06941 Coenzyme A + 3-Oxoadipyl-CoA <> Acetyl-CoA + Succinyl-CoA R00829 RXN-3641 Succinyl-CoA + Acetyl-CoA <> Coenzyme A + 3-Oxoadipyl-CoA R00829 Succinyl-CoA + Acetyl-CoA < 3-Oxoadipyl-CoA + Coenzyme A RXN-3641 3-Hydroxyadipyl-CoA + NAD <> Hydrogen ion + 3-Oxoadipyl-CoA + NADH RXN0-2044 Succinyl-CoA + Acetyl-CoA > CoA + 3-Oxoadipyl-CoA