2.02012-05-31 14:27:32 -06002015-06-03 17:19:19 -0600ECMDB20101M2MDB0009495-Carboxy-2-pentenoyl-CoA5-carboxy-2-pentenoyl-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. Trans-2,3-Didehydroadipoyl-CoATrans-3,4-Dehydroadipyl-CoAC27H42N7O19P3S893.644893.146902423(4E)-6-({2-[(3-{[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)-6-oxohex-4-enoic acid5-carboxy-2-pentenoyl-coa138149-18-5[H]\C(CCC(=O)O)=C(\[H])C(=O)SCCN=C(O)CCN=C(O)C(O)([H])C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@@](O)([H])[C@]1([H])OP(O)(O)=OInChI=1S/C27H42N7O19P3S/c1-27(2,22(40)25(41)30-8-7-16(35)29-9-10-57-18(38)6-4-3-5-17(36)37)12-50-56(47,48)53-55(45,46)49-11-15-21(52-54(42,43)44)20(39)26(51-15)34-14-33-19-23(28)31-13-32-24(19)34/h4,6,13-15,20-22,26,39-40H,3,5,7-12H2,1-2H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/b6-4+/t15-,20-,21-,22?,26-/m1/s1ZFXICKRXPZTFPB-UWIQVNQSSA-NSolidCytosollogp-0.14logs-2.25solubility4.97e+00 g/llogp-3.3pka_strongest_acidic0.82pka_strongest_basic4.85iupac(4E)-6-({2-[(3-{[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)-6-oxohex-4-enoic acidaverage_mass893.644mono_mass893.146902423smiles[H]\C(CCC(=O)O)=C(\[H])C(=O)SCCN=C(O)CCN=C(O)C(O)([H])C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@@](O)([H])[C@]1([H])OP(O)(O)=OformulaC27H42N7O19P3SinchiInChI=1S/C27H42N7O19P3S/c1-27(2,22(40)25(41)30-8-7-16(35)29-9-10-57-18(38)6-4-3-5-17(36)37)12-50-56(47,48)53-55(45,46)49-11-15-21(52-54(42,43)44)20(39)26(51-15)34-14-33-19-23(28)31-13-32-24(19)34/h4,6,13-15,20-22,26,39-40H,3,5,7-12H2,1-2H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/b6-4+/t15-,20-,21-,22?,26-/m1/s1inchikeyZFXICKRXPZTFPB-UWIQVNQSSA-Npolar_surface_area407.91refractivity194.44polarizability80.01rotatable_bond_count24acceptor_count21donor_count10physiological_charge-4formal_charge0Phenylalanine metabolismThe 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.PW000921ec00360MetabolicCaprolactam degradationec00930Microbial metabolism in diverse environmentsec01120Specdb::EiMs5215Specdb::NmrOneD250008Specdb::NmrOneD250009Specdb::NmrOneD250010Specdb::NmrOneD250011Specdb::NmrOneD250012Specdb::NmrOneD250013Specdb::NmrOneD250014Specdb::NmrOneD250015Specdb::NmrOneD250016Specdb::NmrOneD250017Specdb::NmrOneD250018Specdb::NmrOneD250019Specdb::NmrOneD250020Specdb::NmrOneD250021Specdb::NmrOneD250022Specdb::NmrOneD250023Specdb::NmrOneD250024Specdb::NmrOneD250025Specdb::NmrOneD250026Specdb::NmrOneD250027Specdb::MsMs27935Specdb::MsMs27936Specdb::MsMs27937Specdb::MsMs34493Specdb::MsMs34494Specdb::MsMs34495247987114445509C14144Kanehisa, 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-D114.22080510Beta-ketoadipyl-CoA thiolaseP0C7L2PAAJ_ECOLIpaaJhttp://ecmdb.ca/proteins/P0C7L2.xmlFatty acid oxidation complex subunit alphaP21177FADB_ECOLIfadBhttp://ecmdb.ca/proteins/P21177.xmlProbable enoyl-CoA hydratase paaFP76082PAAF_ECOLIpaaFhttp://ecmdb.ca/proteins/P76082.xmlFatty acid oxidation complex subunit alpha_P77399FADJ_ECOLIfadJhttp://ecmdb.ca/proteins/P77399.xmlProbable enoyl-CoA hydratase paaGP77467PAAG_ECOLIpaaGhttp://ecmdb.ca/proteins/P77467.xmlFatty acid oxidation complex subunit alphaP21177FADB_ECOLIfadBhttp://ecmdb.ca/proteins/P21177.xml3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A <> 5-Carboxy-2-pentenoyl-CoA + Acetyl-CoAR098395-Carboxy-2-pentenoyl-CoA + Water <> (3S)-3-Hydroxyadipyl-CoAR06942Water + 5-Carboxy-2-pentenoyl-CoA > (3S)-3-Hydroxyadipyl-CoAPW_R0025103 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A <>5 5-Carboxy-2-pentenoyl-CoA + Acetyl-CoA3 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A <>5 5-Carboxy-2-pentenoyl-CoA + Acetyl-CoA