2.0 2012-07-30 14:54:45 -0600 2015-06-03 17:20:48 -0600 ECMDB21172 M2MDB001581 3-Oxo-5,6-dehydrosuberyl-CoA 3-Oxo-5,6-dehydrosuberyl-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. (5<i>Z</i>)-7-carboxy-3-oxohept-5-enoyl-CoA (5Z)-7-carboxy-3-oxohept-5-enoyl-CoA C29H44N7O20P3S 935.681 935.157467109 8-({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)-6,8-dioxooct-3-enoic acid 8-({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)-6,8-dioxooct-3-enoic acid [H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CC(=O)CC=CCC(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O InChI=1S/C29H44N7O20P3S/c1-29(2,24(43)27(44)32-8-7-18(38)31-9-10-60-20(41)11-16(37)5-3-4-6-19(39)40)13-53-59(50,51)56-58(48,49)52-12-17-23(55-57(45,46)47)22(42)28(54-17)36-15-35-21-25(30)33-14-34-26(21)36/h3-4,14-15,17,22-24,28,42-43H,5-13H2,1-2H3,(H,31,38)(H,32,44)(H,39,40)(H,48,49)(H,50,51)(H2,30,33,34)(H2,45,46,47)/t17-,22-,23-,24+,28-/m1/s1 IFFFDKYRRUVOFP-NOQDIWQESA-N Cytosol logp 0.05 ALOGPS logs -2.23 ALOGPS solubility 5.46e+00 g/l ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.83 ChemAxon iupac 8-({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)-6,8-dioxooct-3-enoic acid ChemAxon average_mass 935.681 ChemAxon mono_mass 935.157467109 ChemAxon smiles [H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CC(=O)CC=CCC(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O ChemAxon formula C29H44N7O20P3S ChemAxon inchi InChI=1S/C29H44N7O20P3S/c1-29(2,24(43)27(44)32-8-7-18(38)31-9-10-60-20(41)11-16(37)5-3-4-6-19(39)40)13-53-59(50,51)56-58(48,49)52-12-17-23(55-57(45,46)47)22(42)28(54-17)36-15-35-21-25(30)33-14-34-26(21)36/h3-4,14-15,17,22-24,28,42-43H,5-13H2,1-2H3,(H,31,38)(H,32,44)(H,39,40)(H,48,49)(H,50,51)(H2,30,33,34)(H2,45,46,47)/t17-,22-,23-,24+,28-/m1/s1 ChemAxon inchikey IFFFDKYRRUVOFP-NOQDIWQESA-N ChemAxon polar_surface_area 424.98 ChemAxon refractivity 204.36 ChemAxon polarizability 83.17 ChemAxon rotatable_bond_count 26 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 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 5046 Specdb::NmrOneD 318141 Specdb::NmrOneD 318142 Specdb::NmrOneD 318143 Specdb::NmrOneD 318144 Specdb::NmrOneD 318145 Specdb::NmrOneD 318146 Specdb::NmrOneD 318147 Specdb::NmrOneD 318148 Specdb::NmrOneD 318149 Specdb::NmrOneD 318150 Specdb::NmrOneD 318151 Specdb::NmrOneD 318152 Specdb::NmrOneD 318153 Specdb::NmrOneD 318154 Specdb::NmrOneD 318155 Specdb::NmrOneD 318156 Specdb::NmrOneD 318157 Specdb::NmrOneD 318158 Specdb::NmrOneD 318159 Specdb::NmrOneD 318160 Specdb::MsMs 36902 Specdb::MsMs 36903 Specdb::MsMs 36904 Specdb::MsMs 39350 Specdb::MsMs 39351 Specdb::MsMs 39352 56927776 C19945 CPD0-2364 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 Beta-ketoadipyl-CoA thiolase P0C7L2 PAAJ_ECOLI paaJ http://ecmdb.ca/proteins/P0C7L2.xml Probable enoyl-CoA hydratase paaG P77467 PAAG_ECOLI paaG http://ecmdb.ca/proteins/P77467.xml Protein maoC P77455 MAOC_ECOLI maoC http://ecmdb.ca/proteins/P77455.xml 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A <> 5-Carboxy-2-pentenoyl-CoA + Acetyl-CoA R09839 2-Oxepin-2(3H)-ylideneacetyl-CoA + 2 Water + NADP > 3-Oxo-5,6-dehydrosuberyl-CoA +2 Hydrogen ion + NADPH RXN0-6511 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP + Water <> 3-Oxo-5,6-dehydrosuberyl-CoA + NADPH + Hydrogen ion R09820 2-Oxepin-2(3H)-ylideneacetyl-CoA + NADP + Water > 3-Oxo-5,6-dehydrosuberyl-CoA + NADPH + Hydrogen ion RXN0-6511 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A > 2,3-dehydroadipyl-CoA + Acetyl-CoA RXN0-6512 3-oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP + Water > 3-Oxo-5,6-dehydrosuberyl-CoA + NADPH + Hydrogen ion RXNMETA-12672 2,3-dehydroadipyl-CoA + Acetyl-CoA > CoA + 3-Oxo-5,6-dehydrosuberyl-CoA 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP + Water > 3-Oxo-5,6-dehydrosuberyl-CoA + NADPH 3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde + Water + NADP > Hydrogen ion + NADPH + 3-Oxo-5,6-dehydrosuberyl-CoA PW_R005922 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A > Acetyl-CoA + 2,3-didehydroadipyl-CoA PW_R005923 3 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A <>5 5-Carboxy-2-pentenoyl-CoA + Acetyl-CoA 3 3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A <>5 5-Carboxy-2-pentenoyl-CoA + Acetyl-CoA