2.02012-05-31 14:24:50 -06002015-06-03 17:19:12 -0600ECMDB20050M2MDB0008992-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate is a member of the chemical class known as Tricarboxylic Acids and Derivatives. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof). 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic acid5-Enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate5-Enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylic acidSephchcC14H16O9328.2714328.07943211(1R,2S,5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acidsephchc[H][C@@]1(O)[C@@]([H])(OC(=C)C(O)=O)C=C[C@]([H])(C(=O)CCC(O)=O)[C@@]1([H])C(O)=OInChI=1S/C14H16O9/c1-6(13(19)20)23-9-4-2-7(8(15)3-5-10(16)17)11(12(9)18)14(21)22/h2,4,7,9,11-12,18H,1,3,5H2,(H,16,17)(H,19,20)(H,21,22)/t7-,9+,11-,12-/m1/s1XYCATPIYKOARSZ-OAIFWDMCSA-NCytosollogp0.24logs-1.86solubility4.52e+00 g/llogp-0.6pka_strongest_acidic3.19pka_strongest_basic-3.4iupac(1R,2S,5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acidaverage_mass328.2714mono_mass328.07943211smiles[H][C@@]1(O)[C@@]([H])(OC(=C)C(O)=O)C=C[C@]([H])(C(=O)CCC(O)=O)[C@@]1([H])C(O)=OformulaC14H16O9inchiInChI=1S/C14H16O9/c1-6(13(19)20)23-9-4-2-7(8(15)3-5-10(16)17)11(12(9)18)14(21)22/h2,4,7,9,11-12,18H,1,3,5H2,(H,16,17)(H,19,20)(H,21,22)/t7-,9+,11-,12-/m1/s1inchikeyXYCATPIYKOARSZ-OAIFWDMCSA-Npolar_surface_area158.43refractivity74.12polarizability29.9rotatable_bond_count8acceptor_count9donor_count4physiological_charge-3formal_charge0Ubiquinone and other terpenoid-quinone biosynthesisec00130Metabolic pathwayseco01100Menaquinol biosythesisMenaquinol biosynthesis starts with chorismate being metabolized into isochorismate through a isochorismate synthase. Isochorismate then interacts with 2-oxoglutare and a hydrogen ion through a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase resulting in the release of a carbon dioxide and a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate. The latter compound then interacts with (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase resulting in the release of a pyruvate and a (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate. This compound is the dehydrated through a o-succinylbenzoate synthase resulting in the release of a water molecule and a 2-succinylbenzoate. This compound then interacts with a coenzyme A and an ATP through a o-succinylbenzoate CoA ligase resulting in the release of a diphosphate, a AMP and a succinylbenzoyl-CoA. The latter compound interacts with a hydrogen ion through a 1,4-dihydroxy-2-naphthoyl-CoA synthase resulting in the release of a water molecule or a 1,4-dihydroxy-2-naphthoyl-CoA. This compound then interacts with water through a 1,4-dihydroxy-2-naphthoyl-CoA thioesterase resulting in the release of a coenzyme A, a hydrogen ion and a 1,4-dihydroxy-2-naphthoate.
The 1,4-dihydroxy-2-naphthoate can interact with either farnesylfarnesylgeranyl-PP or octaprenyl diphosphate and a hydrogen ion through a 1,4-dihydroxy-2-naphthoate octaprenyltransferase resulting in a release of a carbon dioxide, a pyrophosphate and a demethylmenaquinol-8. This compound then interacts with SAM through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a hydrogen ion, a s-adenosyl-L-homocysteine and a menaquinol.PW001897Metabolic1,4-dihydroxy-2-naphthoate biosynthesis IPWY-5837Specdb::CMs1084541Specdb::NmrOneD258308Specdb::NmrOneD258309Specdb::NmrOneD258310Specdb::NmrOneD258311Specdb::NmrOneD258312Specdb::NmrOneD258313Specdb::NmrOneD258314Specdb::NmrOneD258315Specdb::NmrOneD258316Specdb::NmrOneD258317Specdb::NmrOneD258318Specdb::NmrOneD258319Specdb::NmrOneD258320Specdb::NmrOneD258321Specdb::NmrOneD258322Specdb::NmrOneD258323Specdb::NmrOneD258324Specdb::NmrOneD258325Specdb::NmrOneD258326Specdb::NmrOneD258327Specdb::MsMs28880Specdb::MsMs28881Specdb::MsMs28882Specdb::MsMs35438Specdb::MsMs35439Specdb::MsMs354402488345421865723C16519CPD-9924Keseler, 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-D590.21097882Kanehisa, 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-D114.220805102-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthaseP17109MEND_ECOLImenDhttp://ecmdb.ca/proteins/P17109.xml2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthaseP37355MENH_ECOLImenHhttp://ecmdb.ca/proteins/P37355.xml2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate <> (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acidR08166RXN-9310alpha-Ketoglutarate + Hydrogen ion + Isochorismate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxideR08165Isochorismate + alpha-Ketoglutarate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxideR08165Hydrogen ion + Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide2.5.1.64-RXN2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate > (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acidR08166RXN-9310Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxideisochorismate + Oxoglutaric acid + Hydrogen ion + Isochorismate > Carbon dioxide + 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylatePW_R0052142-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate > (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid + (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylatePW_R005216