2.0 2012-05-31 14:24:50 -0600 2015-06-03 17:19:12 -0600 ECMDB20050 M2MDB000899 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate 2-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 acid 5-Enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate 5-Enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylic acid Sephchc C14H16O9 328.2714 328.07943211 (1R,2S,5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acid sephchc [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)=O InChI=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/s1 XYCATPIYKOARSZ-OAIFWDMCSA-N Cytosol logp 0.24 ALOGPS logs -1.86 ALOGPS solubility 4.52e+00 g/l ALOGPS logp -0.6 ChemAxon pka_strongest_acidic 3.19 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (1R,2S,5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acid ChemAxon average_mass 328.2714 ChemAxon mono_mass 328.07943211 ChemAxon smiles [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)=O ChemAxon formula C14H16O9 ChemAxon inchi InChI=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/s1 ChemAxon inchikey XYCATPIYKOARSZ-OAIFWDMCSA-N ChemAxon polar_surface_area 158.43 ChemAxon refractivity 74.12 ChemAxon polarizability 29.9 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 9 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Ubiquinone and other terpenoid-quinone biosynthesis ec00130 Metabolic pathways eco01100 Menaquinol biosythesis Menaquinol 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. PW001897 Metabolic 1,4-dihydroxy-2-naphthoate biosynthesis I PWY-5837 Specdb::CMs 1084541 Specdb::NmrOneD 258308 Specdb::NmrOneD 258309 Specdb::NmrOneD 258310 Specdb::NmrOneD 258311 Specdb::NmrOneD 258312 Specdb::NmrOneD 258313 Specdb::NmrOneD 258314 Specdb::NmrOneD 258315 Specdb::NmrOneD 258316 Specdb::NmrOneD 258317 Specdb::NmrOneD 258318 Specdb::NmrOneD 258319 Specdb::NmrOneD 258320 Specdb::NmrOneD 258321 Specdb::NmrOneD 258322 Specdb::NmrOneD 258323 Specdb::NmrOneD 258324 Specdb::NmrOneD 258325 Specdb::NmrOneD 258326 Specdb::NmrOneD 258327 Specdb::MsMs 28880 Specdb::MsMs 28881 Specdb::MsMs 28882 Specdb::MsMs 35438 Specdb::MsMs 35439 Specdb::MsMs 35440 24883454 21865723 C16519 CPD-9924 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 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase P17109 MEND_ECOLI menD http://ecmdb.ca/proteins/P17109.xml 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase P37355 MENH_ECOLI menH http://ecmdb.ca/proteins/P37355.xml 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate <> (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid R08166 RXN-9310 alpha-Ketoglutarate + Hydrogen ion + Isochorismate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide R08165 Isochorismate + alpha-Ketoglutarate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide R08165 Hydrogen ion + Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide 2.5.1.64-RXN 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate > (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid R08166 RXN-9310 Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide isochorismate + Oxoglutaric acid + Hydrogen ion + Isochorismate > Carbon dioxide + 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate PW_R005214 2-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-carboxylate PW_R005216