2.0 2012-05-31 13:02:31 -0600 2015-09-13 15:15:20 -0600 ECMDB00958 M2MDB000208 trans-Aconitic acid Trans-aconitic acid 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). The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerization of citrate to isocitrate in the citric acid cycle. It is acted upon by the enzyme aconitase. Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid. (WikiPedia) (1E)-1-Propene-1,2,3-tricarboxylate (1E)-1-propene-1,2,3-tricarboxylic acid (1E)-Prop-1-ene-1,2,3-tricarboxylic (1E)1-Propene-1,2,3-tricarboxylate (1E)1-Propene-1,2,3-tricarboxylic acid (<i>E</i>)-prop-1-ene-1,2,3-tricarboxylate (e)-1-Propene-1,2,3-tricarboxylate (E)-1-propene-1,2,3-tricarboxylic acid (e)-Aconitate (E)-Aconitic acid (E)-prop-1-ene-1,2,3-tricarboxylate (E)-prop-1-ene-1,2,3-tricarboxylic acid 1-Propene-1-trans-2,3-tricarboxylate 1-Propene-1-trans-2,3-tricarboxylic acid 1-trans-Propene-1,2,3-tricarboxylate 1-trans-Propene-1,2,3-tricarboxylic acid <i>trans</i>-aconitic acid Acid TRA trans-1-Propene-1,2,3-tricarboxylate Trans-1-Propene-1,2,3-tricarboxylic acid Trans-Aconitate Trans-Aconitic acid trans-Propene-1,2,3-tricarboxylate Trans-Propene-1,2,3-tricarboxylic acid C6H6O6 174.1082 174.016437924 (1E)-prop-1-ene-1,2,3-tricarboxylic acid trans aconitic acid 4023-65-8 OC(=O)C\C(=C/C(O)=O)C(O)=O InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+ GTZCVFVGUGFEME-HNQUOIGGSA-N Solid Cytosol logp -0.41 ALOGPS logs -1.41 ALOGPS solubility 6.72e+00 g/l ALOGPS melting_point 187 - 191 oC logp -0.52 ChemAxon pka_strongest_acidic 3.15 ChemAxon iupac (1E)-prop-1-ene-1,2,3-tricarboxylic acid ChemAxon average_mass 174.1082 ChemAxon mono_mass 174.016437924 ChemAxon smiles OC(=O)C\C(=C/C(O)=O)C(O)=O ChemAxon formula C6H6O6 ChemAxon inchi InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+ ChemAxon inchikey GTZCVFVGUGFEME-HNQUOIGGSA-N ChemAxon polar_surface_area 111.9 ChemAxon refractivity 35.23 ChemAxon polarizability 13.96 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Secondary Metabolites: Glyoxylate cycle The glyoxylate cycle starts with the interaction of Acetyl-Coa with a water molecule and Oxalacetic acid interact through a Citrate synthase resulting in a release of a coenzyme a and citric acid. The citric acid gets dehydrated through a citrate hydro-lyase resulting in the release of a water molecule and cis-Aconitic acid. The cis-Aconitic acid is then hydrated in an reversible reaction through an aconitate hydratase resulting in an Isocitric acid. The isocitric acid then interacts in a reversible reaction through isocitrate lyase resulting in the release of a succinic acid and a glyoxylic acid. The glyoxylic acid then reacts in a reversible reaction with an acetyl-coa, and a water molecule in a reversible reaction, resulting in a release of a coenzyme A, a hydrogen ion and an L-malic acid. The L-malic acid interacts in a reversible reaction through a NAD driven malate dehydrogenase resulting in the release of NADH, a hydrogen ion and an Oxalacetic acid. PW000967 Metabolic Specdb::CMs 1419 Specdb::CMs 2632 Specdb::CMs 31269 Specdb::CMs 32350 Specdb::CMs 37865 Specdb::CMs 152674 Specdb::EiMs 1898 Specdb::NmrOneD 1623 Specdb::NmrOneD 8082 Specdb::NmrOneD 8083 Specdb::NmrOneD 8084 Specdb::NmrOneD 8085 Specdb::NmrOneD 8086 Specdb::NmrOneD 8087 Specdb::NmrOneD 8088 Specdb::NmrOneD 8089 Specdb::NmrOneD 8090 Specdb::NmrOneD 8091 Specdb::NmrOneD 8092 Specdb::NmrOneD 8093 Specdb::NmrOneD 8094 Specdb::NmrOneD 8095 Specdb::NmrOneD 8096 Specdb::NmrOneD 8097 Specdb::NmrOneD 8098 Specdb::NmrOneD 8099 Specdb::NmrOneD 8100 Specdb::NmrOneD 8101 Specdb::MsMs 1360 Specdb::MsMs 1361 Specdb::MsMs 1362 Specdb::MsMs 4975 Specdb::MsMs 4976 Specdb::MsMs 4977 Specdb::MsMs 4978 Specdb::MsMs 4979 Specdb::MsMs 4980 Specdb::MsMs 178581 Specdb::MsMs 178582 Specdb::MsMs 178583 Specdb::MsMs 180900 Specdb::MsMs 180901 Specdb::MsMs 180902 Specdb::MsMs 437211 Specdb::MsMs 437212 Specdb::MsMs 437213 Specdb::MsMs 437214 Specdb::MsMs 437215 Specdb::MsMs 439246 Specdb::MsMs 2227012 Specdb::MsMs 2227720 Specdb::MsMs 2229413 Specdb::MsMs 2230044 Specdb::NmrTwoD 1564 HMDB00958 392201 C02341 15708 CPD-225 TRA 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 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Tanaka K, Hine DG: Compilation of gas chromatographic retention indices of 163 metabolically important organic acids, and their use in detection of patients with organic acidurias. J Chromatogr. 1982 Apr 30;239:301-22. 7096501 Tsai MY, Oliphant C, Josephson MW: Identification of metabolites diagnostic for organic acidurias by simultaneous dual-column capillary gas chromatography. J Chromatogr. 1985 May 31;341(1):1-10. 4019674 Koide K, Toyama J, Inoue N, Koshikawa S, Akizawa T, Takahashi K, Hidaka S, Yamane Y, Shinoda K, Nakao M, et al.: [Uremic peak 2a in high performance liquid chromatography--acidic components and their membrane permeability]. Nihon Jinzo Gakkai Shi. 1986 Nov;28(11):1481-9. 2950263 Gutierrez, Eddie N.; Lamberti, Vincent. Preparation of aconitic acid. U.S. (1978), 5 pp. CODEN: USXXAM US 4123459 19781031 CAN 90:103423 AN 1979:103423 http://hmdb.ca/system/metabolites/msds/000/000/862/original/HMDB00958.pdf?1358896083 Trans-aconitate 2-methyltransferase P76145 TAM_ECOLI tam http://ecmdb.ca/proteins/P76145.xml trans-Aconitic acid + S-Adenosylmethionine > E-3-Carboxy-2-pentenedioate 6-methyl ester + S-Adenosylhomocysteine RXN0-2441 trans-Aconitic acid <> cis-Aconitic acid ACONITATE-DELTA-ISOMERASE-RXN trans-Aconitic acid cis-Aconitic acid ACONITATE-DELTA-ISOMERASE-RXN S-adenosyl-L-methionine + trans-Aconitic acid > S-Adenosylhomocysteine + (E)-3-(Methoxycarbonyl)pent-2-enedioate S-Adenosylmethionine + trans-Aconitic acid <> S-Adenosylhomocysteine + E-3-Carboxy-2-pentenedioate 6-methyl ester R05763 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 95.9 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 383600 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 72.3 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 289200 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621