2.0 2012-05-31 14:08:14 -0600 2015-06-03 15:54:51 -0600 ECMDB06357 M2MDB000668 Cis-2-Methylaconitate cis-2-Methylaconitate is produced due to the dehydration of 2-methylcitrate in 2-methylcitric acid cycle. The cycle is catalyzed by a cofactor-less (PrpD) enzyme or by an aconitase-like (AcnD) enzyme. (PMID: 17567742) (2Z)-but-2-ene-1,2,3-tricarboxylate (2Z)-but-2-ene-1,2,3-tricarboxylic acid (Z)-2-Butene-1,2,3-tricarboxylate (Z)-2-Butene-1,2,3-tricarboxylic acid (Z)-But-2-ene-1,2,3-tricarboxylate (Z)-But-2-ene-1,2,3-tricarboxylic acid 2-methyl-<I>cis</I>-aconitate 2-Methyl-cis-aconitate 2-Methyl-cis-aconitic acid 2-methylaconitate 2-Methylaconitic acid a-Methyl-cis-aconitate a-Methyl-cis-aconitic acid a-Methylaconitate a-Methylaconitic acid Alpha-Methyl-cis-aconitate Alpha-Methyl-cis-aconitic acid Alpha-Methylaconitate Alpha-Methylaconitic acid Cis-2-Butene-1,2,3-tricarboxylate Cis-2-Butene-1,2,3-tricarboxylic acid Cis-2-Methylaconitic acid α-Methyl-cis-aconitate α-Methyl-cis-aconitic acid α-Methylaconitate α-Methylaconitic acid C7H8O6 188.1348 188.032087988 (1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid α-methylaconitate 6061-93-4 C\C(C(O)=O)=C(/CC(O)=O)C(O)=O InChI=1S/C7H8O6/c1-3(6(10)11)4(7(12)13)2-5(8)9/h2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/b4-3- NUZLRKBHOBPTQV-ARJAWSKDSA-N Solid Cytosol logp -0.33 ALOGPS logs -1.77 ALOGPS solubility 3.16e+00 g/l ALOGPS logp -0.13 ChemAxon pka_strongest_acidic 2.25 ChemAxon iupac (1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid ChemAxon average_mass 188.1348 ChemAxon mono_mass 188.032087988 ChemAxon smiles C\C(C(O)=O)=C(/CC(O)=O)C(O)=O ChemAxon formula C7H8O6 ChemAxon inchi InChI=1S/C7H8O6/c1-3(6(10)11)4(7(12)13)2-5(8)9/h2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/b4-3- ChemAxon inchikey NUZLRKBHOBPTQV-ARJAWSKDSA-N ChemAxon polar_surface_area 111.9 ChemAxon refractivity 39.59 ChemAxon polarizability 15.55 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Propanoate metabolism Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA. Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate. Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid. Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA. ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid. Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA. PW000940 ec00640 Metabolic 2-methylcitrate cycle I PWY0-42 Specdb::CMs 3118 Specdb::CMs 39009 Specdb::CMs 166594 Specdb::NmrOneD 74272 Specdb::NmrOneD 74273 Specdb::NmrOneD 74274 Specdb::NmrOneD 74275 Specdb::NmrOneD 74276 Specdb::NmrOneD 74277 Specdb::NmrOneD 74278 Specdb::NmrOneD 74279 Specdb::NmrOneD 74280 Specdb::NmrOneD 74281 Specdb::NmrOneD 74282 Specdb::NmrOneD 74283 Specdb::NmrOneD 74284 Specdb::NmrOneD 74285 Specdb::NmrOneD 74286 Specdb::NmrOneD 74287 Specdb::NmrOneD 74288 Specdb::NmrOneD 74289 Specdb::NmrOneD 74290 Specdb::NmrOneD 74291 Specdb::MsMs 24551 Specdb::MsMs 24552 Specdb::MsMs 24553 Specdb::MsMs 31109 Specdb::MsMs 31110 Specdb::MsMs 31111 Specdb::MsMs 2706098 Specdb::MsMs 2706099 Specdb::MsMs 2706100 Specdb::MsMs 2999188 Specdb::MsMs 2999189 Specdb::MsMs 2999190 HMDB06357 3080625 2338376 C04225 16717 CPD-1136 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 Garvey, G. S., Rocco, C. J., Escalante-Semerena, J. C., Rayment, I. (2007). "The three-dimensional crystal structure of the PrpF protein of Shewanella oneidensis complexed with trans-aconitate: insights into its biological function." Protein Sci 16:1274-1284. 17567742 Tabuchi, Takeshi; Uchiyama, Hiroo. Methylcitrate condensing and methylisocitrate cleaving enzymes. Evidence for the pathway of oxidation of propionyl-CoA to pyruvate via C7-tricarboxylic acids. Agricultural and Biological Chemistry (1975), 39(10), Aconitate hydratase 2 P36683 ACON2_ECOLI acnB http://ecmdb.ca/proteins/P36683.xml 2-methylcitrate dehydratase P77243 PRPD_ECOLI prpD http://ecmdb.ca/proteins/P77243.xml Cis-2-Methylaconitate + Water <> Methylisocitric acid R04425 4.2.1.99-RXN Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water R04424 2-METHYLCITRATE-DEHYDRATASE-RXN Methylcitric acid <> Cis-2-Methylaconitate + Water R04424 Methylisocitric acid <> Cis-2-Methylaconitate + Water R04425 Methylcitric acid > Water + Cis-2-Methylaconitate R04424 2-METHYLCITRATE-DEHYDRATASE-RXN (2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate > Cis-2-Methylaconitate + Water (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate > Cis-2-Methylaconitate + Water 2-Methylcitric acid + Methylcitric acid > Water + Cis-2-Methylaconitate PW_R003498 Cis-2-Methylaconitate > Water + Methylisocitric acid PW_R003499 Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water