2.02012-05-31 14:08:34 -06002015-06-03 15:54:52 -0600ECMDB06471M2MDB000674Methylisocitric acidMethylisocitric acid is a product of bacterial metabolism in the gut. It can be produced by 2-methylisocitrate lyase and by 2-methylisocitrate dehydratase.(2R,3S)2-methylisocitrate(2R,3S)2-methylisocitric acid(2S,3R)-3-Hydroxybutane-1,2,3-tricarboxylate(2S,3R)-3-Hydroxybutane-1,2,3-tricarboxylic acid3-Carboxy-2,3-dideoxy-4-C-methylpentarate3-Carboxy-2,3-dideoxy-4-C-methylpentaric acid3-Hydroxy-1,2,3-butanetricarboxylate3-Hydroxy-1,2,3-butanetricarboxylic acid3-Hydroxybutane-1,2,3-tricarboxylate3-Hydroxybutane-1,2,3-tricarboxylic acid<i>threo</i>-Ds-2-methylisocitratea-Methylisocitratea-Methylisocitric acidAlpha-MethylisocitrateAlpha-Methylisocitric acidD.L-MethylisocitrateD.L-Methylisocitric acidDL-MethylisocitrateDL-Methylisocitric acidDL-threo-a-MethylisocitrateDL-threo-a-Methylisocitric acidDL-threo-alpha-methylisocitrateDL-threo-alpha-methylisocitric acidDL-threo-α-MethylisocitrateDL-threo-α-Methylisocitric acidMethylisocitrateMethylisocitric acidthreo-a-Methylisocitratethreo-a-Methylisocitric acidThreo-alpha-methylisocitrateThreo-alpha-methylisocitric acidThreo-Ds-2-methylisocitrateThreo-Ds-2-methylisocitric acidthreo-α-Methylisocitratethreo-α-Methylisocitric acidα-Methylisocitrateα-Methylisocitric acidC7H10O7206.1501206.0426526741-hydroxy-1-methylpropane-1,2,3-tricarboxylic acidα-methylisocitric acidCC(O)(C(CC(O)=O)C(O)=O)C(O)=OInChI=1S/C7H10O7/c1-7(14,6(12)13)3(5(10)11)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)HHKPKXCSHMJWCF-UHFFFAOYSA-NSolidCytosollogp-0.87logs-0.14solubility1.49e+02 g/llogp-1pka_strongest_acidic3.17pka_strongest_basic-4.1iupac1-hydroxy-1-methylpropane-1,2,3-tricarboxylic acidaverage_mass206.1501mono_mass206.042652674smilesCC(O)(C(CC(O)=O)C(O)=O)C(O)=OformulaC7H10O7inchiInChI=1S/C7H10O7/c1-7(14,6(12)13)3(5(10)11)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)inchikeyHHKPKXCSHMJWCF-UHFFFAOYSA-Npolar_surface_area132.13refractivity40.43polarizability17.37rotatable_bond_count5acceptor_count7donor_count4physiological_charge-3formal_charge0Propanoate 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.PW000940ec00640Metabolic2-methylcitrate cycle IPWY0-42Specdb::CMs2431Specdb::CMs39021Specdb::CMs168257Specdb::NmrOneD10982Specdb::NmrOneD10983Specdb::NmrOneD10984Specdb::NmrOneD10985Specdb::NmrOneD10986Specdb::NmrOneD10987Specdb::NmrOneD10988Specdb::NmrOneD10989Specdb::NmrOneD10990Specdb::NmrOneD10991Specdb::NmrOneD10992Specdb::NmrOneD10993Specdb::NmrOneD10994Specdb::NmrOneD10995Specdb::NmrOneD10996Specdb::NmrOneD10997Specdb::NmrOneD10998Specdb::NmrOneD10999Specdb::NmrOneD11000Specdb::NmrOneD11001Specdb::MsMs25727Specdb::MsMs25728Specdb::MsMs25729Specdb::MsMs32285Specdb::MsMs32286Specdb::MsMs32287Specdb::MsMs2670585Specdb::MsMs2670586Specdb::MsMs2670587Specdb::MsMs3008605Specdb::MsMs3008606Specdb::MsMs3008607HMDB06471513498C0459315607CPD-618Keseler, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Aconitate hydratase 2P36683ACON2_ECOLIacnBhttp://ecmdb.ca/proteins/P36683.xmlMethylisocitrate lyaseP77541PRPB_ECOLIprpBhttp://ecmdb.ca/proteins/P77541.xmlCis-2-Methylaconitate + Water <> Methylisocitric acidR044254.2.1.99-RXNMethylisocitric acid <> Pyruvic acid + Succinic acidR00409METHYLISOCITRATE-LYASE-RXNMethylisocitric acid <> Cis-2-Methylaconitate + WaterR04425Methylisocitric acid > Succinic acid + Pyruvic acidMETHYLISOCITRATE-LYASE-RXNCis-2-Methylaconitate > Water + Methylisocitric acidPW_R003499Methylisocitric acid <> Pyruvic acid + Succinic acidMethylisocitric acid <> Pyruvic acid + Succinic acid