2.0 2012-10-10 12:14:08 -0600 2015-08-05 16:22:03 -0600 ECMDB23051 M2MDB003441 (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate Tricarboxylate anion of (2S,3R)-3-hydroxybutane-1,2,3-tricarboxylic acid (2S,3S)-2-Hydroxybutane-1,2,3-tricarboxylic acid C7H10O7 206.1501 206.042652674 (1S,2S)-2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid (2S,3S)-2-methylcitric acid C[C@H](C(O)=O)[C@@](O)(CC(O)=O)C(O)=O InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t3-,7+/m1/s1 YNOXCRMFGMSKIJ-NFNCENRGSA-N logp -0.89 ALOGPS logs -0.07 ALOGPS solubility 1.75e+02 g/l ALOGPS logp -0.78 ChemAxon pka_strongest_acidic 3.18 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac (1S,2S)-2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid ChemAxon average_mass 206.1501 ChemAxon mono_mass 206.042652674 ChemAxon smiles C[C@H](C(O)=O)[C@@](O)(CC(O)=O)C(O)=O ChemAxon formula C7H10O7 ChemAxon inchi InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t3-,7+/m1/s1 ChemAxon inchikey YNOXCRMFGMSKIJ-NFNCENRGSA-N ChemAxon polar_surface_area 132.13 ChemAxon refractivity 40.2 ChemAxon polarizability 17.33 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 4 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 Specdb::CMs 3420 Specdb::NmrOneD 320171 Specdb::NmrOneD 320172 Specdb::NmrOneD 320173 Specdb::NmrOneD 320174 Specdb::NmrOneD 320175 Specdb::NmrOneD 320176 Specdb::NmrOneD 320177 Specdb::NmrOneD 320178 Specdb::NmrOneD 320179 Specdb::NmrOneD 320180 Specdb::NmrOneD 320181 Specdb::NmrOneD 320182 Specdb::NmrOneD 320183 Specdb::NmrOneD 320184 Specdb::NmrOneD 320185 Specdb::NmrOneD 320186 Specdb::NmrOneD 320187 Specdb::NmrOneD 320188 Specdb::NmrOneD 320189 Specdb::NmrOneD 320190 Specdb::MsMs 25847 Specdb::MsMs 25848 Specdb::MsMs 25849 Specdb::MsMs 32405 Specdb::MsMs 32406 Specdb::MsMs 32407 2-methylcitrate dehydratase P77243 PRPD_ECOLI prpD http://ecmdb.ca/proteins/P77243.xml (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate > Cis-2-Methylaconitate + Water Water + Oxalacetic acid + Propionyl-CoA <> Methylcitric acid + Coenzyme A + Hydrogen ion + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate R00931 2-METHYLCITRATE-SYNTHASE-RXN Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water R04424 2-METHYLCITRATE-DEHYDRATASE-RXN Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water Water + Oxalacetic acid + Propionyl-CoA <> Methylcitric acid + Coenzyme A + Hydrogen ion + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water