2.0 2012-05-31 13:56:34 -0600 2015-10-15 16:13:59 -0600 ECMDB02310 M2MDB000456 (S)-Methylmalonyl-CoA Methylmalonyl-CoA is an intermediate in the metabolism of Propanoate. (2S)-methyl-malonyl-CoA (R)-methylmalonyl-CoA (R)-methylmalonyl-Coenzyme A (S)-2-Methyl-3-Oxopropanoyl-Coa (S)-methyl-malonyl-CoA (S)-methyl-malonyl-Coenzyme A CH3-malonyl-CoA CH3-malonyl-Coenzyme A D-Methylmalonyl-CoA D-Methylmalonyl-Coenzyme A L-Methylmalonyl-CoA L-Methylmalonyl-Coenzyme A Methyl-malonyl-coenzyme A C25H40N7O19P3S 867.607 867.131252359 (2S)-3-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-methyl-3-oxopropanoic acid (2S)-3-({2-[(3-{[(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-methyl-3-oxopropanoic acid 104809-02-1 C[C@@H](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 InChI=1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12-,13?,16+,17+,18-,22?/m0/s1 MZFOKIKEPGUZEN-JDVCRUKVSA-N Solid Cytosol logp -0.40 ALOGPS logs -2.20 ALOGPS solubility 5.49e+00 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.82 ChemAxon iupac (2S)-3-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-methyl-3-oxopropanoic acid ChemAxon average_mass 867.607 ChemAxon mono_mass 867.131252359 ChemAxon smiles C[C@@H](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 ChemAxon formula C25H40N7O19P3S ChemAxon inchi InChI=1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12-,13?,16+,17+,18-,22?/m0/s1 ChemAxon inchikey MZFOKIKEPGUZEN-JDVCRUKVSA-N ChemAxon polar_surface_area 407.91 ChemAxon refractivity 184.17 ChemAxon polarizability 75.96 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 21 ChemAxon donor_count 10 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Glyoxylate and dicarboxylate metabolism ec00630 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 Valine, leucine and isoleucine degradation ec00280 Microbial metabolism in diverse environments ec01120 methylmalonyl pathway PROPIONMET-PWY Specdb::MsMs 23999 Specdb::MsMs 24000 Specdb::MsMs 24001 Specdb::MsMs 30797 Specdb::MsMs 30798 Specdb::MsMs 30799 HMDB01269 613 388424 C00683 15466 D-METHYL-MALONYL-COA Methylmalonyl-CoA 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 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 http://hmdb.ca/system/metabolites/msds/000/001/137/original/HMDB01269.pdf?1358461607 Protein sbm P27253 SBM_ECOLI sbm http://ecmdb.ca/proteins/P27253.xml Methylmalonyl-CoA decarboxylase P52045 MMCD_ECOLI mmcD http://ecmdb.ca/proteins/P52045.xml Succinyl-CoA > (S)-Methylmalonyl-CoA Hydrogen ion + (S)-Methylmalonyl-CoA <> Carbon dioxide + Propionyl-CoA R00923 (S)-Methylmalonyl-CoA <> Propionyl-CoA + Carbon dioxide R00923 R-Methylmalonyl-CoA <> (S)-Methylmalonyl-CoA METHYLMALONYL-COA-EPIM-RXN Adenosine triphosphate + Hydrogen carbonate + Propionyl-CoA > Hydrogen ion + ADP + Phosphate + (S)-Methylmalonyl-CoA PROPIONYL-COA-CARBOXY-RXN (S)-Methylmalonyl-CoA > Propionyl-CoA + Carbon dioxide