2.0 2012-05-31 13:56:17 -0600 2015-10-15 16:13:58 -0600 ECMDB02255 M2MDB000451 R-Methylmalonyl-CoA R-methylmalonyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. Methylmalonyl-CoA is the coenzyme A linked form of methylmalonic acid. Methylmalonyl-CoA is formed from propionyl-CoA by propionyl-CoA carboxylase by help of biotin (vitamin B7). It is converted into succinyl-CoA by methylmalonyl-CoA mutase, in a reaction that requires vitamin B12 as a cofactor. In this way, it enters the Krebs cycle, and is thus part of one of the anaplerotic reactions. The following diagram demonstrates the aforementioned reactions: Propionyl CoA > Methylmalonyl CoA > Succinyl CoA (WikiPedia) CH3-malonyl-CoA L-Methylmalonyl-CoA Methyl-malonyl-coenzyme A Methylmalonyl-CoA C25H40N7O19P3S 867.607 867.131252359 (2R)-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 (2R)-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 73173-92-9 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(O)C1OP(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?/m1/s1 MZFOKIKEPGUZEN-YLYUOEEYSA-N Cytoplasm Periplasm 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 (2R)-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(O)C1OP(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?/m1/s1 ChemAxon inchikey MZFOKIKEPGUZEN-YLYUOEEYSA-N ChemAxon polar_surface_area 407.91 ChemAxon refractivity 184.17 ChemAxon polarizability 76.01 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 21 ChemAxon donor_count 10 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon conversion of succinate to propionate PWY0-43 methylmalonyl pathway PROPIONMET-PWY Specdb::EiMs 2987 Specdb::NmrOneD 279738 Specdb::NmrOneD 279739 Specdb::NmrOneD 279740 Specdb::NmrOneD 279741 Specdb::NmrOneD 279742 Specdb::NmrOneD 279743 Specdb::NmrOneD 279744 Specdb::NmrOneD 279745 Specdb::NmrOneD 279746 Specdb::NmrOneD 279747 Specdb::NmrOneD 279748 Specdb::NmrOneD 279749 Specdb::NmrOneD 279750 Specdb::NmrOneD 279751 Specdb::NmrOneD 279752 Specdb::NmrOneD 279753 Specdb::NmrOneD 279754 Specdb::NmrOneD 279755 Specdb::NmrOneD 279756 Specdb::NmrOneD 279757 Specdb::MsMs 25190 Specdb::MsMs 25191 Specdb::MsMs 25192 Specdb::MsMs 31748 Specdb::MsMs 31749 Specdb::MsMs 31750 HMDB02255 17216177 METHYL-MALONYL-COA MCA 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 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 Protein sbm P27253 SBM_ECOLI sbm http://ecmdb.ca/proteins/P27253.xml R-Methylmalonyl-CoA <> (S)-Methylmalonyl-CoA METHYLMALONYL-COA-EPIM-RXN R-Methylmalonyl-CoA <> Succinyl-CoA METHYLMALONYL-COA-MUT-RXN Hydrogen ion + R-Methylmalonyl-CoA > Propionyl-CoA + Carbon dioxide RXN0-310 R-Methylmalonyl-CoA > Succinyl-CoA METHYLMALONYL-COA-MUT-RXN