2.0 2015-09-08 17:48:53 -0600 2015-09-08 17:48:53 -0600 ECMDB24063 M2MDB006180 Methylmalonyl-CoA C25H40N7O19P3S 867.607 867.131252359 (2S)-3-{[2-(3-{3-[({[({[(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)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-methyl-3-oxopropanoic acid (2S)-3-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-2-methyl-3-oxopropanoic acid C[C@@H](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N 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-PNEPRAIJSA-N logp -0.60 ALOGPS logs -2.39 ALOGPS solubility 3.57e+00 g/l ALOGPS logp -6.5 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.97 ChemAxon iupac (2S)-3-{[2-(3-{3-[({[({[(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)methyl]-2-hydroxy-3-methylbutanamido}propanamido)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(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N 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-PNEPRAIJSA-N ChemAxon polar_surface_area 400.93 ChemAxon refractivity 183.13 ChemAxon polarizability 75.35 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 19 ChemAxon donor_count 10 ChemAxon physiological_charge -5 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 threonine biosynthesis The biosynthesis of threonine starts with oxalacetic acid interacting with an L-glutamic acid through an aspartate aminotransferase resulting in a oxoglutaric acid and an L-aspartic acid. The latter compound is then phosphorylated by an ATP driven Aspartate kinase resulting in an a release of an ADP and an L-aspartyl-4-phosphate. This compound interacts with a hydrogen ion through an NADPH driven aspartate semialdehyde dehydrogenase resulting in the release of a phosphate, an NADP and a L-aspartate-semialdehyde.The latter compound interacts with a hydrogen ion through a NADPH driven aspartate kinase / homoserine dehydrogenase resulting in the release of an NADP and a L-homoserine. L-homoserine is phosphorylated through an ATP driven homoserine kinase resulting in the release of an ADP, a hydrogen ion and a O-phosphohomoserine. The latter compound then interacts with a water molecule threonine synthase resulting in the release of a phosphate and an L-threonine. PW000817 Metabolic Specdb::NmrOneD 147070 Specdb::NmrOneD 147071 Specdb::NmrOneD 147072 Specdb::NmrOneD 147073 Specdb::NmrOneD 147074 Specdb::NmrOneD 147075 Specdb::NmrOneD 147076 Specdb::NmrOneD 147077 Specdb::NmrOneD 147078 Specdb::NmrOneD 147079 Specdb::NmrOneD 147080 Specdb::NmrOneD 147081 Specdb::NmrOneD 147082 Specdb::NmrOneD 147083 Specdb::NmrOneD 147084 Specdb::NmrOneD 147085 Specdb::NmrOneD 147086 Specdb::NmrOneD 147087 Specdb::NmrOneD 147088 Specdb::NmrOneD 147089 Specdb::MsMs 29270 Specdb::MsMs 29271 Specdb::MsMs 29272 Specdb::MsMs 35828 Specdb::MsMs 35829 Specdb::MsMs 35830 Specdb::MsMs 2268607 Specdb::MsMs 2268608 Specdb::MsMs 2268609 Specdb::MsMs 3070971 Specdb::MsMs 3070972 Specdb::MsMs 3070973 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 + Succinyl-CoA > Methylmalonyl-CoA PW_R003502 Methylmalonyl-CoA + Hydrogen ion > Carbon dioxide + Propionyl-CoA + Propionyl-CoA PW_R003503