2.0 2012-05-31 13:48:58 -0600 2015-09-17 15:41:10 -0600 ECMDB01275 M2MDB000321 Propionyl-CoA Propionyl-CoA is an intermediate in the metabolism of propanoate. Propionyl-CoA is a substrate for acetyl-CoA synthetase, propionyl-CoA synthetase and 2-methylcitrate synthase. It is also involved in beta-alanine metabolism, Valine, leucine abd isoleucine degradation and C5-branched dibasic acid metabolism pathways. 2-methylacetyl-CoA 2-methylacetyl-Coenzyme A a-Methylacetyl-CoA a-Methylacetyl-coenzyme A Alpha-methylacetyl-CoA Alpha-methylacetyl-Coenzyme A N-Propionyl-CoA Propanoyl-CoA Propanoyl-Coenzyme A Propionyl-CoA Propionyl-coenzyme A α-Methylacetyl-CoA α-Methylacetyl-coenzyme A C24H40N7O17P3S 823.597 823.141423115 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-[(2-{[2-(propanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid propionyl-coa 317-66-8 CCC(=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/C24H40N7O17P3S/c1-4-15(33)52-8-7-26-14(32)5-6-27-22(36)19(35)24(2,3)10-45-51(42,43)48-50(40,41)44-9-13-18(47-49(37,38)39)17(34)23(46-13)31-12-30-16-20(25)28-11-29-21(16)31/h11-13,17-19,23,34-35H,4-10H2,1-3H3,(H,26,32)(H,27,36)(H,40,41)(H,42,43)(H2,25,28,29)(H2,37,38,39)/t13-,17-,18-,19?,23-/m1/s1 QAQREVBBADEHPA-UXYNFSPESA-N Solid Cytosol logp -0.31 ALOGPS logs -2.29 ALOGPS solubility 4.27e+00 g/l ALOGPS logp -5.2 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.01 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-[(2-{[2-(propanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 823.597 ChemAxon mono_mass 823.141423115 ChemAxon smiles CCC(=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 C24H40N7O17P3S ChemAxon inchi InChI=1S/C24H40N7O17P3S/c1-4-15(33)52-8-7-26-14(32)5-6-27-22(36)19(35)24(2,3)10-45-51(42,43)48-50(40,41)44-9-13-18(47-49(37,38)39)17(34)23(46-13)31-12-30-16-20(25)28-11-29-21(16)31/h11-13,17-19,23,34-35H,4-10H2,1-3H3,(H,26,32)(H,27,36)(H,40,41)(H,42,43)(H2,25,28,29)(H2,37,38,39)/t13-,17-,18-,19?,23-/m1/s1 ChemAxon inchikey QAQREVBBADEHPA-UXYNFSPESA-N ChemAxon polar_surface_area 363.63 ChemAxon refractivity 176.83 ChemAxon polarizability 74.37 ChemAxon rotatable_bond_count 21 ChemAxon acceptor_count 17 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Reductive carboxylate cycle (CO2 fixation) ec00720 C5-Branched dibasic acid metabolism ec00660 Glyoxylate and dicarboxylate metabolism ec00630 Glycerolipid metabolism ec00561 beta-Alanine metabolism The Beta-Alanine Metabolism starts with a product of Aspartate metabolism. Aspartate is decarboxylated by aspartate 1-decarboxylase, releasing carbon dioxide and Beta-alanine. Beta alanine is then metabolized through a pantothenate synthetase resulting in Pantothenic acid undergoes phosphorylation through a ATP driven pantothenate kinase, resulting in D-4-phosphopantothenate. Pantothenate (vitamin B5) is the universal precursor for the synthesis of the 4'-phosphopantetheine moiety of coenzyme A and acyl carrier protein. Only plants and microorganismscan synthesize pantothenate de novo - animals require a dietary supplement. The enzymes of this pathway are therefore considered to be antimicrobial drug targets. PW000896 ec00410 Metabolic 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 Metabolic pathways eco01100 Conversion of Succinate to Propanoate Based on the biochemical functions of a set of enzymes encoded within an operon, the existence of this pathway, resulting in net decarboxylation of succinate to propionate, has been proposed. However, no metabolic role for this pathway was shown. (EcoCyc) PW002058 Metabolic propanoyl CoA degradation The degradation of propanoyl-CoA starts with propanoyl-CoA undergoing a decarboxylase reaction by reacting with hydrogen carbonate and ATP resulting in the release of a phosphate, an ADP, a hydrogen ion and an S-methylmalonyl-CoA. This compound in turn reacts through an epimerase reaction resulting in the release of a R-methylmalonyl-CoA. This compound in turn can undergo a reversible reaction through a methylmalonyl-CoA mutase resulting in the release of a succinyl-CoA. This compound can be converted back to R-methylmalonyl-CoA through a methylmalonyl-CoA mutase. Methylmalonyl-CoA can then be converted into propanoyl-CoA through a methylmalonyl CoA decarboxylase . This compound in turn reacts with a succinate through a propionyl-CoA succinate CoA transferase resulting in the release of a propanoate and a succinyl-CoA. PW002057 Metabolic threonine degradation I PWY-5437 2-methylcitrate cycle I PWY0-42 conversion of succinate to propionate PWY0-43 methylmalonyl pathway PROPIONMET-PWY Specdb::CMs 791411 Specdb::CMs 791412 Specdb::CMs 791413 Specdb::CMs 791414 Specdb::CMs 791415 Specdb::CMs 791416 Specdb::CMs 791417 Specdb::CMs 791418 Specdb::NmrOneD 87692 Specdb::NmrOneD 87693 Specdb::NmrOneD 87694 Specdb::NmrOneD 87695 Specdb::NmrOneD 87696 Specdb::NmrOneD 87697 Specdb::NmrOneD 87698 Specdb::NmrOneD 87699 Specdb::NmrOneD 87700 Specdb::NmrOneD 87701 Specdb::NmrOneD 87702 Specdb::NmrOneD 87703 Specdb::NmrOneD 87704 Specdb::NmrOneD 87705 Specdb::NmrOneD 87706 Specdb::NmrOneD 87707 Specdb::NmrOneD 87708 Specdb::NmrOneD 87709 Specdb::NmrOneD 87710 Specdb::NmrOneD 87711 Specdb::MsMs 22970 Specdb::MsMs 22971 Specdb::MsMs 22972 Specdb::MsMs 29768 Specdb::MsMs 29769 Specdb::MsMs 29770 Specdb::MsMs 2299857 Specdb::MsMs 2299858 Specdb::MsMs 2299859 Specdb::MsMs 2638648 Specdb::MsMs 2638649 Specdb::MsMs 2638650 HMDB01275 439164 388310 C00100 15539 PROPIONYL-COA Propionyl-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 van 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. 17765195 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 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Sokatch, John R.; Sanders, Lois E.; Marshall, Vincent P. Oxidation of methylmalonate semialdehyde to propionyl coenzyme A in Pseudomonas aeruginosa grown on valine. Journal of Biological Chemistry (1968), 243(10), 2500-6. Formate acetyltransferase 1 P09373 PFLB_ECOLI pflB http://ecmdb.ca/proteins/P09373.xml Phosphate acetyltransferase P0A9M8 PTA_ECOLI pta http://ecmdb.ca/proteins/P0A9M8.xml Pyruvate formate-lyase 1-activating enzyme P0A9N4 PFLA_ECOLI pflA http://ecmdb.ca/proteins/P0A9N4.xml 3-ketoacyl-CoA thiolase P21151 FADA_ECOLI fadA http://ecmdb.ca/proteins/P21151.xml Acetyl-coenzyme A synthetase P27550 ACSA_ECOLI acs http://ecmdb.ca/proteins/P27550.xml 2-methylcitrate synthase P31660 PRPC_ECOLI prpC http://ecmdb.ca/proteins/P31660.xml Formate acetyltransferase 2 P32674 PFLD_ECOLI pflD http://ecmdb.ca/proteins/P32674.xml Keto-acid formate acetyltransferase P42632 TDCE_ECOLI tdcE http://ecmdb.ca/proteins/P42632.xml Methylmalonyl-CoA decarboxylase P52045 MMCD_ECOLI mmcD http://ecmdb.ca/proteins/P52045.xml Putative formate acetyltransferase 3 P75793 PFLF_ECOLI ybiW http://ecmdb.ca/proteins/P75793.xml 3-ketoacyl-CoA thiolase_ P76503 FADI_ECOLI fadI http://ecmdb.ca/proteins/P76503.xml Propionate--CoA ligase P77495 PRPE_ECOLI prpE http://ecmdb.ca/proteins/P77495.xml Uncharacterized protein ygfH P52043 YGFH_ECOLI ygfH http://ecmdb.ca/proteins/P52043.xml Autonomous glycyl radical cofactor P68066 GRCA_ECOLI grcA http://ecmdb.ca/proteins/P68066.xml Water + Oxalacetic acid + Propionyl-CoA <> Methylcitric acid + Coenzyme A + Hydrogen ion + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate R00931 2-METHYLCITRATE-SYNTHASE-RXN Phosphate + Propionyl-CoA > Coenzyme A + Propanoyl phosphate R00921 PTAALT-RXN Hydrogen ion + (S)-Methylmalonyl-CoA <> Carbon dioxide + Propionyl-CoA R00923 Propionyl-CoA + Succinic acid > Propionic acid + Succinyl-CoA RXN0-268 Adenosine triphosphate + Coenzyme A + Propionic acid > ADP + Phosphate + Propionyl-CoA Propionyl-CoA + Phosphate <> Propanoyl phosphate + Coenzyme A R00921 (S)-Methylmalonyl-CoA <> Propionyl-CoA + Carbon dioxide R00923 Propinol adenylate + Coenzyme A <> Adenosine monophosphate + Propionyl-CoA R00926 Propionyl-CoA + Acetyl-CoA <> Coenzyme A + 2-Methylacetoacetyl-CoA R00927 Methylcitric acid + Coenzyme A <> Propionyl-CoA + Oxalacetic acid + Water R00931 Propionyl-CoA + Chenodeoxycholoyl-CoA <> Coenzyme A + 3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA R04546 2-Ketobutyric acid + Coenzyme A <> Propionyl-CoA + Formic acid R06987 Oxalacetic acid + Water + Propionyl-CoA <> Hydrogen ion + Methylcitric acid + Coenzyme A 2-METHYLCITRATE-SYNTHASE-RXN Propionyl-CoA + Water + Glyoxylic acid <> 2-hydroxyglutarate + Hydrogen ion + Coenzyme A HYDGLUTSYN-RXN 2-Ketobutyric acid + Coenzyme A > Propionyl-CoA + Formic acid KETOBUTFORMLY-RXN Coenzyme A + Propionic acid + Adenosine triphosphate > Propionyl-CoA + Pyrophosphate + Adenosine monophosphate PROPIONATE--COA-LIGASE-RXN Adenosine triphosphate + Hydrogen carbonate + Propionyl-CoA > Hydrogen ion + ADP + Phosphate + (S)-Methylmalonyl-CoA PROPIONYL-COA-CARBOXY-RXN Propionyl-CoA + Succinic acid <> Propionic acid + Succinyl-CoA RXN0-268 Hydrogen ion + R-Methylmalonyl-CoA > Propionyl-CoA + Carbon dioxide RXN0-310 Propionyl-CoA + Water + Oxalacetic acid > (2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate + CoA Adenosine triphosphate + Propionic acid + CoA > Adenosine monophosphate + Pyrophosphate + Propionyl-CoA (S)-Methylmalonyl-CoA > Propionyl-CoA + Carbon dioxide Propionyl-CoA + Formic acid > CoA + 2-Ketobutyric acid Propionyl-CoA + NADP <> Acrylyl-CoA + NADPH + Hydrogen ion R00919 Adenosine triphosphate + Propionic acid + Coenzyme A <> Adenosine monophosphate + Pyrophosphate + Propionyl-CoA R00925 2-Ketobutyric acid + Coenzyme A > Formic acid + Propionyl-CoA + Propionyl-CoA PW_R003493 Propionyl-CoA + Phosphate + Propionyl-CoA > Coenzyme A + propanoyl phosphate + Propanoyl phosphate PW_R003494 Propionic acid + Adenosine triphosphate + Coenzyme A > Propionyl-CoA + Adenosine monophosphate + Pyrophosphate + Propionyl-CoA PW_R003496 Propionyl-CoA + Water + Oxalacetic acid + Propionyl-CoA > Coenzyme A + Hydrogen ion + 2-Methylcitric acid + Methylcitric acid PW_R003497 Succinic acid + Propionyl-CoA + Propionyl-CoA > Propionic acid + Succinyl-CoA + Succinyl-CoA PW_R003501 Methylmalonyl-CoA + Hydrogen ion > Carbon dioxide + Propionyl-CoA + Propionyl-CoA PW_R003503 R-Methylmalonyl-CoA + Hydrogen ion > Propionyl-CoA + Carbon dioxide PW_R006008 Water + Oxalacetic acid + Propionyl-CoA <> Methylcitric acid + Coenzyme A + Hydrogen ion + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate Phosphate + Propionyl-CoA > Coenzyme A + Propanoyl phosphate Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 5.32 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 21280 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621