2.0 2012-05-31 10:24:28 -0600 2015-09-13 12:56:07 -0600 ECMDB00237 M2MDB000098 Propionic acid Propionic acid (PA) is a naturally-occurring carboxylic acid with chemical formula CH3CH2COOH. It is a clear liquid with a pungent odor. The anion CH3CH2COO Adofeed Antischim B Carboxyethane Ethanecarboxylate Ethanecarboxylic acid Ethylformate Ethylformic acid Luprosil Metacetonate Metacetonic acid Methylacetate Methylacetic acid MonoProp Propanate Propanic acid Propanoate Propanoic acid Propcorn Propionate Propionic acid Propkorn Prozoin Pseudoacetate Pseudoacetic acid Toxi-Check C3H6O2 74.0785 74.036779436 propanoic acid propanoic acid 79-09-4 CCC(O)=O InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5) XBDQKXXYIPTUBI-UHFFFAOYSA-N Liquid Cytosol Extra-organism Periplasm logp 0.31 ALOGPS logs 0.68 ALOGPS solubility 3.52e+02 g/l ALOGPS melting_point -20.7 oC logp 0.48 ChemAxon pka_strongest_acidic 4.75 ChemAxon iupac propanoic acid ChemAxon average_mass 74.0785 ChemAxon mono_mass 74.036779436 ChemAxon smiles CCC(O)=O ChemAxon formula C3H6O2 ChemAxon inchi InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5) ChemAxon inchikey XBDQKXXYIPTUBI-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 17.27 ChemAxon polarizability 7.24 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Nicotinate and nicotinamide metabolism ec00760 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 Ethylbenzene degradation ec00642 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic 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 Specdb::CMs 3102 Specdb::CMs 28069 Specdb::CMs 29451 Specdb::CMs 37378 Specdb::CMs 99551 Specdb::CMs 99552 Specdb::CMs 133887 Specdb::CMs 141621 Specdb::CMs 1055133 Specdb::EiMs 1331 Specdb::NmrOneD 1213 Specdb::NmrOneD 1257 Specdb::NmrOneD 2649 Specdb::NmrOneD 3335 Specdb::NmrOneD 4982 Specdb::NmrOneD 4983 Specdb::NmrOneD 166487 Specdb::MsMs 397 Specdb::MsMs 398 Specdb::MsMs 399 Specdb::MsMs 3714 Specdb::MsMs 3715 Specdb::MsMs 3716 Specdb::MsMs 3717 Specdb::MsMs 3718 Specdb::MsMs 3719 Specdb::MsMs 20645 Specdb::MsMs 20646 Specdb::MsMs 20647 Specdb::MsMs 20729 Specdb::MsMs 20730 Specdb::MsMs 20731 Specdb::MsMs 22196 Specdb::MsMs 22197 Specdb::MsMs 22198 Specdb::MsMs 22280 Specdb::MsMs 22281 Specdb::MsMs 22282 Specdb::MsMs 438245 Specdb::MsMs 438246 Specdb::MsMs 438247 Specdb::MsMs 438248 Specdb::NmrTwoD 1005 Specdb::NmrTwoD 1229 HMDB00237 1032 1005 C00163 30768 PROPIONATE PPI Propionic acid Keseler, I. 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Shihua Jishu Yu Yingyong (2005), 23(6), 421-423. http://hmdb.ca/system/metabolites/msds/000/000/172/original/HMDB00237.pdf?1358895483 Acetate kinase P0A6A3 ACKA_ECOLI ackA http://ecmdb.ca/proteins/P0A6A3.xml Propionate kinase P11868 TDCD_ECOLI tdcD http://ecmdb.ca/proteins/P11868.xml Acetyl-coenzyme A synthetase P27550 ACSA_ECOLI acs http://ecmdb.ca/proteins/P27550.xml Aldehyde dehydrogenase B P37685 ALDB_ECOLI aldB http://ecmdb.ca/proteins/P37685.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 Short-chain fatty acids transporter P76460 ATOE_ECOLI atoE http://ecmdb.ca/proteins/P76460.xml Sodium/proline symporter P07117 PUTP_ECOLI putP http://ecmdb.ca/proteins/P07117.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Propionyl-CoA + Succinic acid > Propionic acid + Succinyl-CoA RXN0-268 ADP + Propanoyl phosphate <> Adenosine triphosphate + Propionic acid R01353 PROPKIN-RXN Water + NADP + Propanal >2 Hydrogen ion + NADPH + Propionic acid Adenosine triphosphate + Coenzyme A + Propionic acid > ADP + Phosphate + Propionyl-CoA Adenosine triphosphate + Propionic acid <> ADP + Propanoyl phosphate R01353 Adenosine triphosphate + Propionic acid <> Pyrophosphate + Propinol adenylate R01354 Coenzyme A + Propionic acid + Adenosine triphosphate > Propionyl-CoA + Pyrophosphate + Adenosine monophosphate PROPIONATE--COA-LIGASE-RXN Propionyl-CoA + Succinic acid <> Propionic acid + Succinyl-CoA RXN0-268 Adenosine triphosphate + Propionic acid > ADP + Propanoyl phosphate Adenosine triphosphate + Propionic acid + CoA > Adenosine monophosphate + Pyrophosphate + Propionyl-CoA Adenosine triphosphate + Propionic acid + Coenzyme A <> Adenosine monophosphate + Pyrophosphate + Propionyl-CoA R00925 Adenosine diphosphate + propanoyl phosphate + ADP + Propanoyl phosphate > Adenosine triphosphate + Propionic acid PW_R003495 Propionic acid + Adenosine triphosphate + Coenzyme A > Propionyl-CoA + Adenosine monophosphate + Pyrophosphate + Propionyl-CoA PW_R003496 Succinic acid + Propionyl-CoA + Propionyl-CoA > Propionic acid + Succinyl-CoA + Succinyl-CoA PW_R003501