2.02012-05-31 10:24:28 -06002015-09-13 12:56:07 -0600ECMDB00237M2MDB000098Propionic acidPropionic acid (PA) is a naturally-occurring carboxylic acid with chemical formula CH3CH2COOH. It is a clear liquid with a pungent odor. The anion CH3CH2COOAdofeedAntischim BCarboxyethaneEthanecarboxylateEthanecarboxylic acidEthylformateEthylformic acidLuprosilMetacetonateMetacetonic acidMethylacetateMethylacetic acidMonoPropPropanatePropanic acidPropanoatePropanoic acidPropcornPropionatePropionic acidPropkornProzoinPseudoacetatePseudoacetic acidToxi-CheckC3H6O274.078574.036779436propanoic acidpropanoic acid79-09-4CCC(O)=OInChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)XBDQKXXYIPTUBI-UHFFFAOYSA-NLiquidCytosolExtra-organismPeriplasmlogp0.31logs0.68solubility3.52e+02 g/lmelting_point-20.7 oClogp0.48pka_strongest_acidic4.75iupacpropanoic acidaverage_mass74.0785mono_mass74.036779436smilesCCC(O)=OformulaC3H6O2inchiInChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)inchikeyXBDQKXXYIPTUBI-UHFFFAOYSA-Npolar_surface_area37.3refractivity17.27polarizability7.24rotatable_bond_count1acceptor_count2donor_count1physiological_charge-1formal_charge0Nicotinate and nicotinamide metabolismec00760Propanoate 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.PW000940ec00640MetabolicEthylbenzene degradationec00642Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100inner membrane transportlist 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 addedPW000786MetabolicConversion of Succinate to PropanoateBased 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)PW002058Metabolicpropanoyl CoA degradationThe 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.PW002057Metabolicthreonine degradation IPWY-54372-methylcitrate cycle IPWY0-42conversion of succinate to propionatePWY0-43Specdb::CMs3102Specdb::CMs28069Specdb::CMs29451Specdb::CMs37378Specdb::CMs99551Specdb::CMs99552Specdb::CMs133887Specdb::CMs141621Specdb::CMs1055133Specdb::EiMs1331Specdb::NmrOneD1213Specdb::NmrOneD1257Specdb::NmrOneD2649Specdb::NmrOneD3335Specdb::NmrOneD4982Specdb::NmrOneD4983Specdb::NmrOneD166487Specdb::MsMs397Specdb::MsMs398Specdb::MsMs399Specdb::MsMs3714Specdb::MsMs3715Specdb::MsMs3716Specdb::MsMs3717Specdb::MsMs3718Specdb::MsMs3719Specdb::MsMs20645Specdb::MsMs20646Specdb::MsMs20647Specdb::MsMs20729Specdb::MsMs20730Specdb::MsMs20731Specdb::MsMs22196Specdb::MsMs22197Specdb::MsMs22198Specdb::MsMs22280Specdb::MsMs22281Specdb::MsMs22282Specdb::MsMs438245Specdb::MsMs438246Specdb::MsMs438247Specdb::MsMs438248Specdb::NmrTwoD1005Specdb::NmrTwoD1229HMDB0023710321005C0016330768PROPIONATEPPIPropionic acidKeseler, 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?1358895483Acetate kinaseP0A6A3ACKA_ECOLIackAhttp://ecmdb.ca/proteins/P0A6A3.xmlPropionate kinaseP11868TDCD_ECOLItdcDhttp://ecmdb.ca/proteins/P11868.xmlAcetyl-coenzyme A synthetaseP27550ACSA_ECOLIacshttp://ecmdb.ca/proteins/P27550.xmlAldehyde dehydrogenase BP37685ALDB_ECOLIaldBhttp://ecmdb.ca/proteins/P37685.xmlPropionate--CoA ligaseP77495PRPE_ECOLIprpEhttp://ecmdb.ca/proteins/P77495.xmlUncharacterized protein ygfHP52043YGFH_ECOLIygfHhttp://ecmdb.ca/proteins/P52043.xmlShort-chain fatty acids transporterP76460ATOE_ECOLIatoEhttp://ecmdb.ca/proteins/P76460.xmlSodium/proline symporterP07117PUTP_ECOLIputPhttp://ecmdb.ca/proteins/P07117.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlPropionyl-CoA + Succinic acid > Propionic acid + Succinyl-CoARXN0-268ADP + Propanoyl phosphate <> Adenosine triphosphate + Propionic acidR01353PROPKIN-RXNWater + NADP + Propanal >2 Hydrogen ion + NADPH + Propionic acidAdenosine triphosphate + Coenzyme A + Propionic acid > ADP + Phosphate + Propionyl-CoAAdenosine triphosphate + Propionic acid <> ADP + Propanoyl phosphateR01353Adenosine triphosphate + Propionic acid <> Pyrophosphate + Propinol adenylateR01354Coenzyme A + Propionic acid + Adenosine triphosphate > Propionyl-CoA + Pyrophosphate + Adenosine monophosphatePROPIONATE--COA-LIGASE-RXNPropionyl-CoA + Succinic acid <> Propionic acid + Succinyl-CoARXN0-268Adenosine triphosphate + Propionic acid > ADP + Propanoyl phosphateAdenosine triphosphate + Propionic acid + CoA > Adenosine monophosphate + Pyrophosphate + Propionyl-CoAAdenosine triphosphate + Propionic acid + Coenzyme A <> Adenosine monophosphate + Pyrophosphate + Propionyl-CoAR00925 Adenosine diphosphate + propanoyl phosphate + ADP + Propanoyl phosphate > Adenosine triphosphate + Propionic acidPW_R003495Propionic acid + Adenosine triphosphate + Coenzyme A > Propionyl-CoA + Adenosine monophosphate + Pyrophosphate + Propionyl-CoAPW_R003496Succinic acid + Propionyl-CoA + Propionyl-CoA > Propionic acid + Succinyl-CoA + Succinyl-CoAPW_R003501