You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Livestock Metabolome Database.
Record Information
Version1.0
Creation Date2016-07-13 19:42:35 UTC
Update Date2016-09-23 18:44:43 UTC
LmdbLMDB00110
Secondary Accession NumbersNone
Metabolite Identification
Common NamePropionic acid
DescriptionPropionic acid (PA) is widely used as an antifungal agent in food. It is present naturally at low levels in dairy products and occurs ubiquitously, together with other short-chain fatty acids (SCFA), in the gastro-intestinal tract of animals and other mammals as an end-product of the microbial digestion of carbohydrates. It has significant physiological activity in animals. PA is irritant but produces no acute systemic effects and has no demonstrable genotoxic potential. (PMID 1628870 ) Propionic aciduria is one of the most frequent organic acidurias, a disease that comprise many various disorders. The outcome of patients born with Propionic aciduria is poor intellectual development patterns, with 60% having an IQ less than 75 and requiring special education. Successful liver and/or renal transplantations, in a few patients, have resulted in better quality of life but have not necessarily prevented neurological and various visceral complications. These results emphasize the need for permanent metabolic follow-up whatever the therapeutic strategy. (PMID 15868474 ) Decreased early mortality, less severe symptoms at diagnosis, and more favorable short-term neurodevelopmental outcome were recorded in patients identified through expanded newborn screening. (PMID 16763906 ).
Structure
Thumb
Synonyms
ValueSource
Acide propanoiqueChEBI
Acide propioniqueChEBI
CarboxyethaneChEBI
CH3-CH2-COOHChEBI
Ethanecarboxylic acidChEBI
Ethylformic acidChEBI
Metacetonic acidChEBI
Methylacetic acidChEBI
PAChEBI
Propanoic acidChEBI
Propioic acidChEBI
PropionsaeureChEBI
Propoic acidChEBI
Pseudoacetic acidChEBI
PropionateKegg
EthanecarboxylateGenerator
EthylformateGenerator
MetacetonateGenerator
MethylacetateGenerator
PropanoateGenerator
PropioateGenerator
PropoateGenerator
PseudoacetateGenerator
AdofeedHMDB
Antischim bHMDB
LuprosilHMDB
MonoPropHMDB
PropanateHMDB
PropcornHMDB
PropkornHMDB
ProzoinHMDB
Toxi-checkHMDB
Propionic acid, zinc saltHMDB
Potassium propionateHMDB
Chromium propionateHMDB
Lithium propanoateHMDB
Zinc propionateHMDB
Chemical FormulaC3H6O2
Average Molecular Weight74.0785
Monoisotopic Molecular Weight74.036779436
IUPAC Namepropanoic acid
Traditional Namepropanoic acid
CAS Registry Number79-09-4
SMILES
CCC(O)=O
InChI Identifier
InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
InChI KeyXBDQKXXYIPTUBI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.31ALOGPS
logP0.48ChemAxon
logS0.68ALOGPS
pKa (Strongest Acidic)4.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.27 m³·mol⁻¹ChemAxon
Polarizability7.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-51f674be972a6c17185bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-691dcd080b30c9898350Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-51f674be972a6c17185bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-691dcd080b30c9898350Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00b9-9000000000-abf322c73e6badb078bfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9100000000-cbfe9e32208652e70047Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-bdd7baa3d1bda886fb77Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-e73379c8765802cf3228Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-d6832c04c8b2ca0fdfa3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-d0c93844dbfaed791bb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-bdd7baa3d1bda886fb77Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-e73379c8765802cf3228Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-d6832c04c8b2ca0fdfa3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-d0c93844dbfaed791bb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-9000000000-1af60fc458a7f351a9b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-aa6e765fc867ac8be641Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-27e0b790e192d1304449Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-004i-9000000000-51f674be972a6c17185bSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-004i-9000000000-90d9e0181596093a2f85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-db59da781a70634d2526Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9000000000-bea4ff21e6ab6c664412Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-782832f8f5ab85f2ef4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-db59da781a70634d2526Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9000000000-bea4ff21e6ab6c664412Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-782832f8f5ab85f2ef4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-a18665b48b96b6efae4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-8055e7a3b8461624b359Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-3213178acf8c2ee6fe55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-47364fadf00a5a2b7e93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-76fad523c005a6510264Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-a1c0234da57ff32c6e12Spectrum
MSMass Spectrum (Electron Ionization)splash10-00b9-9000000000-0bb3297c4159bed2316eSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Colostrum
  • Feces
  • Meat
  • Plasma
  • Rumen
  • Ruminal Fluid
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
RumenDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Hanne Christine B...
details
Ruminal FluidDetected and Quantified134000 uMNot AvailableOvine
    • M.L.K. Bonsi, P.O...
details
Ruminal FluidDetected and Quantified146000-153000 uMNot AvailableOvine
    • M.L.K. Bonsi, P.O...
details
Ruminal FluidDetected and Quantified156000-162000 uMNot AvailableOvine
    • M.L.K. Bonsi, P.O...
details
Ruminal FluidDetected and Quantified16,000 +/- 2,000 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified16,860 +/- 5,180 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified16,860 +/- 5,180 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified18,210 +/- 3,210 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified22,630 +/- 8,030 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified31,835 +/- 6,795 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified15000 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified17900 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified18000 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified27600 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified16800 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified18200 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified15200 +/- 1000 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified22600 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified15800 +/- 900 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified31800 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified15900 +/- 1300 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified12310 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified12770 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified14110 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified14700 +/- 300 uMNot AvailableCaprine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDDB03766
HMDB IDHMDB0000237
FooDB IDFDB031132
Phenol Explorer IDNot Available
KNApSAcK IDC00044287
BiGG ID34098
BioCyc IDPROPIONATE
METLIN ID3215
PDB IDNot Available
Wikipedia LinkPropionic acid
Chemspider ID1005
ChEBI ID30768
PubChem Compound ID1032
Kegg Compound IDC00163
YMDB IDYMDB00857
ECMDB IDECMDB00237
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Harrison PT: Propionic acid and the phenomenon of rodent forestomach tumorigenesis: a review. Food Chem Toxicol. 1992 Apr;30(4):333-40. [1628870 ]
  2. de Baulny HO, Benoist JF, Rigal O, Touati G, Rabier D, Saudubray JM: Methylmalonic and propionic acidaemias: management and outcome. J Inherit Metab Dis. 2005;28(3):415-23. [15868474 ]
  3. Dionisi-Vici C, Deodato F, Roschinger W, Rhead W, Wilcken B: 'Classical' organic acidurias, propionic aciduria, methylmalonic aciduria and isovaleric aciduria: long-term outcome and effects of expanded newborn screening using tandem mass spectrometry. J Inherit Metab Dis. 2006 Apr-Jun;29(2-3):383-9. [16763906 ]