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propionic acid (YMDB00857)

Identification
YMDB IDYMDB00857
Namepropionic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPropionic acid, also known as acide propanoique or propionate, 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. Propionic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Propionic acid exists in all living species, ranging from bacteria to humans. Propionic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • acide propanoique
  • Carboxyethane
  • Ethanecarboxylate
  • Ethanecarboxylic acid
  • Ethylformate
  • Ethylformic acid
  • Kyselina propionova
  • Luprisol
  • Luprosil
  • Metacetonate
  • Metacetonic acid
  • Methylacetate
  • Methylacetic acid
  • MonoProp
  • n-propionic acid
  • PA
  • propanate
  • propanoate
  • propanoic acid
  • Propcorn
  • propioic acid
  • Propionate
  • Propionic acid
  • Propionsaeure
  • Propkorn
  • propoic acid
  • Prozoin
  • Pseudoacetate
  • Pseudoacetic acid
  • Acide propionique
  • CH3-CH2-COOH
  • Propioate
  • Propoate
  • Adofeed
  • Antischim b
  • Toxi-check
  • Propionic acid, zinc salt
  • Potassium propionate
  • Chromium propionate
  • Lithium propanoate
  • Zinc propionate
CAS number79-09-4
WeightAverage: 74.0785
Monoisotopic: 74.036779436
InChI KeyXBDQKXXYIPTUBI-UHFFFAOYSA-N
InChIInChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
IUPAC Namepropanoic acid
Traditional IUPAC Namepropanoic acid
Chemical FormulaC3H6O2
SMILESCCC(O)=O
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
Physical Properties
StateLiquid
Charge0
Melting point-20.7 °C
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL at 25 oC [US EPA (1981)]PhysProp
LogP0.33 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility352 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
AcidicFDB031132
CheesyFDB031132
PungentFDB031132
RancidFDB031132
SoyFDB031132
VinegarFDB031132
SMPDB PathwaysNot Available
KEGG Pathways
Nicotinate and nicotinamide metabolismec00760 Map00760
Propanoate metabolismec00640 Map00640
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-51f674be972a6c17185bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-691dcd080b30c9898350JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-51f674be972a6c17185bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-691dcd080b30c9898350JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00b9-9000000000-abf322c73e6badb078bfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9100000000-cbfe9e32208652e70047JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-9000000000-1af60fc458a7f351a9b0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-aa6e765fc867ac8be641JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-27e0b790e192d1304449JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-004i-9000000000-51f674be972a6c17185bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-004i-9000000000-90d9e0181596093a2f85JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-bdd7baa3d1bda886fb77JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-e73379c8765802cf3228JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-d6832c04c8b2ca0fdfa3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-d0c93844dbfaed791bb0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-bdd7baa3d1bda886fb77JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-e73379c8765802cf3228JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-d6832c04c8b2ca0fdfa3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-d0c93844dbfaed791bb0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-47364fadf00a5a2b7e93JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-76fad523c005a6510264JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-a1c0234da57ff32c6e12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-47364fadf00a5a2b7e93JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-76fad523c005a6510264JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-a1c0234da57ff32c6e12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-db59da781a70634d2526JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9000000000-bea4ff21e6ab6c664412JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-782832f8f5ab85f2ef4fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-db59da781a70634d2526JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9000000000-bea4ff21e6ab6c664412JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-782832f8f5ab85f2ef4fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00b9-9000000000-0bb3297c4159bed2316eJSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Patel, S. S., Walt, D. R. (1987). "Substrate specificity of acetyl coenzyme A synthetase." J Biol Chem 262:7132-7134.2884217
Synthesis Reference:Zhan, Jianghong; Meng, Wei; Gong, Tao; Huang, Fen-sheng. Preparation of propionic acid by propionaldehyde oxidation. Shihua Jishu Yu Yingyong (2005), 23(6), 421-423.
External Links:
ResourceLink
CHEBI ID30768
HMDB IDHMDB00237
Pubchem Compound ID1032
Kegg IDC00163
ChemSpider ID1005
FOODB IDFDB031132
WikipediaPropanoic_acid
BioCyc IDPROPIONATE

Enzymes

Protein Details
1. Acetyl-coenzyme A synthetase 1
General function:
Involved in acetate-CoA ligase activity
Specific function:
Catalyzes the production of acetyl-CoA. Provides the acetyl-CoA source for histone acetylation in the nucleus. "Aerobic" isozyme of acetyl-coenzyme A synthetase, which supports growth on nonfermentable carbon sources such as glycerol and ethanol. May be required for assimilation of ethanol and acetate
Gene Name:
ACS1
Uniprot ID:
Q01574
Molecular weight:
79140.10156
Reactions
ATP + acetate + CoA → AMP + diphosphate + acetyl-CoA.
Protein Details
2. Acetyl-coenzyme A synthetase 2
General function:
Involved in acetate-CoA ligase activity
Specific function:
Catalyzes the production of acetyl-CoA. Provides the acetyl-CoA source for histone acetylation in the nucleus. "Anaerobic" isozyme of acetyl-coenzyme A synthetase, which is required for growth on fermentable carbon sources such as glucose. May be involved in the PDH (pyruvate dehydrogenase complex) bypass
Gene Name:
ACS2
Uniprot ID:
P52910
Molecular weight:
75491.10156
Reactions
ATP + acetate + CoA → AMP + diphosphate + acetyl-CoA.