Propionic acid (PAMDB000098)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000098
Identification
Name: Propionic acid
Description: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
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 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
Chemical Formula: C3H6O2
Average Molecular Weight: 74.0785
Monoisotopic Molecular Weight: 74.036779436
InChI Key: XBDQKXXYIPTUBI-UHFFFAOYSA-N
InChI:InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
CAS number: 79-09-4
IUPAC Name:propanoic acid
Traditional IUPAC Name: propanoic acid
SMILES:CCC(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct Parent Carboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:-1
Melting point: -20.7 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/mL [US EPA (1981)]PhysProp
LogP:0.33 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility352.0 mg/mLALOGPS
logP0.31ALOGPS
logP0.48ChemAxon
logS0.68ALOGPS
pKa (Strongest Acidic)4.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.27 m3·mol-1ChemAxon
Polarizability7.24 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Propionyl-CoA + Succinic acid > Propionic acid + Succinyl-CoA
Water + NADP + Propanal >2 Hydrogen ion + NADPH + Propionic acid
Adenosine triphosphate + Coenzyme A + Propionic acid > ADP + Phosphate + Propionyl-CoA
Coenzyme A + Propionic acid + Adenosine triphosphate > Propionyl-CoA + Pyrophosphate + Adenosine monophosphate
Adenosine triphosphate + Propionic acid <> ADP + Propanoyl phosphate
Adenosine diphosphate + propanoyl phosphate + ADP + Propanoyl phosphate > Adenosine triphosphate + Propionic acid
Propionic acid + Adenosine triphosphate + Coenzyme A > Propionyl-CoA + Adenosine monophosphate + Pyrophosphate + Propionyl-CoA
Succinic acid + Propionyl-CoA + Propionyl-CoA > Propionic acid + Succinyl-CoA + Succinyl-CoA
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-9000000000-1af60fc458a7f351a9b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-aa6e765fc867ac8be641View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-27e0b790e192d1304449View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-004i-9000000000-51f674be972a6c17185bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-004i-9000000000-90d9e0181596093a2f85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-bdd7baa3d1bda886fb77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-e73379c8765802cf3228View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-d6832c04c8b2ca0fdfa3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-d0c93844dbfaed791bb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-47364fadf00a5a2b7e93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-76fad523c005a6510264View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-a1c0234da57ff32c6e12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-47364fadf00a5a2b7e93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-76fad523c005a6510264View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-a1c0234da57ff32c6e12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-db59da781a70634d2526View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9000000000-bea4ff21e6ab6c664412View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-782832f8f5ab85f2ef4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-db59da781a70634d2526View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9000000000-bea4ff21e6ab6c664412View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-782832f8f5ab85f2ef4fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00b9-9000000000-0bb3297c4159bed2316eView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Alekseev OM, Widgren EE, Richardson RT, O'Rand MG: Association of NASP with HSP90 in mouse spermatogenic cells: stimulation of ATPase activity and transport of linker histones into nuclei. J Biol Chem. 2005 Jan 28;280(4):2904-11. Epub 2004 Nov 8. Pubmed: 15533935
  • Beutler KT, Pankewycz O, Brautigan DL: Equivalent uptake of organic and inorganic zinc by monkey kidney fibroblasts, human intestinal epithelial cells, or perfused mouse intestine. Biol Trace Elem Res. 1998 Jan;61(1):19-31. Pubmed: 9498328
  • Bintvihok A, Kositcharoenkul S: Effect of dietary calcium propionate on performance, hepatic enzyme activities and aflatoxin residues in broilers fed a diet containing low levels of aflatoxin B1. Toxicon. 2006 Jan;47(1):41-6. Epub 2005 Nov 18. Pubmed: 16298407
  • Chandler RJ, Aswani V, Tsai MS, Falk M, Wehrli N, Stabler S, Allen R, Sedensky M, Kazazian HH, Venditti CP: Propionyl-CoA and adenosylcobalamin metabolism in Caenorhabditis elegans: evidence for a role of methylmalonyl-CoA epimerase in intermediary metabolism. Mol Genet Metab. 2006 Sep-Oct;89(1-2):64-73. Epub 2006 Jul 14. Pubmed: 16843692
  • Christensen JK, Varming T, Ahring PK, Jorgensen TD, Nielsen EO: In vitro characterization of 5-carboxyl-2,4-di-benzamidobenzoic acid (NS3763), a noncompetitive antagonist of GLUK5 receptors. J Pharmacol Exp Ther. 2004 Jun;309(3):1003-10. Epub 2004 Feb 25. Pubmed: 14985418
  • 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. Pubmed: 15868474
  • De Kanter R, De Jager MH, Draaisma AL, Jurva JU, Olinga P, Meijer DK, Groothuis GM: Drug-metabolizing activity of human and rat liver, lung, kidney and intestine slices. Xenobiotica. 2002 May;32(5):349-62. Pubmed: 12065058
  • 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. Pubmed: 16763906
  • Esposito BP, Faljoni-Alario A, de Menezes JF, de Brito HF, Najjar R: A circular dichroism and fluorescence quenching study of the interactions between rhodium(II) complexes and human serum albumin. J Inorg Biochem. 1999 May 30;75(1):55-61. Pubmed: 10402677
  • Harrison PT: Propionic acid and the phenomenon of rodent forestomach tumorigenesis: a review. Food Chem Toxicol. 1992 Apr;30(4):333-40. Pubmed: 1628870
  • Jeng JH, Chan CP, Ho YS, Lan WH, Hsieh CC, Chang MC: Effects of butyrate and propionate on the adhesion, growth, cell cycle kinetics, and protein synthesis of cultured human gingival fibroblasts. J Periodontol. 1999 Dec;70(12):1435-42. Pubmed: 10632518
  • 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. Pubmed: 22080510
  • 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. Pubmed: 21097882
  • Koeppe RA, Frey KA, Snyder SE, Meyer P, Kilbourn MR, Kuhl DE: Kinetic modeling of N-[11C]methylpiperidin-4-yl propionate: alternatives for analysis of an irreversible positron emission tomography trace for measurement of acetylcholinesterase activity in human brain. J Cereb Blood Flow Metab. 1999 Oct;19(10):1150-63. Pubmed: 10532640
  • Lin SC, Bergles DE: Synaptic signaling between neurons and glia. Glia. 2004 Aug 15;47(3):290-8. Pubmed: 15252819
  • Marala RB, Brown JA, Kong JX, Tracey WR, Knight DR, Wester RT, Sun D, Kennedy SP, Hamanaka ES, Ruggeri RB, Hill RJ: Zoniporide: a potent and highly selective inhibitor of human Na(+)/H(+) exchanger-1. Eur J Pharmacol. 2002 Sep 6;451(1):37-41. Pubmed: 12223226
  • Mayer B, Schumacher M, Brandstatter H, Wagner FS, Hermetter A: High-throughput fluorescence screening of antioxidative capacity in human serum. Anal Biochem. 2001 Oct 15;297(2):144-53. Pubmed: 11673881
  • Nguyen TB, Snyder SE, Kilbourn MR: Syntheses of carbon-11 labeled piperidine esters as potential in vivo substrates for acetylcholinesterase. Nucl Med Biol. 1998 Nov;25(8):761-8. Pubmed: 9863564
  • Ridge BD, Batt MD, Palmer HE, Jarrett A: The dansyl chloride technique for stratum corneum renewal as an indicator of changes in epidermal mitotic activity following topical treatment. Br J Dermatol. 1988 Feb;118(2):167-74. Pubmed: 3348963
  • Robertson MD, Bickerton AS, Dennis AL, Vidal H, Frayn KN: Insulin-sensitizing effects of dietary resistant starch and effects on skeletal muscle and adipose tissue metabolism. Am J Clin Nutr. 2005 Sep;82(3):559-67. Pubmed: 16155268
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Somerma S, Lassus A, Salde L: Assessment of atrophy of human skin caused by corticosteroids using chamber occlusion and suction blister techniques. Acta Derm Venereol. 1984;64(1):41-5. Pubmed: 6203280
  • 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. Pubmed: 17765195
  • Wendel U, Zass R, Leupold D: Contribution of odd-numbered fatty acid oxidation to propionate production in neonates with methylmalonic and propionic acidaemias. Eur J Pediatr. 1993 Dec;152(12):1021-3. Pubmed: 8131803
  • 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. Pubmed: 18331064
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.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID30768
HMDB IDHMDB00237
Pubchem Compound ID1032
Kegg IDC00163
ChemSpider ID1005
WikipediaPropionic acid
BioCyc IDPROPIONATE
EcoCyc IDPROPIONATE
Ligand ExpoPPI

Enzymes

Protein Details
• Acetate kinase
General function:
Involved in kinase activity
Specific function:
Involved in the activation of acetate to acetyl CoA and the secretion of acetate. During anaerobic growth of the organism, this enzyme is also involved in the synthesis of most of the ATP formed catabolically
Gene Name:
ackA
Locus Tag:
PA0836
Molecular weight:
42.4 kDa
Reactions
ATP + acetate = ADP + acetyl phosphate.
ATP + propanoate = ADP + propanoyl phosphate.
Protein Details
• Acetyl-coenzyme A synthetase
General function:
Involved in acetate-CoA ligase activity
Specific function:
Enables the cell to use acetate during aerobic growth to generate energy via the TCA cycle, and biosynthetic compounds via the glyoxylate shunt. Acetylates CheY, the response regulator involved in flagellar movement and chemotaxis
Gene Name:
acs
Locus Tag:
PA0887
Molecular weight:
71.8 kDa
Reactions
ATP + acetate + CoA = AMP + diphosphate + acetyl-CoA.
Protein Details
• Aldehyde dehydrogenase B
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADP-dependent oxidation of diverse aldehydes such as chloroacetaldehyde, acetaldehyde, propionaldehyde, benzaldehyde, mafosfamide, 4- hydroperoxycyclophosphamide. Its preferred substrates are acetaldehyde and chloroacetaldehyde
Gene Name:
aldB
Locus Tag:
PA1984
Molecular weight:
54.9 kDa

Transporters

Protein Details
• Sodium/proline symporter
General function:
Involved in proline:sodium symporter activity
Specific function:
Catalyzes the sodium-dependent uptake of extracellular L-proline. This protein is also capable of using lithium as the transport cation. Also catalyzes the uptake of propionate
Gene Name:
putP
Locus Tag:
PA0783
Molecular weight:
54.4 kDa