Human Metabolome Database Version 3.5

Showing metabocard for Propionic acid (HMDB00237)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:25:13 -0600
HMDB ID HMDB00237
Secondary Accession Numbers None
Metabolite Identification
Common Name Propionic acid
Description Propionic 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 humans 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 Link_out) 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 Link_out) 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Adofeed
  2. Antischim B
  3. Carboxyethane
  4. Ethanecarboxylate
  5. Ethanecarboxylic acid
  6. Ethylformate
  7. Ethylformic acid
  8. Luprosil
  9. Metacetonate
  10. Metacetonic acid
  11. Methylacetate
  12. Methylacetic acid
  13. MonoProp
  14. Propanate
  15. Propanoate
  16. Propanoic acid
  17. Propcorn
  18. Propionate
  19. Propkorn
  20. Prozoin
  21. Pseudoacetate
  22. Pseudoacetic acid
  23. Toxi-Check
Chemical Formula C3H6O2
Average Molecular Weight 74.0785
Monoisotopic Molecular Weight 74.036779436
IUPAC Name propanoic acid
Traditional IUPAC Name propanoic acid
CAS Registry Number 79-09-4
SMILES CCC(O)=O
InChI Identifier InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)
InChI Key XBDQKXXYIPTUBI-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Carboxylic Acids and Derivatives
Sub Class Carboxylic Acid Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Saturated fatty acids(KEGG)
  • Straight chain fatty acids(KEGG)
  • Straight chain fatty acids(Lipidmaps)
  • saturated fatty acid(ChEBI)
  • short-chain fatty acid(ChEBI)
Substituents
  • N/A
Direct Parent Carboxylic Acids
Ontology
Status Detected and Quantified
Origin
  • Food
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -20.7 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1000.0 mg/mL Not Available
LogP 0.33 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 352 g/L ALOGPS
LogP 0.31 ALOGPS
LogP 0.48 ChemAxon
LogS 0.68 ALOGPS
pKa (strongest acidic) 4.75 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 17.27 ChemAxon
Polarizability 7.25 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-6M)
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Fibroblasts
  • Intestine
  • Neuron
  • Testes
  • Epidermis
  • Brain
  • Adipose Tissue
  • Platelet
  • Stratum Corneum
Pathways
Name SMPDB Link KEGG Link
Propanoate Metabolism SMP00016 map00640 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.6 +/- 1.2 uM Children (1-13 year old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
0.9 +/- 1.2 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
2.8 +/- 3.2 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Saliva Detected and Quantified
1-586 uM Adult (>18 years old) Male Comment normal
Saliva Detected and Quantified
1-100 uM Adult (>18 years old) Male Comment normal
Saliva Detected and Quantified
6420 (5920-6920) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.96 +/- 2.76 umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
14.0 (11.4-18.3) umol/mmol creatinine Infant (0-1 year old) Both Normal
  • Geigy Scient...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 2.5 (0.00-5.00) uM Children (1-13 year old) Both Propionic acidemia
Associated Disorders and Diseases
Disease References
Propionic acidemia
      Associated OMIM IDs
      DrugBank ID DB03766 Link_out
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB008285
      KNApSAcK ID Not Available
      Chemspider ID 1005 Link_out
      KEGG Compound ID C00163 Link_out
      BioCyc ID PROPIONATE Link_out
      BiGG ID 34098 Link_out
      Wikipedia Link Propionic acid Link_out
      NuGOwiki Link HMDB00237 Link_out
      Metagene Link HMDB00237 Link_out
      METLIN ID 3215 Link_out
      PubChem Compound 1032 Link_out
      PDB ID PPI Link_out
      ChEBI ID 30768 Link_out
      References
      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)
      General References
      1. 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 Link_out
      2. 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 Link_out
      3. Lin SC, Bergles DE: Synaptic signaling between neurons and glia. Glia. 2004 Aug 15;47(3):290-8. Pubmed: 15252819 Link_out
      4. 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 Link_out
      5. 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 Link_out
      6. 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 Link_out
      7. 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 Link_out
      8. 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 Link_out
      9. 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 Link_out
      10. 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 Link_out
      11. 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 Link_out
      12. 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 Link_out
      13. 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 Link_out
      14. 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 Link_out
      15. 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 Link_out
      16. 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 Link_out
      17. 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 Link_out
      18. 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 Link_out
      19. Harrison PT: Propionic acid and the phenomenon of rodent forestomach tumorigenesis: a review. Food Chem Toxicol. 1992 Apr;30(4):333-40. Pubmed: 1628870 Link_out
      20. 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 Link_out
      21. 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 Link_out

      Enzymes
      Name: Acetyl-coenzyme A synthetase, cytoplasmic
      Reactions:
      Adenosine triphosphate + Propionic acid unknown Pyrophosphate + Propinol adenylate details
      Gene Name: ACSS2
      Uniprot ID: Q9NR19 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acetyl-coenzyme A synthetase 2-like, mitochondrial
      Reactions:
      Adenosine triphosphate + Propionic acid unknown Pyrophosphate + Propinol adenylate details
      Gene Name: ACSS1
      Uniprot ID: Q9NUB1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Gephyrin
      Reactions: Not Available
      Gene Name: GPHN
      Uniprot ID: Q9NQX3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: ACSS2 protein
      Reactions: Not Available
      Gene Name: ACSS2
      Uniprot ID: Q96FY7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acyl-CoA synthetase short-chain family member 3, mitochondrial
      Reactions:
      Adenosine triphosphate + Propionic acid unknown Pyrophosphate + Propinol adenylate details
      Gene Name: ACSS3
      Uniprot ID: Q9H6R3 Link_out
      Protein Sequence: FASTA