Human Metabolome Database Version 3.5

Showing metabocard for Butyric acid (HMDB00039)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:24:36 -0600
HMDB ID HMDB00039
Secondary Accession Numbers None
Metabolite Identification
Common Name Butyric acid
Description Butyric acid, a four-carbon fatty acid, is formed in the human colon by bacterial fermentation of carbohydrates (including dietary fiber), and putatively suppresses colorectal cancer (CRC). Butyrate has diverse and apparently paradoxical effects on cellular proliferation, apoptosis and differentiation that may be either pro-neoplastic or anti-neoplastic, depending upon factors such as the level of exposure, availability of other metabolic substrate and the intracellular milieu. In humans, the relationship between luminal butyrate exposure and CRC has been examined only indirectly in case-control studies, by measuring fecal butyrate concentrations, although this may not accurately reflect effective butyrate exposure during carcinogenesis. Perhaps not surprisingly, results of these investigations have been mutually contradictory. The direct effect of butyrate on tumorigenesis has been assessed in a no. of in vivo animal models, which have also yielded conflicting results. In part, this may be explained by methodology: differences in the amount and route of butyrate administration, which are likely to significantly influence delivery of butyrate to the distal colon. (PMID: 16460475 Link_out) Butyric acid is a carboxylic acid found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. Interestingly, low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes. As a consequence, they find use as food and perfume additives. Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Butanoate
  2. 1-Butanoic acid
  3. 1-Butyrate
  4. 1-Butyric acid
  5. 1-Propanecarboxylate
  6. 1-Propanecarboxylic acid
  7. Butanate
  8. Butanic acid
  9. Butanoate
  10. Butanoic acid
  11. Buttersaeure
  12. Butyrate
  13. Butyric acid
  14. Ethylacetate
  15. Ethylacetic acid
  16. Honey robber
  17. Kyselina maselna
  18. N-Butanoate
  19. N-Butanoic acid
  20. N-Butyrate
  21. N-Butyric acid
  22. Propanecarboxylate
  23. Propanecarboxylic acid
  24. Propylformate
  25. Propylformic acid
Chemical Formula C4H8O2
Average Molecular Weight 88.1051
Monoisotopic Molecular Weight 88.0524295
IUPAC Name butanoic acid
Traditional IUPAC Name butanoic acid
CAS Registry Number 107-92-6
SMILES CCCC(O)=O
InChI Identifier InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
InChI Key FERIUCNNQQJTOY-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Straight Chain Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Saturated fatty acids(KEGG)
  • Straight chain fatty acids(KEGG)
  • Straight chain fatty acids(Lipidmaps)
  • short-chain fatty acid(ChEBI)
  • straight-chain saturated fatty acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct Parent Straight Chain Fatty Acids
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
  • Microbial
Biofunction
  • Cell signaling
  • DNA component
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -5.7 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 60.0 mg/mL Not Available
LogP 0.79 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 239 g/L ALOGPS
LogP 0.78 ALOGPS
LogP 0.92 ChemAxon
LogS 0.43 ALOGPS
pKa (strongest acidic) 4.91 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 21.87 ChemAxon
Polarizability 9.23 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
13C 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-7M)
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
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Fibroblasts
  • Intestine
  • Neuron
  • Kidney
  • Prostate
  • Large Intestine
Pathways
Name SMPDB Link KEGG Link
Butyrate Metabolism SMP00073 map00650 Link_out
Fatty Acid Biosynthesis SMP00456 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.0 (0.3- 1.5) uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
1.4 (0-2.8) uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Saliva Detected and Quantified
1470 (0.00-2940) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.6 (0.5-4.0) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
0.131 +/- 0.013 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
3.2 (0.0-6.4) umol/mmol creatinine Infant (0-1 year old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
42.0 (21.0-81.0) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified 0.18 +/- 0.044 umol/mmol creatinine Adult (>18 years old) Both AIDS
Associated Disorders and Diseases
Disease References
AIDS
  • Stein TP, Koerner B, Schluter MD, Leskiw MJ, Gaprindachvilli T, Richards EW, Cope FO, Condolucci D: Weight loss, the gut and the inflammatory response in aids patients. Cytokine. 1997 Feb;9(2):143-7. Pubmed: 9071566 Link_out
      Associated OMIM IDs None
      DrugBank ID DB03568 Link_out
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB012062
      KNApSAcK ID C00001180 Link_out
      Chemspider ID 259 Link_out
      KEGG Compound ID C00246 Link_out
      BioCyc ID Not Available
      BiGG ID 34376 Link_out
      Wikipedia Link Butyric acid Link_out
      NuGOwiki Link HMDB00039 Link_out
      Metagene Link HMDB00039 Link_out
      METLIN ID 107 Link_out
      PubChem Compound 264 Link_out
      PDB ID BUA Link_out
      ChEBI ID 30772 Link_out
      References
      Synthesis Reference Shan, Zhiping. Preparation of butyric acid by hydrogenation of maleic anhydride. U.S. Pat. Appl. Publ. (2008), 6pp.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. McMillan L, Butcher SK, Pongracz J, Lord JM: Opposing effects of butyrate and bile acids on apoptosis of human colon adenoma cells: differential activation of PKC and MAP kinases. Br J Cancer. 2003 Mar 10;88(5):748-53. Pubmed: 12618885 Link_out
      2. Bauer G: Induction of Epstein-Barr virus early antigens by corticosteroids: inhibition by TPA and retinoic acid. Int J Cancer. 1983 Mar 15;31(3):291-5. Pubmed: 6826253 Link_out
      3. 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
      4. McIntosh GH, Noakes M, Royle PJ, Foster PR: Whole-grain rye and wheat foods and markers of bowel health in overweight middle-aged men. Am J Clin Nutr. 2003 Apr;77(4):967-74. Pubmed: 12663299 Link_out
      5. Schwiertz A, Lehmann U, Jacobasch G, Blaut M: Influence of resistant starch on the SCFA production and cell counts of butyrate-producing Eubacterium spp. in the human intestine. J Appl Microbiol. 2002;93(1):157-62. Pubmed: 12067385 Link_out
      6. Bauer G, Hofler P, Simon M: Epstein-Barr virus induction by a serum factor. Characterization of the purified factor and the mechanism of its activation. J Biol Chem. 1982 Oct 10;257(19):11411-5. Pubmed: 6288683 Link_out
      7. Jin SE, Ban E, Kim YB, Kim CK: Development of HPLC method for the determination of levosulpiride in human plasma. J Pharm Biomed Anal. 2004 Jun 29;35(4):929-36. Pubmed: 15193738 Link_out
      8. Welters CF, Heineman E, Thunnissen FB, van den Bogaard AE, Soeters PB, Baeten CG: Effect of dietary inulin supplementation on inflammation of pouch mucosa in patients with an ileal pouch-anal anastomosis. Dis Colon Rectum. 2002 May;45(5):621-7. Pubmed: 12004211 Link_out
      9. Kurita-Ochiai T, Seto S, Ochiai K: Role of cell-cell communication in inhibiting butyric acid-induced T-cell apoptosis. Infect Immun. 2004 Oct;72(10):5947-54. Pubmed: 15385498 Link_out
      10. Cruz HG, Ivanova T, Lunn ML, Stoffel M, Slesinger PA, Luscher C: Bi-directional effects of GABA(B) receptor agonists on the mesolimbic dopamine system. Nat Neurosci. 2004 Feb;7(2):153-9. Epub 2004 Jan 25. Pubmed: 14745451 Link_out
      11. Yonemura K, Sairenji T, Hinuma Y: Inhibitory effect of 1-beta-D-arabinofuranosylthymine on synthesis of Epstein-Barr virus. Microbiol Immunol. 1981;25(6):557-63. Pubmed: 6268944 Link_out
      12. Teichert J, Tuemmers T, Achenbach H, Preiss C, Hermann R, Ruus P, Preiss R: Pharmacokinetics of alpha-lipoic acid in subjects with severe kidney damage and end-stage renal disease. J Clin Pharmacol. 2005 Mar;45(3):313-28. Pubmed: 15703366 Link_out
      13. Rephaeli A, Blank-Porat D, Tarasenko N, Entin-Meer M, Levovich I, Cutts SM, Phillips DR, Malik Z, Nudelman A: In vivo and in vitro antitumor activity of butyroyloxymethyl-diethyl phosphate (AN-7), a histone deacetylase inhibitor, in human prostate cancer. Int J Cancer. 2005 Aug 20;116(2):226-35. Pubmed: 15800932 Link_out
      14. Kurita-Ochiai T, Ochiai K, Suzuki N, Otsuka K, Fukushima K: Human gingival fibroblasts rescue butyric acid-induced T-cell apoptosis. Infect Immun. 2002 May;70(5):2361-7. Pubmed: 11953371 Link_out
      15. Jacobasch G, Jacobasch KH: [Molecular etiology of colorectal carcinogenesis, clinical manifestations and therapy] Z Arztl Fortbild Qualitatssich. 1997 Mar;91(2):125-33. Pubmed: 9244653 Link_out
      16. Velazquez OC, Lederer HM, Rombeau JL: Butyrate and the colonocyte. Production, absorption, metabolism, and therapeutic implications. Adv Exp Med Biol. 1997;427:123-34. Pubmed: 9361838 Link_out
      17. Kawanishi M, Ito Y: Effect of short-chain fatty acids on Epstein-Barr virus early and viral capsid antigen induction in P3HR-1 cells. Cancer Lett. 1980 Dec;11(2):129-32. Pubmed: 6257378 Link_out
      18. Stein TP, Koerner B, Schluter MD, Leskiw MJ, Gaprindachvilli T, Richards EW, Cope FO, Condolucci D: Weight loss, the gut and the inflammatory response in aids patients. Cytokine. 1997 Feb;9(2):143-7. Pubmed: 9071566 Link_out
      19. Sengupta S, Muir JG, Gibson PR: Does butyrate protect from colorectal cancer? J Gastroenterol Hepatol. 2006 Jan;21(1 Pt 2):209-18. Pubmed: 16460475 Link_out

      Enzymes
      Name: Cholinesterase
      Reactions: Not Available
      Gene Name: BCHE
      Uniprot ID: P06276 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Tumor necrosis factor
      Reactions: Not Available
      Gene Name: TNF
      Uniprot ID: P01375 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Peroxisome proliferator-activated receptor gamma
      Reactions: Not Available
      Gene Name: PPARG
      Uniprot ID: P37231 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Histone deacetylase 4
      Reactions: Not Available
      Gene Name: HDAC4
      Uniprot ID: P56524 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Histone deacetylase 9
      Reactions: Not Available
      Gene Name: HDAC9
      Uniprot ID: Q9UKV0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acyl-coenzyme A synthetase ACSM1, mitochondrial
      Reactions:
      Adenosine triphosphate + Butyric acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Butyryl-CoA details
      Gene Name: ACSM1
      Uniprot ID: Q08AH1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acyl-coenzyme A synthetase ACSM6, mitochondrial
      Reactions: Not Available
      Gene Name: ACSM6
      Uniprot ID: Q6P461 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acyl-coenzyme A synthetase ACSM2A, mitochondrial
      Reactions:
      Adenosine triphosphate + Butyric acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Butyryl-CoA details
      Gene Name: ACSM2A
      Uniprot ID: Q08AH3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acyl-coenzyme A synthetase ACSM2B, mitochondrial
      Reactions:
      Adenosine triphosphate + Butyric acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Butyryl-CoA details
      Gene Name: ACSM2B
      Uniprot ID: Q68CK6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acyl-coenzyme A synthetase ACSM3, mitochondrial
      Reactions:
      Adenosine triphosphate + Butyric acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Butyryl-CoA details
      Gene Name: ACSM3
      Uniprot ID: Q53FZ2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acyl-coenzyme A synthetase ACSM5, mitochondrial
      Reactions:
      Adenosine triphosphate + Butyric acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Butyryl-CoA details
      Gene Name: ACSM5
      Uniprot ID: Q6NUN0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Histone deacetylase 2
      Reactions: Not Available
      Gene Name: HDAC2
      Uniprot ID: Q92769 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Histone deacetylase 3
      Reactions: Not Available
      Gene Name: HDAC3
      Uniprot ID: O15379 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Histone deacetylase 5
      Reactions: Not Available
      Gene Name: HDAC5
      Uniprot ID: Q9UQL6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acyl-coenzyme A synthetase ACSM4, mitochondrial
      Reactions:
      Adenosine triphosphate + Butyric acid + Coenzyme A unknown Adenosine monophosphate + Pyrophosphate + Butyryl-CoA details
      Gene Name: ACSM4
      Uniprot ID: P0C7M7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Transporters
      Name: Monocarboxylate transporter 1
      Reactions: Not Available
      Gene Name: SLC16A1
      Uniprot ID: P53985 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA