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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:24:36 UTC
HMDB IDHMDB00039
Secondary Accession NumbersNone
Metabolite Identification
Common NameButyric acid
DescriptionButyric 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 ) 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
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 FormulaC4H8O2
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
IUPAC Namebutanoic acid
Traditional IUPAC Namebutanoic acid
CAS Registry Number107-92-6
SMILES
CCCC(O)=O
InChI Identifier
InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
InChI KeyFERIUCNNQQJTOY-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acids and Conjugates
Sub ClassStraight 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 ParentStraight Chain Fatty Acids
Ontology
StatusDetected 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
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-5.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility60.0 mg/mLNot Available
LogP0.79HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility239 g/LALOGPS
logP0.78ALOGPS
logP0.92ChemAxon
logS0.43ALOGPS
pKa (Strongest Acidic)4.91ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity21.87ChemAxon
Polarizability9.23ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Kidney
  • Large Intestine
  • Muscle
  • Neuron
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Butyrate MetabolismSMP00073map00650
Fatty Acid BiosynthesisSMP00456Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.0 (0.3- 1.5) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified1.4 (0-2.8) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
SalivaDetected and Quantified1470 (0.00-2940) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.6 (0.5-4.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.131 +/- 0.013 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.2 (0.0-6.4) umol/mmol creatinineInfant (0-1 year old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified42.0 (21.0-81.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.18 +/- 0.044 umol/mmol creatinineAdult (>18 years old)BothAIDS details
Associated Disorders and Diseases
Disease References
AIDS
  1. 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
Associated OMIM IDsNone
DrugBank IDDB03568
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012062
KNApSAcK IDC00001180
Chemspider ID259
KEGG Compound IDC00246
BioCyc IDNot Available
BiGG ID34376
Wikipedia LinkButyric acid
NuGOwiki LinkHMDB00039
Metagene LinkHMDB00039
METLIN ID107
PubChem Compound264
PDB IDBUA
ChEBI ID30772
References
Synthesis ReferenceShan, 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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
General function:
Involved in tumor necrosis factor receptor binding
Specific function:
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation
Gene Name:
TNF
Uniprot ID:
P01375
Molecular weight:
25644.1
References
  1. Fukae J, Amasaki Y, Yamashita Y, Bohgaki T, Yasuda S, Jodo S, Atsumi T, Koike T: Butyrate suppresses tumor necrosis factor alpha production by regulating specific messenger RNA degradation mediated through a cis-acting AU-rich element. Arthritis Rheum. 2005 Sep;52(9):2697-707. Pubmed: 16142751
General function:
Involved in DNA binding
Specific function:
Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular weight:
57619.6
References
  1. Schwab M, Reynders V, Ulrich S, Zahn N, Stein J, Schroder O: PPARgamma is a key target of butyrate-induced caspase-3 activation in the colorectal cancer cell line Caco-2. Apoptosis. 2006 Oct;11(10):1801-11. Pubmed: 16927016
General function:
Involved in histone deacetylase activity
Specific function:
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an important role in transcriptional regulation, cell cycle progression and developmental events. Histone deacetylases act via the formation of large multiprotein complexes. Involved in muscle maturation via its interaction with the myocyte enhancer factors such as MEF2A, MEF2C and MEF2D
Gene Name:
HDAC4
Uniprot ID:
P56524
Molecular weight:
119038.9
References
  1. Ishihara K, Takahashi A, Kaneko M, Sugeno H, Hirasawa N, Hong J, Zee O, Ohuchi K: Differentiation of eosinophilic leukemia EoL-1 cells into eosinophils induced by histone deacetylase inhibitors. Life Sci. 2007 Mar 6;80(13):1213-20. Epub 2007 Jan 11. Pubmed: 17258775
General function:
Involved in histone deacetylase activity
Specific function:
Isoform 3 lacks active site residues and therefore is catalytically inactive. Represses MEF2-dependent transcription by recruiting HDAC1 and/or HDAC3. Seems to inhibit skeletal myogenesis and to be involved in heart development. Protects neurons from apoptosis, both by inhibiting JUN phosphorylation by MAPK10 and by repressing JUN transcription via HDAC1 recruitment to JUN promoter
Gene Name:
HDAC9
Uniprot ID:
Q9UKV0
Molecular weight:
111296.3
References
  1. Ishihara K, Takahashi A, Kaneko M, Sugeno H, Hirasawa N, Hong J, Zee O, Ohuchi K: Differentiation of eosinophilic leukemia EoL-1 cells into eosinophils induced by histone deacetylase inhibitors. Life Sci. 2007 Mar 6;80(13):1213-20. Epub 2007 Jan 11. Pubmed: 17258775
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro). Functions as GTP-dependent lipoate-activating enzyme that generates the substrate for lipoyltransferase (By similarity).
Gene Name:
ACSM1
Uniprot ID:
Q08AH1
Molecular weight:
65272.74
Reactions
Adenosine triphosphate + Butyric acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Butyryl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ACSM6
Uniprot ID:
Q6P461
Molecular weight:
53584.545
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM2A
Uniprot ID:
Q08AH3
Molecular weight:
64223.7
Reactions
Adenosine triphosphate + Butyric acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Butyryl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro).
Gene Name:
ACSM2B
Uniprot ID:
Q68CK6
Molecular weight:
64270.78
Reactions
Adenosine triphosphate + Butyric acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Butyryl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM3
Uniprot ID:
Q53FZ2
Molecular weight:
66152.235
Reactions
Adenosine triphosphate + Butyric acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Butyryl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM5
Uniprot ID:
Q6NUN0
Molecular weight:
64759.55
Reactions
Adenosine triphosphate + Butyric acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Butyryl-CoAdetails
General function:
Involved in histone deacetylase activity
Specific function:
Forms transcriptional repressor complexes by associating with MAD, SIN3, YY1 and N-COR. Interacts in the late S-phase of DNA-replication with DNMT1 in the other transcriptional repressor complex composed of DNMT1, DMAP1, PCNA, CAF1. Deacetylates TSHZ3 and regulates its transcriptional repressor activity
Gene Name:
HDAC2
Uniprot ID:
Q92769
Molecular weight:
55363.9
References
  1. Ishihara K, Takahashi A, Kaneko M, Sugeno H, Hirasawa N, Hong J, Zee O, Ohuchi K: Differentiation of eosinophilic leukemia EoL-1 cells into eosinophils induced by histone deacetylase inhibitors. Life Sci. 2007 Mar 6;80(13):1213-20. Epub 2007 Jan 11. Pubmed: 17258775
General function:
Involved in histone deacetylase activity
Specific function:
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an important role in transcriptional regulation, cell cycle progression and developmental events. Histone deacetylases act via the formation of large multiprotein complexes. Probably participates in the regulation of transcription through its binding to the zinc-finger transcription factor YY1; increases YY1 repression activity. Required to repress transcription of the POU1F1 transcription factor
Gene Name:
HDAC3
Uniprot ID:
O15379
Molecular weight:
48847.4
References
  1. Ishihara K, Takahashi A, Kaneko M, Sugeno H, Hirasawa N, Hong J, Zee O, Ohuchi K: Differentiation of eosinophilic leukemia EoL-1 cells into eosinophils induced by histone deacetylase inhibitors. Life Sci. 2007 Mar 6;80(13):1213-20. Epub 2007 Jan 11. Pubmed: 17258775
General function:
Involved in histone deacetylase activity
Specific function:
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an important role in transcriptional regulation, cell cycle progression and developmental events. Histone deacetylases act via the formation of large multiprotein complexes. Involved in muscle maturation by repressing transcription of myocyte enhancer MEF2C. During muscle differentiation, it shuttles into the cytoplasm, allowing the expression of myocyte enhancer factors
Gene Name:
HDAC5
Uniprot ID:
Q9UQL6
Molecular weight:
121976.9
References
  1. Ishihara K, Takahashi A, Kaneko M, Sugeno H, Hirasawa N, Hong J, Zee O, Ohuchi K: Differentiation of eosinophilic leukemia EoL-1 cells into eosinophils induced by histone deacetylase inhibitors. Life Sci. 2007 Mar 6;80(13):1213-20. Epub 2007 Jan 11. Pubmed: 17258775
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM4
Uniprot ID:
P0C7M7
Molecular weight:
65702.225
Reactions
Adenosine triphosphate + Butyric acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Butyryl-CoAdetails

Transporters

General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
SLC16A1
Uniprot ID:
P53985
Molecular weight:
53957.7
References
  1. Borthakur A, Saksena S, Gill RK, Alrefai WA, Ramaswamy K, Dudeja PK: Regulation of monocarboxylate transporter 1 (MCT1) promoter by butyrate in human intestinal epithelial cells: involvement of NF-kappaB pathway. J Cell Biochem. 2008 Apr 1;103(5):1452-63. Pubmed: 17786924