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Bovine Metabolome Database



Showing metabocard for Butyric acid (BMDB00039)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:39
Accession Number BMDB00039
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) 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.
Synonyms
  1. 1-Butyrate
  2. 1-Butyric acid
  3. 1-Propanecarboxylate
  4. 1-Propanecarboxylic acid
  5. 1-butanoate
  6. 1-butanoic acid
  7. Butanate
  8. Butanic acid
  9. Butanoate
  10. Butanoic acid
  11. Buttersaeure
  12. Butyrate
  13. Ethylacetate
  14. Ethylacetic acid
  15. Honey robber
  16. Kyselina maselna
  17. Propanecarboxylate
  18. Propanecarboxylic acid
  19. Propylformate
  20. Propylformic acid
  21. butyric acid
  22. n-Butanoate
  23. n-Butanoic acid
  24. n-Butyrate
  25. n-Butyric acid
Chemical IUPAC Name Butanoic acid
Chemical Formula C4H8O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Fatty Acids
Sub Class
  • Short chain fatty acids
Family
  • Microbial_Metabolite
Species
  • carboxylic acid
Biofunction
  • Energy source; DNA component
Application
Source
  • Endogenous
Average Molecular Weight 88.105
Monoisotopic Molecular Weight 88.052429
Isomeric SMILES CCCC(O)=O
Canonical SMILES CCCC(O)=O
KEGG Compound ID C00246 Link Image
BioCyc ID Not Available
BiGG ID 34376 Link Image
Wikipedia Link Butyric acid Link Image
METLIN ID 107 Link Image
PubChem Compound 264 Link Image
PubChem Substance 3545 Link Image
ChEBI ID 30772 Link Image
CAS Registry Number 107-92-6
InChI Identifier InChI=1/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
Synthesis Reference Shan, Zhiping. Preparation of butyric acid by hydrogenation of maleic anhydride. U.S. Pat. Appl. Publ. (2008), 6pp.
Melting Point (Experimental) -5.7 oC
Experimental Water Solubility 60.0 mg/mL [HEMPHILL,L & SWANSON,WS (1964)] Source: PhysProp
Predicted Water Solubility 239.00002 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Liquid
Experimental LogP/Hydrophobicity 0.79 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 0.78 [Predicted by ALOGPS]; 0.7 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
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Experimental 13C NMR Spectrum Download Spectrum
Download FID (Bruker)
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Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
  • mitochondria
Biofluid Location
  • Rumen
Tissue Location
Tissue References
Fibroblasts
Intestine
Kidney
Large Intestine
Muscle
Neuron
Prostate
Concentrations (Normal)
Biofluid Breast_Milk
Value 54 +/- 17 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 2% milk
References
Biofluid Breast_Milk
Value 28 +/- 2 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in skim milk
References
Biofluid Breast_Milk
Value 41 +/- 5 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 1% milk
References
Biofluid Breast_Milk
Value 58 +/- 18 uM
Age N/A
Sex N/A
Condition Normal
Comments Quantified by NMR in 3.25% milk
References
Biofluid Breast_Milk
Value 17138.641 +/- 2724.0225 uM
Age NA
Sex NA
Condition Normal
Comments The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples.
References
Biofluid Breast_Milk
Value 16798.139 +/- 2837.523 uM
Age NA
Sex NA
Condition Normal
Comments The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples.
References
Biofluid Breast_Milk
Value 9013.585 uM
Age NA
Sex NA
Condition Normal
Comments Cow reduced fat milk (2% fat) with added vitamin A
References
Biofluid Breast_Milk
Value 2809.429 uM
Age NA
Sex NA
Condition Normal
Comments Cow reduced fat milk (1% fat) with added vitamin A
References
Biofluid Breast_Milk
Value 470.129 uM
Age NA
Sex NA
Condition Normal
Comments Cow skim milk with added vitamin A
References
Biofluid Breast_Milk
Value 8779.466 uM
Age NA
Sex NA
Condition Normal
Comments Cow whole milk (3.25% fat)
References
Biofluid Breast_Milk
Value 31780.262 +/- 12485.103 uM
Age NA
Sex NA
Condition Normal
Comments Raw milk
References
Biofluid Rumen
Value 9386.24 +/- 1366.99 uM
Age N/A
Sex N/A
Condition Normal
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal)
Biofluid Rumen
Value 15131.93 +/- 2863.24 uM
Age N/A
Sex N/A
Condition Rumen acidosis
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names
  • Butyrate Metabolism
HMDB Pathways
Name Butyrate Metabolism
Image Show Link Image
KEGG Pathways
Name Butyrate Metabolism
Image Show Link Image
SimCell Pathways
Name Butyrate Metabolism
Image Show Link Image
Graph
SBML
General References
  1. Wikipedia Link Image