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Bovine Rumen Metabolome Database



Showing metabocard for Isobutyric acid (RMDB01873)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2006-02-23 12:29:19
Update Date 2009-10-28 13:28:25
Accession Number RMDB01873
Common Name Isobutyric acid
Description Isobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell. Small amount of isobutyrate is generated via microbial (gut) metabolism. Small amounts may also be found in certain foods or fermented beverages. There is anosmia (genetic inability to smell) for the odor of isobutyric acid with a frequency of about 2.5%. (OMIM 207000). Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents. Isobutyric acid can affect people if breathed in and may be absorbed through the skin. Contact can irritate and burn the skin and eyes. Breathing Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath.
Synonyms
  1. 2-Methylpropanoate
  2. 2-Methylpropanoic acid
  3. 2-Methylpropionate
  4. 2-Methylpropionic acid
  5. Dimethylacetate
  6. Dimethylacetic acid
  7. Isobutanoate
  8. Isobutanoic acid
  9. Isobutyrate
  10. Isopropylformate
  11. Isopropylformic acid
  12. a-Methylpropanoate
  13. a-Methylpropanoic acid
  14. a-Methylpropionate
  15. a-Methylpropionic acid
  16. i-Butyrate
  17. i-Butyric acid
  18. iso-Butyrate
  19. iso-Butyric acid
  20. isobutyric acid
  21. alpha-Methylpropanoate
  22. alpha-Methylpropanoic acid
  23. alpha-Methylpropionate
  24. alpha-Methylpropionic acid
Chemical IUPAC Name isobutyric 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
Application
Source
  • Endogenous
Average Molecular Weight 88.105
Monoisotopic Molecular Weight 88.052429
Isomeric SMILES CC(C)C(O)=O
Canonical SMILES CC(C)C(O)=O
KEGG Compound ID C02632 Link Image
BioCyc ID ISOBUTANOATE Link Image
BiGG ID Not Available
Wikipedia Link Isobutyric acid Link Image
METLIN ID 106 Link Image
PubChem Compound 6590 Link Image
PubChem Substance 10328650 Link Image
ChEBI ID 16135 Link Image
CAS Registry Number 79-31-2
InChI Identifier InChI=1/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
Synthesis Reference Wang, Hengxiu; Chen, Weibin; Zhao, Dehua; Zhang, Jianbin. Preparation of isobutyric acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 5 pp.
Melting Point (Experimental) -46 oC
Experimental Water Solubility 167 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 197.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Liquid
Experimental LogP/Hydrophobicity 0.94 [SANGSTER (1993)] Source: PhysProp
Predicted LogP/Hydrophobicity 0.78 [Predicted by ALOGPS]; 0.5 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
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Medium Energy
Download File
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 590 +/- 50 uM
Age N/A
Sex Both
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
Biofluid Rumen
Value 1429.07 +/- 228.2 uM
Age 4-5 years old
Sex Female (lactating)
Condition Normal (0% barley grain in dry matter (DM) basis)
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 1281.5 +/- 2.1 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Burim N. Ametaj, Qendrim Zebeli, Fozia Saleem, Nikolaos Psychogios, Michael J. Lewis, Suzanna M. Dunn, Jianguo Xia and David S. Wishart Metabolomics 2010;6(4):583-594
Concentrations (Abnormal)
Biofluid Rumen
Value 1450 +/- 180 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 1670 +/- 530 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 1815 +/- 194 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image