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Human Metabolome Database Version 3.5

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Showing metabocard for Isobutyric acid (HMDB01873)

Record Information
Version 3.5
Creation Date 2006-02-23 05:29:19 -0700
Update Date 2013-02-08 17:10:54 -0700
HMDB ID HMDB01873
Secondary Accession Numbers
  • HMDB03151
Metabolite Identification
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 Link_out). 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Methylpropanoate
  2. 2-Methylpropanoic acid
  3. 2-Methylpropionate
  4. 2-Methylpropionic acid
  5. a-Methylpropanoate
  6. a-Methylpropanoic acid
  7. a-Methylpropionate
  8. a-Methylpropionic acid
  9. alpha-Methylpropanoate
  10. alpha-Methylpropanoic acid
  11. alpha-Methylpropionate
  12. alpha-Methylpropionic acid
  13. Dimethylacetate
  14. Dimethylacetic acid
  15. i-Butyrate
  16. i-Butyric acid
  17. Iso-Butyrate
  18. Iso-Butyric acid
  19. Isobutanoate
  20. Isobutanoic acid
  21. Isobutyrate
  22. Isobutyric acid
  23. Isopropylformate
  24. Isopropylformic acid
Chemical Formula C4H8O2
Average Molecular Weight 88.1051
Monoisotopic Molecular Weight 88.0524295
IUPAC Name 2-methylpropanoic acid
Traditional IUPAC Name isobutyric acid
CAS Registry Number 79-31-2
SMILES CC(C)C(O)=O
InChI Identifier InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
InChI Key KQNPFQTWMSNSAP-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
  • Branched fatty acids(Lipidmaps)
  • branched-chain saturated fatty acid(ChEBI)
  • methyl-branched fatty acid(ChEBI)
  • short-chain fatty acid(ChEBI)
Substituents
  • N/A
Direct Parent Carboxylic Acids
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -46 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 167 mg/mL at 20 °C Not Available
LogP 0.94 SANGSTER (1993)
Predicted Properties
Property Value Source
Water Solubility 197 g/L ALOGPS
LogP 0.78 ALOGPS
LogP 1.02 ChemAxon
LogS 0.35 ALOGPS
pKa (strongest acidic) 4.87 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 21.85 ChemAxon
Polarizability 9.1 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
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-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 Not Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Fibroblasts
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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2.3 (0.7-4.4) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1.8 (0-3.6) uM Adult (>18 years old) Both Normal Not Available
Saliva Detected and Quantified
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885.0 (10.0-1760.0) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
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2.82 umol/mmol creatinine Adult (>18 years old) Male Normal Based on one measurement
Urine Detected and Quantified
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15.0 (12.0-27.0) umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
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39.0 (9.0-122.0) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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3.5 (1.2-9.0) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Male Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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8.4 +/- 1.9 uM Adult (>18 years old) Not Specified Heart Transplant Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB02531 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB003277
KNApSAcK ID C00029462 Link_out
Chemspider ID 6341 Link_out
KEGG Compound ID C02632 Link_out
BioCyc ID ISOBUTANOATE Link_out
BiGG ID Not Available
Wikipedia Link Isobutyric acid Link_out
NuGOwiki Link HMDB01873 Link_out
Metagene Link HMDB01873 Link_out
METLIN ID 106 Link_out
PubChem Compound 6590 Link_out
PDB ID ALQ Link_out
ChEBI ID 16135 Link_out
References
Synthesis Reference Wang, Hengxiu; Chen, Weibin; Zhao, Dehua; Zhang, Jianbin. Preparation of isobutyric acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 5 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Mix KS, Coon CI, Rosen ED, Suh N, Sporn MB, Brinckerhoff CE: Peroxisome proliferator-activated receptor-gamma-independent repression of collagenase gene expression by 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid and prostaglandin 15-deoxy-delta(12,14) J2: a role for Smad signaling. Mol Pharmacol. 2004 Feb;65(2):309-18. Pubmed: 14742672 Link_out
  2. 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
  3. Faed EM, McQueen EG: Separation of two conjugates of clofibric acid (CPIB) found in the urine of subjects taking clofibrate. Clin Exp Pharmacol Physiol. 1978 Mar-Apr;5(2):195-8. Pubmed: 648038 Link_out
  4. Hoverstad T, Fausa O, Bjorneklett A, Bohmer T: Short-chain fatty acids in the normal human feces. Scand J Gastroenterol. 1984 May;19(3):375-81. Pubmed: 6740214 Link_out