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Human Metabolome Database Version 3.5

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Showing metabocard for Isocaproic acid (HMDB00689)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:06 -0700
HMDB ID HMDB00689
Secondary Accession Numbers None
Metabolite Identification
Common Name Isocaproic acid
Description Isocaproic acid, a metabolite of 20 alpha-hydroxycholesterol (PMID 14446007 Link_out) and is an important metabolite in early placentas enabling the convertion from cholesterol to pregnenolone to Dehydroepiandrosterone (DHEA) (PMID 11972299 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 4,4-Dimethylbutanoate
  2. 4,4-Dimethylbutanoic acid
  3. 4-Methyl-N-valerate
  4. 4-Methyl-N-valeric acid
  5. 4-Methyl-pentanoate
  6. 4-Methyl-pentanoic acid
  7. 4-Methyl-Valerate
  8. 4-Methyl-Valeric acid
  9. 4-Methylpentanoate
  10. 4-Methylpentanoic acid
  11. 4-Methylvalerate
  12. 4-Methylvaleric acid
  13. Isobutylacetate
  14. Isobutylacetic acid
  15. Isocaproate
  16. Isocaproic acid
  17. Isohexanoate
  18. Isohexanoic acid
  19. Isohexoate
  20. Isohexoic acid
Chemical Formula C6H12O2
Average Molecular Weight 116.1583
Monoisotopic Molecular Weight 116.083729628
IUPAC Name 4-methylpentanoic acid
Traditional IUPAC Name 4-methyl valeric acid
CAS Registry Number 646-07-1
SMILES CC(C)CCC(O)=O
InChI Identifier InChI=1S/C6H12O2/c1-5(2)3-4-6(7)8/h5H,3-4H2,1-2H3,(H,7,8)
InChI Key FGKJLKRYENPLQH-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Branched Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Branched fatty acids(Lipidmaps)
  • Organic Compounds
Substituents
  • Carboxylic Acid
Direct Parent Branched Fatty Acids
Ontology
Status Detected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -33 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 12.9 g/L ALOGPS
LogP 1.72 ALOGPS
LogP 1.65 ChemAxon
LogS -0.96 ALOGPS
pKa (strongest acidic) 5.09 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 31.02 ChemAxon
Polarizability 13.07 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 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
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and not Quantified
Article_icon
Not Applicable Not Available Male Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB03993 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB008206
KNApSAcK ID Not Available
Chemspider ID 12067 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00689 Link_out
Metagene Link HMDB00689 Link_out
METLIN ID 4191 Link_out
PubChem Compound 12587 Link_out
PDB ID 4MV Link_out
ChEBI ID Not Available
References
Synthesis Reference Shimizu, K.; Dorfman, Ralph I.; Gut, Marcel. Isocaproic acid, a metabolite of 20a-hydroxycholesterol. Journal of Biological Chemistry (1960), 235 PC25.
Material Safety Data Sheet (MSDS) Not Available
General References Not Available