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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:12 UTC
HMDB IDHMDB00689
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsocaproic acid
DescriptionIsocaproic acid, a metabolite of 20 alpha-hydroxycholesterol (PMID 14446007 ) and is an important metabolite in early placentas enabling the convertion from cholesterol to pregnenolone to Dehydroepiandrosterone (DHEA) (PMID 11972299 ).
Structure
Thumb
Synonyms
ValueSource
4,4-Dimethylbutanoic acidChEBI
4-Methyl-N-valeric acidChEBI
4-Methyl-pentanoic acidChEBI
4-Methyl-valeric acidChEBI
4-Methylvaleric acidChEBI
Isobutylacetic acidChEBI
Isohexanoic acidChEBI
Isohexoic acidChEBI
4,4-DimethylbutanoateGenerator
IsocaproateGenerator
4-Methyl-N-valerateGenerator
4-Methyl-pentanoateGenerator
4-Methyl-valerateGenerator
4-MethylvalerateGenerator
IsobutylacetateGenerator
IsohexanoateGenerator
IsohexoateGenerator
4-MethylpentanoateHMDB
4-Methylpentanoic acidHMDB
Chemical FormulaC6H12O2
Average Molecular Weight116.1583
Monoisotopic Molecular Weight116.083729628
IUPAC Name4-methylpentanoic acid
Traditional Nameisocaproate
CAS Registry Number646-07-1
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 KeyInChIKey=FGKJLKRYENPLQH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and 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
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-33 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.9 mg/mLALOGPS
logP1.72ALOGPS
logP1.65ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)5.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.02 m3·mol-1ChemAxon
Polarizability13.06 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014j-6900000000-cb7997a5c6ca2f6418c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00gi-9100000000-da8f07a6e124535385f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001d-7900000000-d997ac31e14c8967a633View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0abc-9000000000-9da80434be2ce0d86913View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-f28fa3474851e17f83b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-6e23bff66db2ce8e669aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03di-4900000000-853711a3867735db4fa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9200000000-a87d3af0796b3929b585View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-9100000000-0dd3655055a4bd052af4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-5a494f4ea95bbce2ac3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-9419bcb9bb04937d3006View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-9400000000-d7efbb09535c4b1344f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-a61c06d9d6e46707a0a0View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0abc-9000000000-a381f69e01ac46730bd4View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified20.489 +/- 11.536 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified1695.961 +/- 581.104 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0 - 14.59 ppmChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected and Quantified43.65 +/- 44.98 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableMaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected and Quantified0 - 3.93 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03993
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008206
KNApSAcK IDNot Available
Chemspider ID12067
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00689
Metagene LinkHMDB00689
METLIN ID4191
PubChem Compound12587
PDB ID4MV
ChEBI IDNot Available
References
Synthesis ReferenceShimizu, 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
  1. SHIMIZU K, DORFMAN RI, GUT M: Isocaproic acid, a metabolite of 20 alpha-hydroxycholesterol. J Biol Chem. 1960 Jun;235:PC25. [14446007 ]
  2. Loganath A, Peh KL, Wong PC: Evidence for the biosynthesis of DHEA from cholesterol by first-trimester human placental tissue: source of androgens. Horm Metab Res. 2002 Mar;34(3):116-20. [11972299 ]