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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:32:08 UTC
Update Date2019-07-23 06:26:05 UTC
HMDB IDHMDB0038250
Secondary Accession Numbers
  • HMDB38250
Metabolite Identification
Common NameIsobornyl isovalerate
DescriptionIsobornyl isovalerate, also known as fema 2166 or gynoval, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Isobornyl isovalerate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863165
Synonyms
ValueSource
Isobornyl isovaleric acidGenerator
3-Methyl-(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl esterrel-butanoic acidHMDB
3-Methyl-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl esterexo-butanoic acidHMDB
FEMA 2166HMDB
GynovalHMDB
Isobornyl 3-methylbutanoateHMDB
Isovaleric acid, isobornyl ester (8ci)HMDB
(1S,2S,4S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl 3-methylbutanoic acidGenerator
Isobornyl isovalerateMeSH
Chemical FormulaC15H26O2
Average Molecular Weight238.3657
Monoisotopic Molecular Weight238.193280076
IUPAC Name(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 3-methylbutanoate
Traditional Name(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 3-methylbutanoate
CAS Registry Number7779-73-9
SMILES
CC(C)CC(=O)O[C@H]1C[C@@H]2CC[C@@]1(C)C2(C)C
InChI Identifier
InChI=1S/C15H26O2/c1-10(2)8-13(16)17-12-9-11-6-7-15(12,5)14(11,3)4/h10-12H,6-9H2,1-5H3/t11-,12-,15+/m0/s1
InChI KeyMPYYVGIJHREDBO-SLEUVZQESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Bornane monoterpenoid
  • Fatty acid ester
  • Fatty acyl
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0094 g/LALOGPS
logP4.47ALOGPS
logP3.86ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.24 m³·mol⁻¹ChemAxon
Polarizability28.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6910000000-70789f87cdef00f6d884Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4590000000-62c3d63ca1e872b836c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-9800000000-f6cafbad7276e075e013Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9400000000-ebe96c13c62dda3cf07bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2590000000-e6787d5f1bcf7d88c4f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3920000000-53d460082506316314a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fe0-3900000000-9123d30223134c0cdf46Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017543
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound36690486
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.