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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:08:52 UTC
Update Date2019-07-23 06:20:18 UTC
HMDB IDHMDB0036078
Secondary Accession Numbers
  • HMDB36078
Metabolite Identification
Common Name(-)-Isopulegol
Description(-)-Isopulegol belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (-)-Isopulegol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862818
Synonyms
ValueSource
(-)-L-IsopulegolHMDB
(1R,3R,4S)-(-)-p-Menth-8-en-3-olHMDB
5-Methyl-2-(1-methylethenyl)-(1R,2S,5R)-cyclohexanolHMDB
L-IsopulegolHMDB
IsopulegolMeSH
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol
Traditional Name(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol
CAS Registry Number89-79-2
SMILES
C[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C
InChI Identifier
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
InChI KeyZYTMANIQRDEHIO-KXUCPTDWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point78 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.28 g/LALOGPS
logP2.69ALOGPS
logP2.32ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)19.47ChemAxon
pKa (Strongest Basic)-0.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.22 m³·mol⁻¹ChemAxon
Polarizability18.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066u-9100000000-b05fac870c7dbc59229bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-015c-9100000000-48d93dc21b89adaab452Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06di-9200000000-2ce50fb75d3deb9eb8e7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066u-9100000000-b05fac870c7dbc59229bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-015c-9100000000-48d93dc21b89adaab452Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06di-9200000000-2ce50fb75d3deb9eb8e7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9400000000-488f8682a6cd647ab006Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-08mu-9620000000-8ac174806e5dc19696e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-b784ae5f8c92cdff077aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n1-8900000000-4ca9df3290f613ad8158Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9000000000-f9df6d8c024d2913e865Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-13767d8f01d3cbb7cc97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-b47c5c16777566ad4c5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fs-6900000000-1d5990268c4a20c74c15Spectrum
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 IDFDB014912
KNApSAcK IDC00010938
Chemspider ID149356
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound170833
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.