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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:08:52 UTC
Update Date2021-10-13 06:53:37 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. Based on a literature review a small amount of articles have been published on (-)-Isopulegol.
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point78 °CNot Available
Boiling Point216.00 to 218.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility308.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.724 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.28 g/LALOGPS
logP10(2.69) g/LALOGPS
logP10(2.32) g/LChemAxon
logS10(-2.1) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.21931661259
DarkChem[M-H]-134.44431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-IsopulegolC[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C1593.0Standard polar33892256
(-)-IsopulegolC[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C1166.7Standard non polar33892256
(-)-IsopulegolC[C@@H]1CC[C@H]([C@H](O)C1)C(C)=C1181.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-Isopulegol,1TMS,isomer #1C=C(C)[C@@H]1CC[C@@H](C)C[C@H]1O[Si](C)(C)C1256.2Semi standard non polar33892256
(-)-Isopulegol,1TBDMS,isomer #1C=C(C)[C@@H]1CC[C@@H](C)C[C@H]1O[Si](C)(C)C(C)(C)C1487.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (-)-Isopulegol EI-B (Non-derivatized)splash10-066u-9100000000-b05fac870c7dbc59229b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Isopulegol EI-B (Non-derivatized)splash10-015c-9100000000-48d93dc21b89adaab4522017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Isopulegol EI-B (Non-derivatized)splash10-06di-9200000000-2ce50fb75d3deb9eb8e72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Isopulegol EI-B (Non-derivatized)splash10-066u-9100000000-b05fac870c7dbc59229b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Isopulegol EI-B (Non-derivatized)splash10-015c-9100000000-48d93dc21b89adaab4522018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Isopulegol EI-B (Non-derivatized)splash10-06di-9200000000-2ce50fb75d3deb9eb8e72018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (-)-Isopulegol GC-EI-Q (Non-derivatized)splash10-01bc-9200000000-ad4eceffb3f590ef24262020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Isopulegol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9400000000-488f8682a6cd647ab0062017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Isopulegol GC-MS (1 TMS) - 70eV, Positivesplash10-08mu-9620000000-8ac174806e5dc19696e42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Isopulegol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 10V, Positive-QTOFsplash10-052r-0900000000-b784ae5f8c92cdff077a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 20V, Positive-QTOFsplash10-05n1-8900000000-4ca9df3290f613ad81582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 40V, Positive-QTOFsplash10-0aor-9000000000-f9df6d8c024d2913e8652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 10V, Negative-QTOFsplash10-0udi-0900000000-13767d8f01d3cbb7cc972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 20V, Negative-QTOFsplash10-0udi-0900000000-b47c5c16777566ad4c5a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 40V, Negative-QTOFsplash10-08fs-6900000000-1d5990268c4a20c74c152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 10V, Negative-QTOFsplash10-0udi-0900000000-e9de8c42355b9a8b0cd02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 20V, Negative-QTOFsplash10-0udi-0900000000-e9f66794fa59715924fe2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 40V, Negative-QTOFsplash10-0159-2900000000-2710d4b6c4ccaf8079dc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 10V, Positive-QTOFsplash10-01ot-9500000000-064bca782f04398c7d602021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 20V, Positive-QTOFsplash10-00lv-9200000000-7f08745e9bf166d9ce232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isopulegol 40V, Positive-QTOFsplash10-05mo-9000000000-700d21150758cfc08b712021-09-25Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1014351
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.