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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 21:15:59 UTC
Update Date2020-02-26 21:24:37 UTC
HMDB IDHMDB0003450
Secondary Accession Numbers
  • HMDB0006410
  • HMDB03450
  • HMDB06410
Metabolite Identification
Common Name(-)-trans-Carveol
Description(-)-trans-Carveol, also known as (1S,5R)-carveol, 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. Thus, (-)-trans-carveol is considered to be an isoprenoid lipid molecule (-)-trans-Carveol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752277
Synonyms
ValueSource
(-)-(4R,6S)-trans-CarveolChEBI
(1S,5R)-CarveolChEBI
CarveolHMDB
(-)-(4R,6S)-CarveolHMDB
(-)-trans-CarveolHMDB
(1S,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-olHMDB
(E)-CarveolHMDB
(±)-trans-CarveolHMDB
trans-(-)-CarveolHMDB
trans-5-(1-Methylethenyl)-2-methyl-2-cyclohexenolHMDB
trans-CarveolHMDB
trans-Mentha-1,8-dien-6-olHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name(1S,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Traditional Name(-)-trans-carveol
CAS Registry Number2102-58-1
SMILES
CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1
InChI Identifier
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3/t9-,10+/m1/s1
InChI KeyBAVONGHXFVOKBV-ZJUUUORDSA-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
  • 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

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.12GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
Water Solubility2.82 g/LALOGPS
logP2.41ALOGPS
logP1.99ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)18.21ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48 m³·mol⁻¹ChemAxon
Polarizability18 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)splash10-05nf-9700000000-a75055e28480ba00b820Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9300000000-0497c064b7fcb0223af5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05nf-9700000000-a75055e28480ba00b820Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9300000000-0497c064b7fcb0223af5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05nf-9700000000-a75055e28480ba00b820Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9300000000-0497c064b7fcb0223af5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05nf-9700000000-a75055e28480ba00b820Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a5c-9300000000-0497c064b7fcb0223af5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0040-9300000000-900d20824e13ff7b371aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-059l-9420000000-c8fe9a59dae7a88e5d86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-1900000000-6cbdaa00e43b6a5f1466Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-7900000000-b55dc6268bf1d9facfabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9200000000-82efaa1d3034c0a127adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-63662b96265d54ab95acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-fb53bb25a46fab88d48aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frl-6900000000-b30096dc2484f9341f67Spectrum
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 IDFDB013717
KNApSAcK IDC00000814
Chemspider ID85031
KEGG Compound IDC00964
BioCyc IDNot Available
BiGG ID36494
Wikipedia LinkCarveol
METLIN ID6934
PubChem Compound94221
PDB IDNot Available
ChEBI ID15389
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceWouter, Adrian Duetz; Witholt, Bernard; Jourdat, Catherine. Process for the preparation of trans-carveol. Eur. Pat. Appl. (2002), 12 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
Reactions
d-Limonene + NADPH + Oxygen → (-)-trans-Carveol + NADP + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
Reactions
d-Limonene + NADPH + Oxygen → (-)-trans-Carveol + NADP + Waterdetails