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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:09:05 UTC
Update Date2022-03-07 02:54:46 UTC
HMDB IDHMDB0036082
Secondary Accession Numbers
  • HMDB36082
Metabolite Identification
Common Name(-)-cis-Carveol
Description(-)-cis-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, (-)-cis-carveol is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (-)-cis-Carveol.
Structure
Data?1563862818
Synonyms
ValueSource
(-)-(4R,6R)-cis-CarveolChEBI
(-)-cis-P-Mentha-1,8-dien-6-olHMDB
(1R)-cis-CarveolHMDB
(1R,5R)-(-)-cis-CarveolHMDB
(1R-cis)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-olHMDB
(1R-cis)-2-Methyl-5-isopropenyl-2-cyclohexen-1-olHMDB
(4R,6R)-P-Mentha-1,8-dien-6-olHMDB
2-Methyl-5-(1-methylethenyl)-(1R,5R)-2-cyclohexen-1-olHMDB
2-Methyl-5-(1-methylethenyl)-(1R-cis)-2-cyclohexen-1-olHMDB
cis-(-)-CarveolHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name(1R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Traditional Name(-)-cis-carveol
CAS Registry Number2102-59-2
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-NXEZZACHSA-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

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point24 - 25 °CNot Available
Boiling Point101.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility519.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.819 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability18.39 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]+137.50731661259
DarkChem[M-H]-134.36731661259
DeepCCS[M+H]+141.74530932474
DeepCCS[M-H]-139.34930932474
DeepCCS[M-2H]-173.3930932474
DeepCCS[M+Na]+147.85930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-cis-CarveolCC(=C)[C@@H]1CC=C(C)[C@H](O)C11803.9Standard polar33892256
(-)-cis-CarveolCC(=C)[C@@H]1CC=C(C)[C@H](O)C11198.7Standard non polar33892256
(-)-cis-CarveolCC(=C)[C@@H]1CC=C(C)[C@H](O)C11214.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-cis-Carveol,1TMS,isomer #1C=C(C)[C@@H]1CC=C(C)[C@H](O[Si](C)(C)C)C11295.1Semi standard non polar33892256
(-)-cis-Carveol,1TBDMS,isomer #1C=C(C)[C@@H]1CC=C(C)[C@H](O[Si](C)(C)C(C)(C)C)C11538.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-cis-Carveol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0040-9300000000-900d20824e13ff7b371a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-cis-Carveol GC-MS (1 TMS) - 70eV, Positivesplash10-059l-9420000000-c8fe9a59dae7a88e5d862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-cis-Carveol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9300000000-ae7d8ba5fb08ce6f40172015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 10V, Positive-QTOFsplash10-0f79-1900000000-6cbdaa00e43b6a5f14662016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 20V, Positive-QTOFsplash10-0f79-7900000000-f5a0579ac8857d525d072016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 40V, Positive-QTOFsplash10-1000-9200000000-7631d4c31e9b10b2e57b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 10V, Negative-QTOFsplash10-0udi-0900000000-6165a03d2d9c9e84c43f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 20V, Negative-QTOFsplash10-0udi-0900000000-fb53bb25a46fab88d48a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 40V, Negative-QTOFsplash10-0f79-6900000000-985654b955f212c9dee92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 10V, Negative-QTOFsplash10-0udi-0900000000-c751b1e6b18ebbd8226b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 20V, Negative-QTOFsplash10-0ue9-0900000000-ff7b348d24f4a9fae7682021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 40V, Negative-QTOFsplash10-0159-5900000000-32379e3babd1cfac9d582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 10V, Positive-QTOFsplash10-000l-7900000000-14152f364bee2002ab862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 20V, Positive-QTOFsplash10-002f-9100000000-c417dcb5d6ff023a5c442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-cis-Carveol 40V, Positive-QTOFsplash10-0006-9000000000-33b66b0d611b3c8dca5f2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB014918
KNApSAcK IDC00029971
Chemspider ID292842
KEGG Compound IDC11395
BioCyc IDCPD-10050
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound330573
PDB IDNot Available
ChEBI ID227
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1053801
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.