Showing Compound Card for trans-Pinocarveol (CDB000714)

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Record Information
Version1.0
Created at2020-03-19 00:52:40 UTC
Updated at2020-12-07 19:07:42 UTC
CannabisDB IDCDB000714
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nametrans-Pinocarveol
DescriptionTrans-Pinocarveol or simply pinocarveol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Trans-Pinocarveol is the (1S,3R,5S)-stereoisomer of pinocarveol. It exists as a pale, clear, yellow oil that is weakly soluble in water (1 g/L). Trans-Pinocarveol is an extremely weak basic (essentially neutral) compound, based on its pKa. It has a herbal, pine, minty or balsamic odor and a comphoreous, pine or fir needle taste. Trans-Pincarveol is found in the essential oils of hop, myssop, grapefruit, rosemary, spearmint and wormwood. It has a role as a GABA(A) modulator (PMID: 24273211 ), a plant metabolite, a food additive, a cosmetic/fragrance agent and a volatile oil component. With regard to its positive GABA modulating effects, Pinocarveol (along with isopulegol, verbenol, and myrtenol) are particularly potent modifiers of GABA(A) receptor function and this interaction may lead to certain sedative effects found in plants or plant oils that contain this compound (PMID: 24273211 ). Trans-Pinocarveol is one of the compounds that have been identified in the essential oil of wild cannabis sativa plants (PMID: 6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-trans-2(10)-Pinen-3-olHMDB
(1S)-(-)-trans-PinocarveolHMDB
(1S,3R,5S)-(-)-2(10)-Pinen-3-olHMDB
L-PinocarveolHMDB
L-trans-PinocarveolHMDB
trans-(-)-PinocarveolHMDB
10-Pinen-3-olPhytoBank
2(10)-Pinen-3-olPhytoBank
6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3-olPhytoBank
PinocarveolePhytoBank
trans-2(10)-Pinen-3-olPhytoBank
(±)-trans-PinocarveolPhytoBank
Chemical FormulaC10H16O
Average Molecular Weight152.23
Monoisotopic Molecular Weight152.1201
IUPAC Name(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol
Traditional Name(1R,3S,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol
CAS Registry Number547-61-5
SMILES
CC1(C)[C@@H]2C[C@H]1C(=C)[C@@H](O)C2
InChI Identifier
InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9+/m1/s1
InChI KeyLCYXQUJDODZYIJ-VGMNWLOBSA-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
  • Pinane monoterpenoid
  • Bicyclic monoterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.24ALOGPS
logP1.63ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)17.94ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.17 m³·mol⁻¹ChemAxon
Polarizability17.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MStrans-Pinocarveol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0019-3900000000-6606ecc9cd06a6da5bd7Spectrum
Predicted GC-MStrans-Pinocarveol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i9-9220000000-95de3481bb916ce84e4fSpectrum
Predicted GC-MStrans-Pinocarveol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0900000000-6ff630040559510e3f1d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-b911719eff5a3760007f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-0900000000-7dde3d5da047714de1932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-1384a080edbf08e603852016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-cce040d437e6c1eee01a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0900000000-52674d0954f32b6b30042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-5f1fa6e5001f7cc956712021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-88a021c06131e7896a302021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-b40ea28a1af5b2c22f292021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-0900000000-50f9a6a23df6edc6a85c2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0036128
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014367
KNApSAcK IDC00011040
Chemspider ID79661
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1201530
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  3. Kessler A, Sahin-Nadeem H, Lummis SC, Weigel I, Pischetsrieder M, Buettner A, Villmann C: GABA(A) receptor modulation by terpenoids from Sideritis extracts. Mol Nutr Food Res. 2014 Apr;58(4):851-62. doi: 10.1002/mnfr.201300420. Epub 2013 Nov 24. [PubMed:24273211 ]