Showing Compound Card for Pinocarveol (CDB000066)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (6) Show 12 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:23:31 UTC
Updated at2020-11-18 16:34:43 UTC
CannabisDB IDCDB000066
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePinocarveol
DescriptionPinocarveol, also known as 2(10)-pinen-3-ol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing 2 rings, fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. Thus, pinocarveol is an isoprenoid lipid molecule. Pinocarveol is very hydrophobic, practically insoluble in water and relatively neutral. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plant cell plastids (PMID: 23746261 ). 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. Pinocarveol is a clear viscous liquid with a balsam, camphor, and herbal taste. Pinocarveol is found, in highest concentrations in hyssops and rosemaries and has been detected in spearmints, sweet bay, wild celeries and cannabis (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC10H16O
Average Molecular Weight152.24
Monoisotopic Molecular Weight152.1201
IUPAC Name(1S,3S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol
Traditional Name(1S,3S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol
CAS Registry Number19889-99-7
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-/m0/s1
InChI KeyLCYXQUJDODZYIJ-YIZRAAEISA-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
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot 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-MSPinocarveol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1GABRA15q34-q35P14867 details
Gamma-aminobutyric acid receptor subunit alpha-2GABRA24p12P47869 details
Gamma-aminobutyric acid receptor subunit alpha-3GABRA3P34903 details
Gamma-aminobutyric acid receptor subunit alpha-4GABRA44p12P48169 details
Gamma-aminobutyric acid receptor subunit alpha-5GABRA515q11.2-q12P31644 details
Gamma-aminobutyric acid receptor subunit alpha-6GABRA65q34Q16445 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1GABRA15q34-q35P14867 details
Gamma-aminobutyric acid receptor subunit alpha-2GABRA24p12P47869 details
Gamma-aminobutyric acid receptor subunit alpha-3GABRA3P34903 details
Gamma-aminobutyric acid receptor subunit alpha-4GABRA44p12P48169 details
Gamma-aminobutyric acid receptor subunit alpha-5GABRA515q11.2-q12P31644 details
Gamma-aminobutyric acid receptor subunit alpha-6GABRA65q34Q16445 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound88297
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. Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. [PubMed:23746261 ]

Only showing the first 10 proteins. There are 12 proteins in total.

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Transporters

Enzyme Details
1. Gamma-aminobutyric acid receptor subunit alpha-1
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
Enzyme Details
2. Gamma-aminobutyric acid receptor subunit alpha-2
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA2
Uniprot ID:
P47869
Molecular weight:
51325.9
Enzyme Details
3. Gamma-aminobutyric acid receptor subunit alpha-3
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA3
Uniprot ID:
P34903
Molecular weight:
55164.1
Enzyme Details
4. Gamma-aminobutyric acid receptor subunit alpha-4
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA4
Uniprot ID:
P48169
Molecular weight:
61622.6
Enzyme Details
5. Gamma-aminobutyric acid receptor subunit alpha-5
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA5
Uniprot ID:
P31644
Molecular weight:
52145.6
Enzyme Details
6. Gamma-aminobutyric acid receptor subunit alpha-6
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA6
Uniprot ID:
Q16445
Molecular weight:
51023.7

Only showing the first 10 proteins. There are 12 proteins in total.

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