Showing Compound Card for Borneol (CDB000462)

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Record Information
Version1.0
Created at2020-03-19 00:38:11 UTC
Updated at2020-12-07 19:07:26 UTC
CannabisDB IDCDB000462
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBorneol
DescriptionBorneol, 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 the plastids. 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. Borneol is a secondary alcohol and there are two enantiomers of borneol, d-(+)-borneol and l-(–)-borneol, which can be found in nature. Borneol is a component of many essential oils and it is a natural insect repellent. Additionally, borneol is one of many terpenoids that are known to occur in cannabis plants (PMID: 6991645 ). Borneol can be found in several species of Heterotheca, Artemisia, Callicarpa, Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1R,2S,4R)-(+)-BorneolChEBI
(1R,2S,4R)-BorneolChEBI
(1R-endo)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-olChEBI
BorneocamphorChEBI
D-BorneolChEBI
endo-2-BornanolChEBI
Sumatra camphorChEBI
BorneolMeSH
IsoborneolMeSH
Isoborneol, (1R-endo)-isomerMeSH
Isoborneol, (1R-exo)-isomerMeSH
Isoborneol, (1S-endo)-isomerMeSH
Isoborneol, (1S-exo)-isomerMeSH
Isoborneol, (endo)-isomerMeSH
Isoborneol, (endo-(+-))-isomerMeSH
Isoborneol, (exo)-isomerMeSH
(+)-(2S)-BorneolPhytoBank
(+)-2-BorneolPhytoBank
(+)-BorneolPhytoBank
(+)-endo-BorneolPhytoBank
(1R)-(+)-BorneolPhytoBank
(1R)-endo-BorneolPhytoBank
(1R,2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-olPhytoBank
d-(+)-BorneolPhytoBank
(±)-BorneolPhytoBank
2-BorneolPhytoBank
2-endo-Bornyl alcoholPhytoBank
dl-BorneolPhytoBank
endo-(±)-Bornan-2-olPhytoBank
endo-2-Hydroxy-1,7,7-trimethylnorbornanePhytoBank
endo-BorneolPhytoBank
CampholPhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
Traditional Name(+)-borneol
CAS Registry Number464-43-7
SMILES
CC1(C)[C@@H]2CC[C@@]1(C)[C@@H](O)C2
InChI Identifier
InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m1/s1
InChI KeyDTGKSKDOIYIVQL-WEDXCCLWSA-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
  • Bicyclic monoterpenoid
  • Bornane monoterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point208 °CWikipedia
Boiling Point213 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.83ALOGPS
logP1.99ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.31 m³·mol⁻¹ChemAxon
Polarizability18.47 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSBorneol, non-derivatized, GC-MS Spectrumsplash10-0002-9100000000-9d4f533b5d9cf6146f3eSpectrum
Predicted GC-MSBorneol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-7eaa92cdc2cb1dd17c332016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-fb1222abb6cef74eb0832016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-2900000000-622438b8bd224a755c472016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-b64fc5b28acf2b8ce6ee2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-404830ee9ef93bfec2b82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fki-2900000000-5d8542e9c4643c74fa542016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.09 mg/g dry wt
    • David S. Wishart,...
 details
Alien Dawg (Indica dominant)Detected and Quantified0.12 +/- 0.02 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.13 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.07 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.27 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.08 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.08 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.07 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine Dream (Sativa dominant)Detected and Quantified0.06 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00011023
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6552009
PDB IDNot Available
ChEBI ID15393
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 ]