Showing Compound Card for (-)-Isoborneol (CDB000184)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-18 23:27:54 UTC
Updated at2020-12-07 19:07:14 UTC
CannabisDB IDCDB000184
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(-)-Isoborneol
Description(-)-Isoborneol, also known as borneol, 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 (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. Borneol can be synthesized by reducing camphor by the Meerwein–Ponndorf–Verley reaction, a reversible, inexpensive process. The isomer isoborneol can be produced in the kinetically controlled reduction of camphor with sodium borohydride, which is fast and irreversible. (-)-Isoborneol is neutral compound, a white crystalline solid with a balsamic camphoreous herbal woody odor and camphoreous minty herbal earthy woody flavor ( Ref:DOI ). Borneol or isoborneol is a naturally occurring organic compound found in the essential oil of many plants such as camphorweed, mugwort, beautyberry, Ngai camphor, aromatic ginger and in cannabis plants (PMID:6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
FEMA 2158HMDB
BorneolMeSH, HMDB
Isoborneol, (exo)-isomerMeSH, HMDB
Isoborneol, (1R-exo)-isomerMeSH, HMDB
Isoborneol, (endo)-isomerMeSH, HMDB
Isoborneol, (endo-(+-))-isomerMeSH, HMDB
Isoborneol, (1R-endo)-isomerMeSH, HMDB
IsoborneolMeSH, HMDB
(-)-(2R)-IsoborneolHMDB
(-)-Bornan-2-exo-olHMDB
(-)-IsoborneolHMDB
(1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-olHMDB
(R,R,R)-(-)-IsoborneolHMDB
2-exo-Bornyl alcoholHMDB
Isobornyl alcoholHMDB
exo-2-Hydroxy-1,7,7-trimethylnorbornaneHMDB
l-IsoborneolPhytoBank
(±)-IsoborneolPhytoBank
dl-IsoborneolPhytoBank
NSC 26350PhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
Traditional Name(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
CAS Registry Number10334-13-1
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-MRTMQBJTSA-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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point212 °CNot Available
Boiling PointNot AvailableNot Available
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
Polarizability18.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(-)-Isoborneol, non-derivatized, GC-MS Spectrumsplash10-0005-9200000000-66a44698625f85db99daSpectrum
Predicted GC-MS(-)-Isoborneol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0bt9-1900000000-561b837a8b44dbfaea56Spectrum
Predicted GC-MS(-)-Isoborneol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03k9-6930000000-42c843fe7b6dc6e988d9Spectrum
Predicted GC-MS(-)-Isoborneol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-1900000000-5ca1187f552ff564ef4c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-000i-3900000000-4d9d1609f8db2aa452262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-5900000000-96b6c2a93a81f990e5cd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000j-9800000000-e59940adf942eacbdd0e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-001a-9500000000-c53784fc1bb63df575f02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0012-9300000000-7bb32334950aa43e174d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9200000000-b624a408fde0b0b95fc32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000t-9000000000-dd98da52ad93c01d83a22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-000t-9000000000-cfdbe937662b3a812a632020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00l2-9000000000-367cf23b451dbe8547462020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-017i-9000000000-fe79ebe8bd77394af3a02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0693-9000000000-b08ed9d6f97e835191b92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-05r3-9000000000-d0231d31055bf6da8fc42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000t-9000000000-12d91b5ab3379725f8a32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-fb41d95361a6747c13942020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-59ba5428676cdc8984e32020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-7eaa92cdc2cb1dd17c332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-fb1222abb6cef74eb0832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-2900000000-622438b8bd224a755c472016-08-03View 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
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-4900000000-c5fb0f5b567a4f9fada92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-090r-9400000000-3329d0b3e6f71527a4bc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1ab95ec8cd37ae806b102021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035819
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014581
KNApSAcK IDC00011022
Chemspider ID4882019
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6321405
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 ]