Showing Compound Card for 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol (CDB000193)

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Record Information
Version1.0
Created at2020-03-18 23:28:14 UTC
Updated at2020-11-18 16:34:54 UTC
CannabisDB IDCDB000193
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol
DescriptionFenchol or 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Fenchol is a naturally occurring bicyclic monoterpenoid and an isomer of Borneol. 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 cyclation reactions to yield a diverse number of cyclic arrangements. Fenchol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a colorless or white solid with a characteristic scent found in basil and Aster and cannabis plants (PMID:6991645 ). Fenchol is used extensively in perfumery.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1S,2-endo)-1,3,3-Trimethylnorbornan-2-olChEBI
(1S,2S,4R)-endo-FencholChEBI
1,3,3-Trimethyl-2-norbornanolChEBI
2-FenchanolChEBI
alpha-FencholChEBI
alpha-Fenchyl alcoholChEBI
endo-alpha-FencholChEBI
endo-FencholChEBI
Fenchyl alcoholChEBI
(-)-alpha-Fenchyl alcoholKegg
a-FencholGenerator
Α-fencholGenerator
a-Fenchyl alcoholGenerator
Α-fenchyl alcoholGenerator
endo-a-FencholGenerator
endo-Α-fencholGenerator
(-)-a-Fenchyl alcoholGenerator
(-)-Α-fenchyl alcoholGenerator
Fenchol, ((endo)-(+-))-isomerMeSH
Fenchol, ((exo)-(+-))-isomerMeSH
Fenchol, (endo)-isomerMeSH
Fenchol, (1R-endo)-isomerMeSH
Fenchol, (1S-exo)-isomerMeSH
FencholMeSH
Fenchol, (1S-endo)-isomerMeSH
Fenchol, (exo)-isomerMeSH
a-Fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-olGenerator
Α-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-olGenerator
(1S,2S,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-olPhytoBank
(-)-endo-FencholPhytoBank
(-)-alpha-FencholPhytoBank
(-)-α-FencholPhytoBank
(1S-endo)-FencholPhytoBank
l-alpha-Fenchyl alcoholPhytoBank
l-α-Fenchyl alcoholPhytoBank
rel-(1R,2R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-olPhytoBank
(±)-alpha-FencholPhytoBank
(±)-α-FencholPhytoBank
dl-alpha-FencholPhytoBank
dl-α-FencholPhytoBank
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-olPhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
Traditional Name((endo)-(+-))-fenchol
CAS Registry Number2217-02-9
SMILES
CC1(C)[C@@H]2CC[C@@](C)(C2)[C@@H]1O
InChI Identifier
InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1
InChI KeyIAIHUHQCLTYTSF-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
  • Fenchane monoterpenoid
  • Bicyclic monoterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP2.3ALOGPS
logP2.15ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.16 m³·mol⁻¹ChemAxon
Polarizability18.52 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-MS1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-d82ad081287ed26399252019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-1900000000-94ea34fa991c83d8e3fa2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aca-9400000000-7d93799774481e0cda422019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-53ad86f1876aae2ee0672019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-747f855f1574c214338c2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fe0-0900000000-2389c65fe686d8639bb12019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-4094f7230adb483cf7e52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5c-6900000000-aabed757c552780da4722021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-9600000000-6fa6ff11a1ac49887bb32021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-459bafe52d5b103e88a62021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0303866
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029688
KNApSAcK IDC00052452
Chemspider ID388777
KEGG Compound IDC02344
BioCyc IDCPD-685
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15405
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 ]