Record Information
Version1.0
Created at2020-03-18 23:23:40 UTC
Updated at2020-12-07 19:07:02 UTC
CannabisDB IDCDB000070
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFenchone
DescriptionFenchone belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, fenchone is an isoprenoid lipid molecule. Fenchone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Fenchone is a colorless oily liquid with a bitter, camphor, and cedar leaf taste. Fenchone occurs in fennels (https://doi.org/10.1111/j.2042-7158.1968.tb09783.x), rosemaries, and star anises making fenchone a potential biomarker for the consumption of these foods. Fenchone was detected in the fresh bud of the cannabis plant (PMID: 8984153 ). Fenchone is used as a flavor in foods such as candy and baked goods and to add scents to soaps, detergents, perfumes and lotions. It also an insect repellent.
Structure
Thumb
Synonyms
ValueSource
(-)-FenchoneChEBI
(1R)-(-)-FenchoneChEBI
(1R)-FenchoneChEBI
(1R,4S)-(-)-FenchoneChEBI
(1R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-oneChEBI
(R)-(-)-FenchonePhytoBank
(R)-FenchonePhytoBank
L-(-)-FenchonePhytoBank
l-FenchonePhytoBank
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-onePhytoBank
(±)-FenchonePhytoBank
1,3,3-Trimethyl-2-norbornanonePhytoBank
1,3,3-TrimethylnorcamphorPhytoBank
dl-FenchonePhytoBank
Chemical FormulaC10H16O
Average Molecular Weight152.24
Monoisotopic Molecular Weight152.1201
IUPAC Name(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
Traditional Namefenchone, (+-)-
CAS Registry Number7787-20-4
SMILES
CC1(C)[C@H]2CC[C@](C)(C2)C1=O
InChI Identifier
InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1
InChI KeyLHXDLQBQYFFVNW-OIBJUYFYSA-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
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point6.1 °CWikipedia
Boiling Point193.5 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.54ALOGPS
logP3.06ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.54 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
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
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 2 member 10TAS2R1012p13Q9NYW0 details
Taste receptor type 2 member 16TAS2R167q31.1-q31.3|7q31Q9NYV7 details
Taste receptor type 2 member 40TAS2R407q34P59535 details
Taste receptor type 2 member 3TAS2R37q31.3-q32Q9NYW6 details
Taste receptor type 2 member 4TAS2R47q31.3-q32Q9NYW5 details
Taste receptor type 2 member 7TAS2R712p13Q9NYW3 details
Taste receptor type 2 member 9TAS2R912p13Q9NYW1 details
Taste receptor type 2 member 50TAS2R5012p13.2P59544 details
Taste receptor type 2 member 38TAS2R387q34P59533 details
Taste receptor type 2 member 31TAS2R3112p13.2P59538 details
Taste receptor type 2 member 1TAS2R15p15.31Q9NYW7 details
Taste receptor type 2 member 20TAS2R2012p13.2P59543 details
Taste receptor type 2 member 39TAS2R397q34P59534 details
Taste receptor type 2 member 19TAS2R1912p13.2P59542 details
Taste receptor type 2 member 45TAS2R45P59539 details
Taste receptor type 2 member 30TAS2R3012p13.2P59541 details
Taste receptor type 2 member 42TAS2R42Q7RTR8 details
Taste receptor type 2 member 41TAS2R417q35P59536 details
Taste receptor type 2 member 43TAS2R4312p13.2P59537 details
Taste receptor type 2 member 5TAS2R57q34Q9NYW4 details
Taste receptor type 2 member 46TAS2R4612p13.2P59540 details
Taste receptor type 2 member 13TAS2R1312p13.2Q9NYV9 details
Taste receptor type 2 member 60TAS2R607q35P59551 details
Taste receptor type 2 member 8TAS2R812p13.2Q9NYW2 details
Taste receptor type 2 member 14TAS2R1412p13.2Q9NYV8 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 Compound82229
PDB IDNot Available
ChEBI ID36612
References
General References
  1. Ross SA, ElSohly MA: The volatile oil composition of fresh and air-dried buds of Cannabis sativa. J Nat Prod. 1996 Jan;59(1):49-51. doi: 10.1021/np960004a. [PubMed:8984153 ]

Only showing the first 10 proteins. There are 25 proteins in total.

Only showing the first 10 proteins. There are 25 proteins in total.