Record Information
Version1.0
Created at2020-03-19 00:32:19 UTC
Updated at2020-12-07 19:07:22 UTC
CannabisDB IDCDB000349
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameViridiflorene
DescriptionViridiflorene also known as leden, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol (PMID: 7640522 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Viridiflorene is a hydrophobic, neutral molecule that is insoluble in water. It exists as a clear, colorless oil. Viridiflorene can be found in a number of plant foods and spices such as allspice, sweet basil, sweet marjoram, eucalyptus, common oregano, sage, thyme and rosemary, which makes viridiflorene a potential biomarker for the consumption of these food products. Viridiflorene is one of more than 140 terpenoids found in cannabis plants (PMID: 6991645 ).
Structure
Thumb
Synonyms
ValueSource
LedenChEBI
LedeneChEBI
(+)-LedenePhytoBank
(+)-ViridiflorenePhytoBank
Chemical FormulaC15H24
Average Molecular Weight204.35
Monoisotopic Molecular Weight204.1878
IUPAC Name(1aR,7R,7aS,7bR)-1,1,4,7-tetramethyl-1H,1aH,2H,3H,5H,6H,7H,7aH,7bH-cyclopropa[e]azulene
Traditional Nameleden
CAS Registry Number21747-46-6
SMILES
C[C@@H]1CCC2=C(C)CC[C@@H]3[C@H]([C@H]12)C3(C)C
InChI Identifier
InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10,12-14H,5-8H2,1-4H3/t10-,12-,13-,14-/m1/s1
InChI KeyWGTRJVCFDUCKCM-FMKGYKFTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct Parent5,10-cycloaromadendrane sesquiterpenoids
Alternative Parents
Substituents
  • 5,10-cycloaromadendrane sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.39ALOGPS
logP4.04ChemAxon
logS-4.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.5 m³·mol⁻¹ChemAxon
Polarizability26.12 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSViridiflorene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03g0-2900000000-63472047d599d586b269Spectrum
Predicted GC-MSViridiflorene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSViridiflorene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-e64f631cf60f6a1f7a052017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0590000000-9f28e598a4bda54104422017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j70-4900000000-466b15f55197d449e74e2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6589dee75f8602eecab52017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-4952e3011b37d390d5012017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-009i-1910000000-dc6219dfb1223f764f772017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0290000000-aa81f6087aa508ac1dbd2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-4a9d324bd2752a856f352021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9710000000-791d4a4cf8c97d62cd5a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009y-9400000000-8af31644afd13bb682f02021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0061849
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00021220
Chemspider IDNot Available
KEGG Compound IDC20162
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10910653
PDB IDNot Available
ChEBI ID63444
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 ]