Showing Compound Card for Friedelanol (CDB000221)

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Record Information
Version1.0
Created at2020-03-19 00:25:17 UTC
Updated at2020-11-18 16:34:56 UTC
CannabisDB IDCDB000221
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFriedelanol
DescriptionFriedelanol belongs to the class of organic compounds known as triterpenoids. Friedelanol is biochemically a triterpenoid and it is one of two triterpenes found in cannabis plants (PMID:6991645 ). Triterpenoids are molecules that contain 30 carbon atoms and are comprised of six isoprene units. Triterpenes are the most diverse class of secondary metabolites and can be found in all living organisms. The biosynthesis of triterpenes occurs through the mevalonic acid pathway (MVA), mainly in the cytosol. A key intermediate in the biosynthesis of triterpenoids is 2,3-oxidosqualene, which undergoes several cyclization reactions to yield a diverse number of cyclic arrangements.
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC30H52O
Average Molecular Weight428.75
Monoisotopic Molecular Weight428.4018
IUPAC Name(3R,4R,4aS,6aR,6bS,8aS,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-ol
Traditional Name(3R,4R,4aS,6aR,6bS,8aS,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-hexadecahydropicen-3-ol
CAS Registry Number5085-72-3
SMILES
C[C@H]1[C@H](O)CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3CC(C)(C)CC[C@@]3(C)CC[C@@]12C
InChI Identifier
InChI=1S/C30H52O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20-24,31H,9-19H2,1-8H3/t20-,21+,22+,23+,24+,26-,27+,28-,29-,30-/m0/s1
InChI KeyXCDQFROEGGNAER-OUJFBGHFSA-N
Chemical Taxonomy
ClassificationNot classified
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
logP6.38ALOGPS
logP7.73ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)19.22ChemAxon
pKa (Strongest Basic)-0.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity131.13 m³·mol⁻¹ChemAxon
Polarizability54.03 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFriedelanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
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
ReceptorsNot Available
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 CompoundNot Available
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 ]