Showing Compound Card for Obtusifoliol (CDB005333)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:32:41 UTC
Updated at2020-12-07 19:11:58 UTC
CannabisDB IDCDB005333
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameObtusifoliol
DescriptionObtusifoliol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Obtusifoliol is an extremely weak basic (essentially neutral) compound (based on its pKa). Obtusifoliol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4,4-Dimethyl-14a-hydroxymethyl-5a-cholesta-8,24-dien-3b-olHMDB
4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-olHMDB
Chemical FormulaC30H50O2
Average Molecular Weight442.72
Monoisotopic Molecular Weight442.3811
IUPAC Name11-(hydroxymethyl)-2,6,6,15-tetramethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name11-(hydroxymethyl)-2,6,6,15-tetramethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry NumberNot Available
SMILES
CC(CCC=C(C)C)C1CCC2(CO)C3=C(CCC12C)C1(C)CCC(O)C(C)(C)C1CC3
InChI Identifier
InChI=1S/C30H50O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h9,21-22,25-26,31-32H,8,10-19H2,1-7H3
InChI KeyDWVYYKFZEDMMPU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.54ALOGPS
logP6.43ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)19.43ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity136.32 m³·mol⁻¹ChemAxon
Polarizability55.97 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSObtusifoliol, 1 TMS, GC-MS Spectrumsplash10-0a5c-4910000000-dad41d67ee45a726de74Spectrum
Predicted GC-MSObtusifoliol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03fr-1014900000-f3613a2ad5ce1cdd7e77Spectrum
Predicted GC-MSObtusifoliol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3100290000-b6ca81fc81d7dac714fcSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0001900000-6d455ee2fdccf0efa59a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r0-2218900000-f05f2da084e7f29ea2fa2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-5429100000-24c787ad15da694c02882016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-30446d4866c57f241cbe2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0001900000-da89b55f5042a729bc342016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-1009500000-ef0a5cf54c21d47627522016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-4006900000-b8ad319d77e983afb8402021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cdl-9006100000-4eb00b98ff285c5f2de92021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9227000000-2b2264d23b7fc86de5f32021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-849799f7ece1fdb1b84b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000900000-75b268393786aaa369062021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dv-0002900000-71f0730c90ea11015a972021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Lanosterol 14-alpha demethylaseCYP51A17q21.2Q16850 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Lanosterol 14-alpha demethylaseCYP51A17q21.2Q16850 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0304022
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030262
KNApSAcK IDC00007317
Chemspider ID570838
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound656449
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lanosterol 14-alpha demethylase
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular weight:
57277.81