Showing Compound Card for ent-16-Kauren-19-ol (CDB005237)

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Record Information
Version1.0
Created at2020-04-17 19:23:04 UTC
Updated at2020-11-18 16:39:35 UTC
CannabisDB IDCDB005237
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nameent-16-Kauren-19-ol
Descriptionent-16-Kauren-19-ol, also known as ent-kaurenol or kaur-16-en-18-ol, belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. ent-16-Kauren-19-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). ent-16-Kauren-19-ol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Kaur-16-en-18-olHMDB
ent-Kaur-16-en-19-olHMDB
ent-KaurenolHMDB
Kaur-16-en-18-olHMDB
KaurenolHMDB
Kaur-16-en-15-olMeSH
ent-Kaur-16-en-15 beta-olMeSH
Chemical FormulaC20H32O
Average Molecular Weight288.47
Monoisotopic Molecular Weight288.2453
IUPAC Name{5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl}methanol
Traditional Name{5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-5-yl}methanol
CAS Registry Number2300-11-0
SMILES
CC1(CO)CCCC2(C)C3CCC4CC3(CC4=C)CCC12
InChI Identifier
InChI=1S/C20H32O/c1-14-11-20-10-7-16-18(2,13-21)8-4-9-19(16,3)17(20)6-5-15(14)12-20/h15-17,21H,1,4-13H2,2-3H3
InChI KeyTUJQVRFWMWRMIO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentKaurane diterpenoids
Alternative Parents
Substituents
  • Kaurane diterpenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.98ALOGPS
logP4.34ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.59ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity87.42 m³·mol⁻¹ChemAxon
Polarizability35.25 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSent-16-Kauren-19-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0c00-0290000000-be11e2be7f27ebf79b5eSpectrum
Predicted GC-MSent-16-Kauren-19-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007k-3339000000-46481719f37936ff8f00Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0090000000-ca1792c4b83ab336c4ed2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0390000000-8549754858080025627b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4950000000-d4a5ae3bc0b12906e4232016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-01f2dcb2014f7de995e12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0090000000-59d1cb39a5a19831fa882016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-0090000000-68fc9bf407c993e557f32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059i-0090000000-f27be353d28c12c48d7c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-1590000000-e5c351fefab461b8f00f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0609-4940000000-4f0c45f2b342dee368cb2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-81ee7157e3dd1ba9c37b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-81ee7157e3dd1ba9c37b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-5863dbdabfc047b6bff32021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0303568
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030849
KNApSAcK IDNot Available
Chemspider ID24784844
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound529650
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available