Showing Compound Card for ent-16-Kauren-19-al (CDB005238)

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Record Information
Version1.0
Created at2020-04-17 19:23:10 UTC
Updated at2020-12-07 19:11:49 UTC
CannabisDB IDCDB005238
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nameent-16-Kauren-19-al
Descriptionent-16-Kauren-19-al, also known as ent-kaurenal or kaur-16-en-18-al, 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-al is an extremely weak basic (essentially neutral) compound (based on its pKa). ent-16-Kauren-19-al 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-alHMDB
4alpha-Kaur-16-en-18-alHMDB
ent-Kaur-16-en-19-alHMDB
ent-KaurenalHMDB
Kaur-16-en-18-alHMDB
KaurenalHMDB
Chemical FormulaC20H30O
Average Molecular Weight286.45
Monoisotopic Molecular Weight286.2297
IUPAC Name5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde
Traditional Name5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carbaldehyde
CAS Registry Number14046-84-5
SMILES
CC1(CCCC2(C)C3CCC4CC3(CC4=C)CCC12)C=O
InChI Identifier
InChI=1S/C20H30O/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/h13,15-17H,1,4-12H2,2-3H3
InChI KeyJCAVDWHQNFTFBW-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
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point113 - 116 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.06ALOGPS
logP4.65ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.44 m³·mol⁻¹ChemAxon
Polarizability34.5 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-al, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-0390000000-5066c6ff5ac3394b7e24Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-298817bc1c5a8425f8b42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1490000000-d2cb4b386da1518703662015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dl-5950000000-d682f0be28bb863981cb2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-e3e638dc721ce6e6034d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-55c91b00a1b1de9aa5632015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-3090000000-718bcad02030bf8912682015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0090000000-8c2269ce2b70ba8b35f92021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0590000000-eb372332cd1afe9e79ec2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gv-1920000000-c038e251d6e87ccc46f12021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-9414264daccf69560d4d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-9414264daccf69560d4d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-dbb2840a01d310ec2f402021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0304347
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030847
KNApSAcK IDNot Available
Chemspider ID21121170
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound529648
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available