IMPPAT Phytochemical information: 
Cannabinol

Cannabinol
Summary

SMILES: CCCCCc1cc(O)c2-c3cc(C)ccc3C(Oc2c1)(C)C
InChI: InChI=1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3
InChIKey: VBGLYOIFKLUMQG-UHFFFAOYSA-N
DeepSMILES: CCCCCcccO)c-cccC)ccc6COc%10c%14)))C)C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)COc1ccccc1-2
Scaffold Graph/Node level: C1CCC2C(C1)COC1CCCCC12
Scaffold Graph level: C1CCC2C(C1)CCC1CCCCC12
Functional groups: cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Polyketides|Terpenoids
NP Classifier Superclass: Meroterpenoids
NP Classifier Class: Cannabinoids
Synonymous chemical names:
cannabinol
External chemical identifiers:
CID:2543; ChEMBL:CHEMBL74415; ChEBI:3360; ZINC:ZINC000001530833; FDASRS:7UYP6MC9GH; SureChEMBL:SCHEMBL121085
Chemical structure download


Cannabinol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 310.44
Log P RDKit 5.73
Topological polar surface area (Å2) RDKit 29.46
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Cannabinol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7309


Cannabinol
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -3.86
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes


Cannabinol
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000358511CNR1904
ENSP00000363596CNR2855
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.