IMPPAT Phytochemical information: 
Canniprene

Canniprene
Summary

SMILES: COc1cc(CCc2ccc(c(c2CC=C(C)C)O)OC)cc(c1)O
InChI: InChI=1S/C21H26O4/c1-14(2)5-9-19-16(8-10-20(25-4)21(19)23)7-6-15-11-17(22)13-18(12-15)24-3/h5,8,10-13,22-23H,6-7,9H2,1-4H3
InChIKey: NGQFSSVGVDXEOE-UHFFFAOYSA-N
DeepSMILES: COcccCCcccccc6CC=CC)C)))))O))OC))))))))ccc6)O
Scaffold Graph/Node/Bond level: c1ccc(CCc2ccccc2)cc1
Scaffold Graph/Node level: C1CCC(CCC2CCCCC2)CC1
Scaffold Graph level: C1CCC(CCC2CCCCC2)CC1
Functional groups: cOC; CC=C(C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Stilbenes
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Stilbenoids
NP Classifier Class: Monomeric stilbenes
Synonymous chemical names:
canniprene
External chemical identifiers:
CID:CID_53439651; ChEMBL:CHEMBL4082457; ZINC:ZINC000013383072; SureChEMBL:SCHEMBL12954547; MolPort-035-706-528
Chemical structure download


Canniprene
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 342.44
Log P RDKit 4.41
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 4
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 14
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


Canniprene
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.73


Canniprene
ADME 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 -4.63
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No