IMPPAT Phytochemical information: 
Cannabichromanone

Cannabichromanone
Summary

SMILES: CCCCCc1cc(O)c2c(c1)OC(C(C2=O)CCC(=O)C)(C)C
InChI: InChI=1S/C20H28O4/c1-5-6-7-8-14-11-16(22)18-17(12-14)24-20(3,4)15(19(18)23)10-9-13(2)21/h11-12,15,22H,5-10H2,1-4H3
InChIKey: NHZMSIOYBVIOAF-UHFFFAOYSA-N
DeepSMILES: CCCCCcccO)ccc6)OCCC6=O))CCC=O)C)))))C)C
Scaffold Graph/Node/Bond level: O=C1CCOc2ccccc21
Scaffold Graph/Node level: OC1CCOC2CCCCC12
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: cO; cOC; cC(=O)C; CC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Meroterpenoids
NP Classifier Class: Cannabinoids
Synonymous chemical names:
cannabichromanone
External chemical identifiers:
CID:CID_186690; SureChEMBL:SCHEMBL13214165
Chemical structure download


Cannabichromanone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 332.44
Log P RDKit 4.46
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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


Cannabichromanone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.748584


Cannabichromanone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.02
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No