IMPPAT Phytochemical information: 
Cubebin
Cubebin
Summary

SMILES: O[C@H]1OC[C@@H]([C@H]1Cc1ccc2c(c1)OCO2)Cc1ccc2c(c1)OCO2
InChI: InChI=1S/C20H20O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15,20-21H,5-6,9-11H2/t14-,15+,20-/m0/s1
InChIKey: DIYWRNLYKJKHAM-MDOVXXIYSA-N
DeepSMILES: O[C@H]OC[C@@H][C@H]5Ccccccc6)OCO5))))))))))Ccccccc6)OCO5
Scaffold Graph/Node/Bond level: c1cc2c(cc1CC1COCC1Cc1ccc3c(c1)OCO3)OCO2
Scaffold Graph/Node level: C1OC2CCC(CC3COCC3CC3CCC4OCOC4C3)CC2O1
Scaffold Graph level: C1CC2CCC(CC3CCCC3CC3CCC4CCCC4C3)CC2C1
Functional groups: CO[C@H](O)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Furanoid lignans
ClassyFire Subclass: Tetrahydrofuran lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Dibenzylbutyrolactone lignans|Furanoid lignans
Synonymous chemical names:
Cubebin,(-), (-)cubebin, cubebin, (-)-cubebin, Cubebin,(-)-
External chemical identifiers:
CID:CID_117443; ChEMBL:CHEMBL399831; ChEBI:CHEBI:65684; ZINC:ZINC000004098754; FDASRS:J237078S8A; SureChEMBL:SCHEMBL4884683
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cubebin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 356.37
Log P RDKit 2.51
Topological polar surface area (Å2) RDKit 66.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Cubebin
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.908062
Cubebin
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 -6.07
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No