IMPPAT Phytochemical information: 
Dihydrocubebin
Dihydrocubebin
Summary

SMILES: OC[C@@H]([C@@H](Cc1ccc2c(c1)OCO2)CO)Cc1ccc2c(c1)OCO2
InChI: InChI=1S/C20H22O6/c21-9-15(5-13-1-3-17-19(7-13)25-11-23-17)16(10-22)6-14-2-4-18-20(8-14)26-12-24-18/h1-4,7-8,15-16,21-22H,5-6,9-12H2/t15-,16-/m0/s1
InChIKey: JKCVMTYNARDGET-HOTGVXAUSA-N
DeepSMILES: OC[C@@H][C@@H]Ccccccc6)OCO5)))))))))CO)))Ccccccc6)OCO5
Scaffold Graph/Node/Bond level: c1cc2c(cc1CCCCc1ccc3c(c1)OCO3)OCO2
Scaffold Graph/Node level: C(CCC1CCC2OCOC2C1)CC1CCC2OCOC2C1
Scaffold Graph level: C(CCC1CCC2CCCC2C1)CC1CCC2CCCC2C1
Functional groups: CO; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Dibenzylbutane lignans
ClassyFire Subclass: Dibenzylbutanediol lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans|Dibenzylbutane lignans
Synonymous chemical names:
(-)-dihydrocubebin, (-)dihydrocubebin, (-)-dihydro-cubebin, dihydrocubebin
External chemical identifiers:
CID:CID_193042; ChEMBL:CHEMBL486597; ChEBI:CHEBI:543841; ZINC:ZINC000000899938; SureChEMBL:SCHEMBL15775181
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Dihydrocubebin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 358.39
Log P RDKit 2.15
Topological polar surface area (Å2) RDKit 77.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
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 2
Stereochemical complexity RDKit 0.1
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 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Dihydrocubebin
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 Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.79
Dihydrocubebin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.42
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No