IMPPAT Phytochemical information: 
Dihydrosesamin

Dihydrosesamin
Summary

SMILES: OC[C@H]1[C@H](CO[C@@H]1c1ccc2c(c1)OCO2)Cc1ccc2c(c1)OCO2
InChI: InChI=1S/C20H20O6/c21-8-15-14(5-12-1-3-16-18(6-12)25-10-23-16)9-22-20(15)13-2-4-17-19(7-13)26-11-24-17/h1-4,6-7,14-15,20-21H,5,8-11H2/t14-,15-,20+/m0/s1
InChIKey: JOCPSXXUQJXDBI-AUSJPIAWSA-N
DeepSMILES: OC[C@H][C@H]CO[C@@H]5cccccc6)OCO5)))))))))))Ccccccc6)OCO5
Scaffold Graph/Node/Bond level: c1cc2c(cc1CC1COC(c3ccc4c(c3)OCO4)C1)OCO2
Scaffold Graph/Node level: C1OC2CCC(CC3COC(C4CCC5OCOC5C4)C3)CC2O1
Scaffold Graph level: C1CC2CCC(CC3CCC(C4CCC5CCCC5C4)C3)CC2C1
Functional groups: CO; COC; 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: Furanoid lignans
Synonymous chemical names:
dihydrosesamin
External chemical identifiers:
CID:CID_10871980; ChEMBL:CHEMBL1079706; ZINC:ZINC000014642046
Chemical structure download


Dihydrosesamin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 356.37
Log P RDKit 2.68
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


Dihydrosesamin
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 0.908607


Dihydrosesamin
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.49
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No