IMPPAT Phytochemical information: 
Sesamolin
Sesamolin
Summary

SMILES: C1Oc2c(O1)cc(cc2)O[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc2c(c1)OCO2
InChI: InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
InChIKey: ZZMNWJVJUKMZJY-AFHBHXEDSA-N
DeepSMILES: COccO5)cccc6))O[C@H]OC[C@H][C@@H]5CO[C@@H]5cccccc6)OCO5
Scaffold Graph/Node/Bond level: c1cc2c(cc1OC1OCC3C(c4ccc5c(c4)OCO5)OCC13)OCO2
Scaffold Graph/Node level: C1OC2CCC(OC3OCC4C3COC4C3CCC4OCOC4C3)CC2O1
Scaffold Graph level: C1CC2CCC(CC3CCC4C3CCC4C3CCC4CCCC4C3)CC2C1
Functional groups: c1cOCO1; cO[C@H](C)OC; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzodioxoles
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Furofuranoid lignans
Synonymous chemical names:
2-(3,4-methylenedioxyphenoxy)-6(3,4-methylenedioxyphenyl)-cis-3 7-dioxabicyclo-(3.3.0)-octane (sesamolin), Sesamolin, sesamolin, (+)-sesamolin
External chemical identifiers:
CID:CID_101746; ChEMBL:CHEMBL2059646; ChEBI:CHEBI:175751; ZINC:ZINC000006094187; FDASRS:7A90TJ149G; SureChEMBL:SCHEMBL163696; MolPort-020-005-858
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Sesamolin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 370.36
Log P RDKit 2.88
Topological polar surface area (Å2) RDKit 64.61
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.2
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 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Sesamolin
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 0.82309
Sesamolin
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 -6.44
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
Sesamolin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000311032CASP3800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.