IMPPAT Phytochemical information: 
(+)-Episesaminone

(+)-Episesaminone
Summary

SMILES: OC[C@@H]1[C@H](OC[C@@H]1C(=O)c1ccc2c(c1)OCO2)c1ccc2c(c1)OCO2
InChI: InChI=1S/C20H18O7/c21-7-13-14(19(22)11-1-3-15-17(5-11)26-9-24-15)8-23-20(13)12-2-4-16-18(6-12)27-10-25-16/h1-6,13-14,20-21H,7-10H2/t13-,14-,20+/m0/s1
InChIKey: RZIWMSJDPYUACC-PJSUUKDQSA-N
DeepSMILES: OC[C@@H][C@H]OC[C@@H]5C=O)cccccc6)OCO5))))))))))))cccccc6)OCO5
Scaffold Graph/Node/Bond level: O=C(c1ccc2c(c1)OCO2)C1COC(c2ccc3c(c2)OCO3)C1
Scaffold Graph/Node level: OC(C1COC(C2CCC3OCOC3C2)C1)C1CCC2OCOC2C1
Scaffold Graph level: CC(C1CCC2CCCC2C1)C1CCC(C2CCC3CCCC3C2)C1
Functional groups: CO; COC; cC(C)=O; 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:
(+)-episesaminone
External chemical identifiers:
CID:CID_10523159; ZINC:ZINC000014435830
Chemical structure download


(+)-Episesaminone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 370.36
Log P RDKit 2.32
Topological polar surface area (Å2) RDKit 83.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
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 3
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.35
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


(+)-Episesaminone
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 0.83


(+)-Episesaminone
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 -7.19
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