Secondary metabolite: 4-Hydroxysesamin



4-Hydroxysesamin
Summary
Molecular formula: C20H18O7
SMILES: OC1O[C@H]([C@H]2[C@@H]1[C@@H](OC2)c1ccc2c(c1)OCO2)c1ccc2c(c1)OCO2
InChI: InChI=1S/C20H18O7/c21-20-17-12(18(27-20)10-1-3-13-15(5-10)25-8-23-13)7-22-19(17)11-2-4-14-16(6-11)26-9-24-14/h1-6,12,17-21H,7-9H2/t12-,17-,18+,19+,20?/m1/s1
InChIKey: AWLJZFUREZNLGG-RXABKWRFSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lignans, neolignans and related compounds
Class: Furanoid lignans
Synonymous chemical names:
4-hydroxysesamin
Chemical structure download



4-Hydroxysesamin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 370.36
Log P RDKit 2.54
Topological polar surface area (Å2) RDKit 75.61
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 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 8
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.4
Shape complexity RDKit 0.4
Number of rotatable bonds SwissADME 2
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



4-Hydroxysesamin
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
Egan filter RDKit Good
Pfizer’s 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.87



4-Hydroxysesamin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.03
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 No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No




Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo