IMPPAT Phytochemical information: 
meso-Secoisolariciresinol

meso-Secoisolariciresinol
Summary

SMILES: OC[C@H]([C@@H](Cc1ccc(c(c1)OC)O)CO)Cc1ccc(c(c1)OC)O
InChI: InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16+
InChIKey: PUETUDUXMCLALY-IYBDPMFKSA-N
DeepSMILES: OC[C@H][C@@H]Ccccccc6)OC)))O))))))CO)))Ccccccc6)OC)))O
Scaffold Graph/Node/Bond level: c1ccc(CCCCc2ccccc2)cc1
Scaffold Graph/Node level: C1CCC(CCCCC2CCCCC2)CC1
Scaffold Graph level: C1CCC(CCCCC2CCCCC2)CC1
Functional groups: CO; cOC; cO
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: Dibenzylbutane lignans
Synonymous chemical names:
meso-seco-isolariciresinol, meso-secoisolariciresinol
External chemical identifiers:
CID:CID_11552274; ZINC:ZINC000014694366
Chemical structure download


meso-Secoisolariciresinol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 362.42
Log P RDKit 2.12
Topological polar surface area (Å2) RDKit 99.38
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
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 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


meso-Secoisolariciresinol
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.545309


meso-Secoisolariciresinol
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 -6.72
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 No
P-glycoprotein substrate SwissADME Yes