IMPPAT Phytochemical information: 
Lignan

Lignan
Summary

SMILES: CCOC(=O)C1C(C)C(=O)c2c(C1c1cc(OC)c(c(c1)OC)OC)cc(c(c2)OC)OC
InChI: InChI=1S/C25H30O8/c1-8-33-25(27)21-13(2)23(26)16-12-18(29-4)17(28-3)11-15(16)22(21)14-9-19(30-5)24(32-7)20(10-14)31-6/h9-13,21-22H,8H2,1-7H3
InChIKey: PEIBIXYUYBVLDS-UHFFFAOYSA-N
DeepSMILES: CCOC=O)CCC)C=O)ccC6cccOC))ccc6)OC)))OC)))))))cccc6)OC)))OC
Scaffold Graph/Node/Bond level: O=C1CCC(c2ccccc2)c2ccccc21
Scaffold Graph/Node level: OC1CCC(C2CCCCC2)C2CCCCC12
Scaffold Graph level: CC1CCC(C2CCCCC2)C2CCCCC12
Functional groups: COC(C)=O; cC(=O)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Aryltetralin lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
lignan
External chemical identifiers:
CID:CID_261166; SureChEMBL:SCHEMBL30935
Chemical structure download


Lignan
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 458.51
Log P RDKit 3.87
Topological polar surface area (Å2) RDKit 89.52
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Lignan
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.55


Lignan
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.42
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