IMPPAT Phytochemical information: 
Lignan P
Lignan P
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2[C@H]3COC(=O)[C@@H]3[C@@H](c3c2cc2OCOc2c3)c2cc(OC)c(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C27H30O13/c1-34-16-3-10(4-17(35-2)21(16)29)19-11-5-14-15(38-9-37-14)6-12(11)25(13-8-36-26(33)20(13)19)40-27-24(32)23(31)22(30)18(7-28)39-27/h3-6,13,18-20,22-25,27-32H,7-9H2,1-2H3/t13-,18+,19+,20-,22+,23-,24+,25+,27-/m0/s1
InChIKey: FOVRGQUEGRCWPD-BRLGUANISA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H][C@H]COC=O)[C@@H]5[C@@H]cc9ccOCOc5c9)))))))))cccOC))ccc6)OC)))O)))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1OCC2C(OC3CCCCO3)c3cc4c(cc3C(c3ccccc3)C12)OCO4
Scaffold Graph/Node level: OC1OCC2C(OC3CCCCO3)C3CC4OCOC4CC3C(C3CCCCC3)C12
Scaffold Graph level: CC1CCC2C(CC3CCCCC3)C3CC4CCCC4CC3C(C3CCCCC3)C12
Functional groups: CO; cO; CO[C@@H](C)OC; COC(=O)C; c1cOCO1; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan lactones
ClassyFire Subclass: Podophyllotoxins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
4'-demethylepipodophyllotoxin-beta-d-glucopyranoside
External chemical identifiers:
CID:CID_159949; ChEMBL:CHEMBL1778161; ZINC:ZINC000071341083; FDASRS:C2G3ZRK3U4
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lignan P
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 562.52
Log P RDKit -0.07
Topological polar surface area (Å2) RDKit 182.83
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
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
Lignan P
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 2
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.3
Lignan P
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.89
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes