IMPPAT Phytochemical information: 
Podophyllin
Podophyllin
Summary

SMILES: OCC1C(O)c2cc3OCOc3cc2C(C1C(=O)O)c1cc(OC)c(c(c1)OC)OC.OCC1C(O)c2cc3OCOc3cc2C(C1C(=O)O)c1cc(OC)c(c(c1)OC)OC.COc1cc(cc(c1OC)OC)C1C2C(=O)OCC2C(c2c1cc1OCOc1c2)O.COc1cc(cc(c1OC)OC)C1C2C(=O)OCC2C(c2c1cc1OCOc1c2)O
InChI: InChI=1S/2C22H24O9.2C22H22O8/c2*1-27-16-4-10(5-17(28-2)21(16)29-3)18-11-6-14-15(31-9-30-14)7-12(11)20(24)13(8-23)19(18)22(25)26;2*1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h2*4-7,13,18-20,23-24H,8-9H2,1-3H3,(H,25,26);2*4-7,13,18-20,23H,8-9H2,1-3H3
InChIKey: KOUZYZCESNTXJO-UHFFFAOYSA-N
DeepSMILES: OCCCO)cccOCOc5cc9CC%13C=O)O)))cccOC))ccc6)OC)))OC.OCCCO)cccOCOc5cc9CC%13C=O)O)))cccOC))ccc6)OC)))OC.COcccccc6OC)))OC))))CCC=O)OCC5Ccc9ccOCOc5c9)))))))))O.COcccccc6OC)))OC))))CCC=O)OCC5Ccc9ccOCOc5c9)))))))))O
Functional groups: CC(=O)O; CO; COC(C)=O; c1cOCO1; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Aryltetralin lignans
ClassyFire Subclass: 9,9p-dihydroxyaryltetralin lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
podophyllin
External chemical identifiers:
CID:11979494; MolPort-046-703-409
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Podophyllin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1693.67
Log P RDKit 8.68
Topological polar surface area (Å2) RDKit 433.18
Number of hydrogen bond acceptors RDKit 32
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 88
Number of heavy atoms RDKit 122
Number of heteroatoms RDKit 34
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 16
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 52
Number of sp3 hybridized carbon atoms RDKit 36
Shape complexity RDKit 0.41
Number of rotatable bonds RDKit 20
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 6
Number of aliphatic rings RDKit 10
Number of aromatic carbocycles RDKit 8
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 8
Total number of rings RDKit 18
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 18
Podophyllin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 4
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0331