IMPPAT Phytochemical information: 
Podophyllinic acid
Podophyllinic acid
Summary

SMILES: OC[C@@H]1[C@@H](O)c2cc3OCOc3cc2[C@H]([C@H]1C(=O)O)c1cc(OC)c(c(c1)OC)OC
InChI: InChI=1S/C22H24O9/c1-27-16-4-10(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/h4-7,13,18-20,23-24H,8-9H2,1-3H3,(H,25,26)/t13-,18+,19-,20-/m0/s1
InChIKey: XRBSKUSTLXISAB-XVVDYKMHSA-N
DeepSMILES: OC[C@@H][C@@H]O)cccOCOc5cc9[C@H][C@H]%13C=O)O)))cccOC))ccc6)OC)))OC
Scaffold Graph/Node/Bond level: c1ccc(C2CCCc3cc4c(cc32)OCO4)cc1
Scaffold Graph/Node level: C1CCC(C2CCCC3CC4OCOC4CC32)CC1
Scaffold Graph level: C1CCC(C2CCCC3CC4CCCC4CC32)CC1
Functional groups: CO; c1cOCO1; CC(=O)O; 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:
2,3-trans-picropodophyllinic acid, podophyllic acid, podophyllinic acid
External chemical identifiers:
CID:CID_134632; ChEMBL:CHEMBL32955; FDASRS:16FK9L3306; SureChEMBL:SCHEMBL8016
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Podophyllinic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 432.43
Log P RDKit 1.93
Topological polar surface area (Å2) RDKit 123.91
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.41
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Podophyllinic acid
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.628004
Podophyllinic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -7.56
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