IMPPAT Phytochemical information: 
Picropodopyllotoxone
Picropodopyllotoxone
Summary

SMILES: COc1cc(cc(c1OC)OC)[C@H]1[C@@H]2C(=O)OC[C@@H]2C(=O)c2c1cc1OCOc1c2
InChI: InChI=1S/C22H20O8/c1-25-16-4-10(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/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18+,19+/m0/s1
InChIKey: ISCQYPPCSYRZOT-MJXNMMHHSA-N
DeepSMILES: COcccccc6OC)))OC))))[C@H][C@@H]C=O)OC[C@@H]5C=O)cc9ccOCOc5c9
Scaffold Graph/Node/Bond level: O=C1c2cc3c(cc2C(c2ccccc2)C2C(=O)OCC12)OCO3
Scaffold Graph/Node level: OC1OCC2C(O)C3CC4OCOC4CC3C(C3CCCCC3)C12
Scaffold Graph level: CC1CCC2C(C)C3CC4CCCC4CC3C(C3CCCCC3)C12
Functional groups: cOC; COC(=O)C; cC(=O)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan lactones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
picropodophyllone
External chemical identifiers:
CID:CID_3083574; ChEMBL:CHEMBL82303; ZINC:ZINC000026489484; SureChEMBL:SCHEMBL18381519
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Picropodopyllotoxone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 412.39
Log P RDKit 2.56
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 22
Number of heavy atoms RDKit 30
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 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Picropodopyllotoxone
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 0.708217
Picropodopyllotoxone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -7.03
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No