IMPPAT Phytochemical information: 
Podophyllotoxin glucoside
Podophyllotoxin glucoside
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)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C28H32O13/c1-34-17-4-11(5-18(35-2)26(17)36-3)20-12-6-15-16(39-10-38-15)7-13(12)25(14-9-37-27(33)21(14)20)41-28-24(32)23(31)22(30)19(8-29)40-28/h4-7,14,19-25,28-32H,8-10H2,1-3H3/t14-,19+,20+,21-,22+,23-,24+,25-,28-/m0/s1
InChIKey: NXVJTGLCCSFGAT-QNDDJFOYSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H][C@H]COC=O)[C@@H]5[C@@H]cc9ccOCOc5c9)))))))))cccOC))ccc6)OC)))OC))))))))))))))[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; cOC; CO[C@@H](C)OC; COC(=O)C; c1cOCO1
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:
podophyllotoxin-β-d-glucoside
External chemical identifiers:
CID:CID_161177; ChEMBL:CHEMBL503644; ZINC:ZINC000042803835; SureChEMBL:SCHEMBL2825043
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Podophyllotoxin glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 576.55
Log P RDKit 0.23
Topological polar surface area (Å2) RDKit 171.83
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 41
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 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 7
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
Podophyllotoxin glucoside
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 3
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 0.33
Podophyllotoxin glucoside
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 -9.52
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 No
P-glycoprotein substrate SwissADME Yes