IMPPAT Phytochemical information: 
Etoposide phosphate disodium salt
Etoposide phosphate disodium salt
Summary

SMILES: COc1cc(cc(c1OP(=O)([O-])[O-])OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@@H](c2c1cc1OCOc1c2)O[C@@H]1O[C@@H]2CO[C@H](O[C@H]2[C@@H]([C@H]1O)O)C.[Na+].[Na+]
InChI: InChI=1S/C29H33O16P.2Na/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35;;/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35);;/q;2*+1/p-2/t11-,15+,20-,21-,22+,23-,24-,25-,27-,29+;;/m1../s1
InChIKey: WCOHVOKFXMNYJU-XIYZZTPRSA-L
DeepSMILES: COcccccc6OP=O)[O-])[O-]))))OC))))[C@H][C@H]C=O)OC[C@@H]5[C@@H]cc9ccOCOc5c9)))))))))O[C@@H]O[C@@H]CO[C@H]O[C@H]6[C@@H][C@H]%10O))O))))C.[Na+].[Na+]
Scaffold Graph/Node/Bond level: O=C1OCC2C(OC3CCC4OCOCC4O3)c3cc4c(cc3C(c3ccccc3)C12)OCO4
Scaffold Graph/Node level: OC1OCC2C(OC3CCC4OCOCC4O3)C3CC4OCOC4CC3C(C3CCCCC3)C12
Scaffold Graph level: CC1CCC2C(CC3CCC4CCCCC4C3)C3CC4CCCC4CC3C(C3CCCCC3)C12
Functional groups: cOC; cOP(=O)([O-])[O-]; COC(=O)C; c1cOCO1; CO[C@@H](C)OC; CO; [Na+]
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan lactones
ClassyFire Subclass: Podophyllotoxins
Synonymous chemical names:
etopophos
External chemical identifiers:
CID:CID_6918091
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Etoposide phosphate disodium salt
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 712.51
Log P RDKit -6.15
Topological polar surface area (Å2) RDKit 213.02
Number of hydrogen bond acceptors RDKit 16
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 48
Number of heteroatoms RDKit 19
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.34
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Etoposide phosphate disodium salt
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 4
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 0.16
Etoposide phosphate disodium salt
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 -11.15
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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