IMPPAT Phytochemical information: 
Teniposide
Teniposide
Summary

SMILES: COc1cc(cc(c1O)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)c1cccs1
InChI: InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31+,32-/m0/s1
InChIKey: NRUKOCRGYNPUPR-QBPJDGROSA-N
DeepSMILES: COcccccc6O))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))))ccccs5
Scaffold Graph/Node/Bond level: O=C1OCC2C(OC3CCC4OC(c5cccs5)OCC4O3)c3cc4c(cc3C(c3ccccc3)C12)OCO4
Scaffold Graph/Node level: OC1OCC2C(OC3CCC4OC(C5CCCS5)OCC4O3)C3CC4OCOC4CC3C(C3CCCCC3)C12
Scaffold Graph level: CC1CCC2C(CC3CCC4CC(C5CCCC5)CCC4C3)C3CC4CCCC4CC3C(C3CCCCC3)C12
Functional groups: cOC; c[C@H](OC)OC; CO; cO; csc; COC(=O)C; c1cOCO1; CO[C@@H](C)OC
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:
vm-26
External chemical identifiers:
CID:CID_452548; ChEMBL:CHEMBL452231; ChEBI:CHEBI:75988; ZINC:ZINC000004099009; FDASRS:957E6438QA; SureChEMBL:SCHEMBL3908; MolPort-006-822-656
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Teniposide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 656.66
Log P RDKit 2.75
Topological polar surface area (Å2) RDKit 160.83
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 1
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 6
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 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 8
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 8
Teniposide
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.332796
Teniposide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.43
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
Teniposide
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000775ENSG00000091262ABCC6368ChEMBL
TAR_EXP_000773ENSG00000169083AR367ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000039ENSG00000125257ABCC410257BindingDB, ChEMBL, NPASS
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000405ENSG00000180210F22147ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000810ENSG00000128052KDR3791ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001056ENSG00000065989PDE4A5141ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_001618ENSG00000198900TOP17150ChEMBL, NPASS
TAR_EXP_001619ENSG00000131747TOP2A7153BindingDB, ChEMBL
TAR_EXP_001620ENSG00000077097TOP2B7155ChEMBL, NPASS
TAR_EXP_001808ENSG00000276582ABCB118647NPASS
TAR_EXP_001816ENSG00000108846ABCC38714BindingDB, ChEMBL, NPASS
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_000182ENSG00000023839ABCC21244NPASS
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL