teniposide   Click here for help

GtoPdb Ligand ID: 6843

Synonyms: isosulfan blue | VM-26 | Vumon®
Approved drug PDB Ligand
teniposide is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: A podophyllotoxin derivative which achieves cytotoxicity by inhibiting type II topoisomerase activity. Many (85) isomeric alternatives for this compound are listed on PubChem. Click here to link directly to the PubChem listing. The structure shown here matches that shown in the INN document for this compound.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 189.07
Molecular weight 656.16
XLogP 1.19
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc(cc(c1O)OC)C1C2C(=O)OCC2C(c2c1cc1OCOc1c2)OC1OC2COC(OC2C(C1O)O)c1cccs1
Isomeric 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
InChI Key NRUKOCRGYNPUPR-QBPJDGROSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1992))
IUPAC Name Click here for help
(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
International Nonproprietary Names Click here for help
INN number INN
3836 teniposide
Synonyms Click here for help
isosulfan blue | VM-26 | Vumon®
Database Links Click here for help
CAS Registry No. 29767-20-2
ChEBI CHEBI:75988
ChEMBL Ligand CHEMBL452231
DrugBank Ligand DB00444
DrugCentral Ligand 2590
GtoPdb PubChem SID 178103449
PubChem CID 452548
RCSB PDB Ligand 9TP
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Wikipedia Teniposide