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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Search Google for chemical match using the InChIKey NRUKOCRGYNPUPR-QBPJDGROSA-N
Search Google for chemicals with the same backbone NRUKOCRGYNPUPR
Search PubMed clinical trials teniposide
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UniChem Compound Search for chemical match using the InChIKey NRUKOCRGYNPUPR-QBPJDGROSA-N
UniChem Connectivity Search for chemical match using the InChIKey NRUKOCRGYNPUPR-QBPJDGROSA-N
Wikipedia Teniposide