etoposide   Click here for help

GtoPdb Ligand ID: 6815

Synonyms: (-)-etoposide | Etopophos® | Toposar® | trans-etoposide | VePesid® | VP 16-213 | VP-16
Approved drug PDB Ligand
etoposide is an approved drug (FDA (1983))
Compound class: Synthetic organic
Comment: A DNA topoisomerase II inhibitor which is a synthetic derivative of podophyllotoxin, found in the American Mayapple (Podophyllum peltatum).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 160.83
Molecular weight 588.18
XLogP 0.78
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)C
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)C
InChI InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
InChI Key VJJPUSNTGOMMGY-MRVIYFEKSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1983))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-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
3835 etoposide
Synonyms Click here for help
(-)-etoposide | Etopophos® | Toposar® | trans-etoposide | VePesid® | VP 16-213 | VP-16
Database Links Click here for help
CAS Registry No. 33419-42-0
ChEBI CHEBI:4911
ChEMBL Ligand CHEMBL44657
DrugBank Ligand DB00773
DrugCentral Ligand 1112
GtoPdb PubChem SID 178103421
PubChem CID 36462
RCSB PDB Ligand EVP
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Wikipedia Etoposide

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Tocris
Etoposide
Cat. No. 1226