etoposide   

GtoPdb Ligand ID: 6815

Synonyms: (-)-etoposide | Etopophos® | Toposar® | trans-etoposide | VePesid® | VP 16-213 | VP-16
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).
2D Structure
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Physico-chemical Properties
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
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
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
(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
INN number INN
3835 etoposide
Synonyms
(-)-etoposide | Etopophos® | Toposar® | trans-etoposide | VePesid® | VP 16-213 | VP-16
Database Links
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