topotecan   Click here for help

GtoPdb Ligand ID: 7101

Synonyms: Hycamtin® | SK-S-104864-A
Approved drug PDB Ligand
topotecan is an approved drug (EMA and FDA (1996))
Compound class: Synthetic organic
Comment: Topotecan is a semisynthetic analogue of the natural plant alkaloid camptothecin (PubChem CID 24360). Camptothecin was first isolated from the bark and stem of Camptotheca acuminata, the Chinsese happy tree. Topotecan is an anticancer drug which causes DNA strand breaks and leads to cell-cycle arrest and cell death.
Marketed formulations may contain topotecan hydrochloride (PubChem CID 60699).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 104.89
Molecular weight 421.16
XLogP 2.25
No. Lipinski's rules broken 0
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Canonical SMILES CCC1(O)C(=O)OCc2c1cc1c3nc4ccc(c(c4cc3Cn1c2=O)CN(C)C)O
Isomeric SMILES CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(c(c4cc3Cn1c2=O)CN(C)C)O
InChI InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1