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).
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: topotecan

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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
InChI Key UCFGDBYHRUNTLO-QHCPKHFHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA and FDA (1996))
International Nonproprietary Names Click here for help
INN number INN
6783 topotecan
Synonyms Click here for help
Hycamtin® | SK-S-104864-A
Database Links Click here for help
CAS Registry No. 123948-87-8
ChEBI CHEBI:63632
ChEMBL Ligand CHEMBL84
DrugBank Ligand DB01030
DrugCentral Ligand 2707
GtoPdb PubChem SID 178103679
PubChem CID 60700
RCSB PDB Ligand TTC
Search Google for chemical match using the InChIKey UCFGDBYHRUNTLO-QHCPKHFHSA-N
Search Google for chemicals with the same backbone UCFGDBYHRUNTLO
Search PubMed clinical trials topotecan
Search PubMed titles topotecan
Search PubMed titles/abstracts topotecan
UniChem Compound Search for chemical match using the InChIKey UCFGDBYHRUNTLO-QHCPKHFHSA-N
UniChem Connectivity Search for chemical match using the InChIKey UCFGDBYHRUNTLO-QHCPKHFHSA-N
Wikipedia topotecan