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(S)-DRF-1042   Click here for help

GtoPdb Ligand ID: 8261

Synonyms: 5(S)-(2'-hydroxyethoxy)-20(S)-camptothecin | 5(S)-(2'-hydroxyethoxy)-20(S)-CPT
Compound class: Synthetic organic
Comment: S-isomer of DRF-1042 is a derivative of camptothecin, a natural quinoline alkaloid with cytotoxic effects, which acts to inhibit DNA topoisomerase I. This compound only contains the (S) stereoisomer, as described in patent US20110177161 [1]. PubChem CID 23631031 represents the molecule with no specified stereochemistry at the 5 position.
Two camptothecin derivatives are already approved for clinical use: topotecan and irinotecan.
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 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.

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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 110.88
Molecular weight 408.13
XLogP 1.8
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
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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.

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/)

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Canonical SMILES OCCOC1c2cc3ccccc3nc2c2n1c(=O)c1c(c2)CC(C(=O)O1)(O)CC
Isomeric SMILES OCCO[C@H]1c2cc3ccccc3nc2c2n1c(=O)c1c(c2)C[C@@](C(=O)O1)(O)CC
InChI InChI=1S/C22H20N2O6/c1-2-22(28)11-13-10-16-17-14(9-12-5-3-4-6-15(12)23-17)20(29-8-7-25)24(16)19(26)18(13)30-21(22)27/h3-6,9-10,20,25,28H,2,7-8,11H2,1H3/t20-,22-/m0/s1
InChI Key UPAYPYZHFCRCMO-UNMCSNQZSA-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/)
References
1. Nekkanti VK, Karatgi PJ, Paithankar M, Pillai RS, Venkateswarlu A, Shanvas A, Kumar RA, Ramesh M, Raju S, Subrahmanyam D et al.. (2011)
Pharmaceutical compositions of [5(s)-(2'-hydroxyethoxy)-20(s)-camptothecin.
Patent number: US20110177161. Assignee: Dr. Reddy's Laboratories Limited,. Priority date: 24/05/2007. Publication date: 21/07/2011.