capecitabine   Click here for help

GtoPdb Ligand ID: 6799

Synonyms: Ro-09-1978-000 | Ro-091978000 | Xeloda®
Approved drug
capecitabine is an approved drug (FDA (1998), EMA (2001))
Compound class: Synthetic organic
Comment: Capecitabine is a prodrug, that is enzymatically converted to 5-fluorouracil (active agent). It is a thymidylate synthase inhibitor.

capecitabine is commercially available from our sponsors

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 CDK toolkit. 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 8
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 122.91
Molecular weight 359.15
XLogP 2.04
No. Lipinski's rules broken 0
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.

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Canonical SMILES CCCCCOC(=O)Nc1nc(=O)n(cc1F)C1OC(C(C1O)O)C
Isomeric SMILES CCCCCOC(=O)Nc1nc(=O)n(cc1F)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C
InChI InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1
InChI Key GAGWJHPBXLXJQN-UORFTKCHSA-N
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
thymidylate synthetase Primary target of this compound Hs Inhibitor Inhibition - - - 1-2
⤷ [1-2]
Targets where the ligand is described in the comment field
Target Comment
dihydropyrimidine dehydrogenase Dihydropyrimidine dehydrogenase is required for the first and rate-limiting step of pyrimidine catabolism. In addition to degrading pyrimidines, it also breaks down pyrimidine-based 5-fluorouracil, the anticancer cytostatic agent that is produced from chemotherapeutic prodrugs including capecitabine and tegafur.