decitabine   Click here for help

GtoPdb Ligand ID: 6805

Synonyms: 5-azadeoxycytidine | ASTX-727 | ASTX727 (decitabine + cedazuridine) | azadC | DAC | Dacogen® | Inqovi® (decitabine + cedazuridine)
Approved drug
decitabine is an approved drug (FDA (2006), EMA (2012))
Compound class: Synthetic organic
Comment: DNA methylation inhibitor and RNA inhibitor. Like azacitidine, decitabine inhibits DNA methylation in vitro [1], but not by directly interacting with methyltransferase enzymes.
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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Click here for structure editor
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 7
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 123.49
Molecular weight 228.09
XLogP -1.21
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 OCC1OC(CC1O)n1cnc(nc1=O)N
Isomeric SMILES OC[C@H]1O[C@H](C[C@@H]1O)n1cnc(nc1=O)N
InChI InChI=1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1
InChI Key XAUDJQYHKZQPEU-KVQBGUIXSA-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 (FDA (2006), EMA (2012))
IUPAC Name Click here for help
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
International Nonproprietary Names Click here for help
INN number INN
6374 decitabine
Synonyms Click here for help
5-azadeoxycytidine | ASTX-727 | ASTX727 (decitabine + cedazuridine) | azadC | DAC | Dacogen® | Inqovi® (decitabine + cedazuridine)
Database Links Click here for help
CAS Registry No. 2353-33-5
ChEBI CHEBI:50131
ChEMBL Ligand CHEMBL1201129
DrugBank Ligand DB01262
DrugCentral Ligand 790
GtoPdb PubChem SID 178103411
PubChem CID 451668
Search Google for chemical match using the InChIKey XAUDJQYHKZQPEU-KVQBGUIXSA-N
Search Google for chemicals with the same backbone XAUDJQYHKZQPEU
Search PubMed clinical trials decitabine
Search PubMed titles decitabine
Search PubMed titles/abstracts decitabine
UniChem Compound Search for chemical match using the InChIKey XAUDJQYHKZQPEU-KVQBGUIXSA-N
UniChem Connectivity Search for chemical match using the InChIKey XAUDJQYHKZQPEU-KVQBGUIXSA-N
Wikipedia Decitabine