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azacitidine   Click here for help

GtoPdb Ligand ID: 6796

Synonyms: 5-AZAC | 5-azacytidine | ladakamycin | Onureg® | Onureg® (CC-486; oral azacitidine) | U-18496 | Vidaza®
Approved drug PDB Ligand Immunopharmacology Ligand
azacitidine is an approved drug (FDA (2004), EMA (2009))
Compound class: Synthetic organic
Comment: DNA methyltransferase and RNA inhibitor. Azacitidine inhibits DNA methylation in vitro [3], but not by directly interacting with the methyltransferase enzyme DNMT1.

azacitidine 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 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 8
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 143.72
Molecular weight 244.08
XLogP -1.81
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(C(C1O)O)n1cnc(nc1=O)N
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc(nc1=O)N
InChI InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
InChI Key NMUSYJAQQFHJEW-KVTDHHQDSA-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. US FDA (2004)  |  EU EMA (2009)
IUPAC Name Click here for help
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
International Nonproprietary Names Click here for help
INN number INN
4520 azacitidine
Synonyms Click here for help
5-AZAC | 5-azacytidine | ladakamycin | Onureg® | Onureg® (CC-486; oral azacitidine) | U-18496 | Vidaza®
Database Links Click here for help
CAS Registry No. 320-67-2
ChEBI CHEBI:2038
ChEMBL Ligand CHEMBL1489
DrugBank Ligand DB00928
DrugCentral Ligand 25
GtoPdb PubChem SID 178103402
PubChem CID 9444
RCSB PDB Ligand 5AE
Search Google for chemical match using the InChIKey NMUSYJAQQFHJEW-KVTDHHQDSA-N
Search Google for chemicals with the same backbone NMUSYJAQQFHJEW
Search PubMed clinical trials azacitidine
Search PubMed titles azacitidine
Search PubMed titles/abstracts azacitidine
UniChem Compound Search for chemical match using the InChIKey NMUSYJAQQFHJEW-KVTDHHQDSA-N
UniChem Connectivity Search for chemical match using the InChIKey NMUSYJAQQFHJEW-KVTDHHQDSA-N
Wikipedia Azacitidine

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MedChemExpress
5-Azacytidine (links to external site)
Cat. No. HY-10586