azacitidine   

GtoPdb Ligand ID: 6796

Synonyms: 5-AZAC | 5-azacytidine | ladakamycin | U-18496 | Vidaza®
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.
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2004), EMA (2009))
IUPAC Name
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
International Nonproprietary Names
INN number INN
4520 azacitidine
Synonyms
5-AZAC | 5-azacytidine | ladakamycin | U-18496 | Vidaza®
Database Links
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
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Wikipedia Azacitidine

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Tocris
5-Azacytidine
Cat. No. 3842