decitabine   

GtoPdb Ligand ID: 6805

Synonyms: 5-azadeoxycytidine | ASTX-727 | ASTX727 (decitabine + cedazuridine) | azadC | DAC | Dacogen® | Inqovi® (decitabine + cedazuridine)
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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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
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Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel