5-aza-4'-thio-2'-deoxycytidine
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]-1,3,5-triazin-2-one
Molecular Identity
5-aza-4'-thio-2'-deoxycytidine
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]-1,3,5-triazin-2-one
PubChem CID: 5270713
NTX-301 is 5-Aza-4'-thio-2'-deoxycytidine is an orally bioavailable, nucleoside analog and DNA methyltransferase I (DNMT1) inhibitor, with potential DNA hypomethylating and antineoplastic activities. Upon administration, 5-aza-4'-thio-2'-deoxycytidine (Aza-TdC) gets incorporated into DNA, where it binds to the active site of DNMT1, a maintenance methyltransferase that contributes to the hypermethylation and silencing of tumor suppressor genes. The formation of covalent DNMT1-DNA complexes inhibits DNMT1, prevents DNA methylation of CpG sites, causes CpG demethylation, and results in the re-expression and re-activation of silenced tumor suppressor genes. This inhibits tumor cell proliferation. DNMT1, overactivated in tumor cells, plays a key role in tumor cell proliferation.
2D Structure
Properties
C8H12N4O3S
Molecular Formula
244.27
Molecular Weight
g/mol
244.0630
Exact Mass
Da
-0.8
XLogP
Drug-like (Lipinski: < 5)
137
TPSA
Good oral absorption (< 140 A²)
3
H-Bond Donors
4
H-Bond Acceptors
359
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
5-aza-4'-thio-2'-deoxycytidine169514-76-55-Aza-t-dcydU2PTN0RZF6UNII-U2PTN0RZF6aza-TdCydNSC777586Aza-TdC5-Aza-TdCydRefChem:1020225-Aza-4-thio-2-deoxycytidine4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]-1,3,5-triazin-2-oneNTX-301orb2567189SCHEMBL19244084
Data from PubChem (NCBI)
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