[3,4-Diacetyloxy-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)oxolan-2-yl]methyl acetate
Basic information
- CAS
10302-78-0- Standard SMILES
CC(=O)OCC1OC(n2cnc(N)nc2=O)C(OC(C)=O)C1OC(C)=O- InChIKey
OTQJVHISAFFLMA-UHFFFAOYSA-N- Molecular formula
- C14H18N4O8
- Average molar mass
- 370.31 g/mol
- Monoisotopic mass
- 370.11246355
Names & identifiers
- Preferred name
- [3,4-Diacetyloxy-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)oxolan-2-yl]methyl acetate
- IUPAC
- [3,4-diacetyloxy-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)oxolan-2-yl]methyl acetate
- English name
- 2'',3'',5''-Triacetyl -azacytidine
- Molecular formula
- C14H18N4O8
- Molecular weight
- 370.32
Names & synonyms
10302-78-0NSC291930[3,4-diacetyloxy-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)oxolan-2-yl]methyl acetate2',3',5'-triacetyl-5-AzacytidineSCHEMBL13243124DTXSID30908161AKOS040759276NSC-291930DA-49246s-Triazin-2(1H)-one, triacetate (ester)[3,4-diacetoxy-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)tetrahydrofuran-2-yl]methyl acetate1,5-Triazin-2(1H)-one, 4-amino-1-(2,3,5-tri-O-acetyl-.beta.-D-ribofuranosyl)-
Show more names
-O-triacetateTriacetyl azacitidineAzacitidine TriacetateAzacitidine Impurity 48Intermediate of Azacitidine2'3'5'-triacetyl-5-Azacytosine2',3',5'-Tri-O-Acetyl-Azacytidine2'',3'',5''-Triacetyl -azacytidine
4-Imino-1-(2,3,5-tri-O-acetylpentofuranosyl)-1,4-dihydro-1,3,5-triazin-2-ol[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)oxolan-2-yl]methyl acetate
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 159 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 8
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 676
Physicochemical properties
- Boiling point
- 497.3 · 497.3±55.0 °C(Predicted)
- Density
- 1.6 · 1.60±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 30 mg/ml · ≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
- form
- crystalline solid
- pka
- 3.06 · 3.06±0.20(Predicted)
- Appearance
- White to off-white Solid
- InChI
- InChI=1/C14H18N4O8/c1-6(19)23-4-9-10(24-7(2)20)11(25-8(3)21)12(26-9)18-5-16-13(15)17-14(18)22/h5,9-12H,4H2,1-3H3,(H2,15,17,22)/t9-,10-,11-,12-/s3
- InChIKey
- OTQJVHISAFFLMA-IOCWGDCUNA-N
- SMILES
- [C@H]1(O[C@@H]([C@@H](OC(C)=O)[C@H]1OC(=O)C)COC(C)=O)N1C(=O)N=C(N)N=C1 |&1:0,2,3,8,r|
- CAS DataBase Reference
- 10302 · 10302-78-0
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
Description5-Azacytidine is an inhibitor of DNA methyltransferase, potentially serving to reverse epigenetic changes. It reduces hypermethylation associated with certain diseases, including myelodysplastic syndromes and cancer. 2’,3’,5’-triacetyl-5-Azacytidine is a prodrug form of 5-azacytidine that may be rapidly absorbed orally without formation of major metabolites in the gastrointestinal tract.
Uses5-Azacytidine is an inhibitor of DNA methyltransferaes, potentially serving to reverse epigenetic changes. It reduces hypermethylation associated with certain diseases, including myelodysplastic syndromes and cancer. 2’,3’,5’-triacetyl-5-Azacytidine is a prodrug form of 5-azacytidine that may be rapidly absorbed orally without formation of major metabolites in the gastrointestinal tract.[Cayman Chemical]
Upstream & downstream products
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