[({[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydro-1,3,5-triazin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

• ChemBase ID: 160919
• Molecular Formular: C8H14N4O11P2
• Molecular Mass: 404.164482
• Monoisotopic Mass: 404.01343055
• SMILES: [C@H]1(C([C@@H](O[C@@H]1COP(=O)(OP(=O)(O)O)O)n1c(=O)nc(nc1)N)O)O
• Canonical SMILES: O[C@H]1[C@@H](COP(=O)(OP(=O)(O)O)O)O[C@H](C1O)n1cnc(nc1=O)N
• InChI: InChI=1S/C8H14N4O11P2/c9-7-10-2-12(8(15)11-7)6-5(14)4(13)3(22-6)1-21-25(19,20)23-24(16,17)18/h2-6,13-14H,1H2,(H,19,20)(H2,9,11,15)(H2,16,17,18)/t3-,4+,5?,6-/m1/s1
• InChIKey: RQKDGRDHJHINET-WGDKFINWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydro-1,3,5-triazin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
• IUPAC Traditional name: {[(2R,3R,5R)-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
• Synonyms: 4-Amino-1-[5-O-[hydroxy(phosphonooxy)phosphinyl]-β-D-ribofuranosyl]-1,3,5-triazin-2(1H)-one; 4-Amino-1-β-D-ribofuranosyl-s-triazin-2(1H)-one 5'-Pyrophosphate; 5-Azacitidine 5'-Diphosphate; 5-Azacytidine 5'-Diphosphate

Database IDs

• CAS Number: 2226-73-5
• PubChem SID: 162255054
• PubChem CID: 71313540

CALCULATED PROPERTIES

• Acid pKa: 1.7752383
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -8.013594
• LogD (pH = 7.4): -8.644699
• Log P: -3.6106975
• Molar Refractivity: 73.939 cm^3
• Polarizability: 30.129515 Å^3
• Polar Surface Area: 234.03 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A796015

5-Azacytidine 5'-Diphosphate is a phosphorylated metabolite of 5-Azacytidine (A796000).

REFERENCES

• Jurovcik, M. et al.: Coll. Czech. Chem. Comm., 30, 3370 (1965)