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

• ChemBase ID: 160920
• Molecular Formular: C8H13N4O8P
• Molecular Mass: 324.184581
• Monoisotopic Mass: 324.04710003
• SMILES: [C@H]1(C([C@@H](O[C@@H]1COP(=O)(O)O)n1c(=O)nc(nc1)N)O)O
• Canonical SMILES: OC1[C@@H](O)[C@H](O[C@H]1n1cnc(nc1=O)N)COP(=O)(O)O
• InChI: InChI=1S/C8H13N4O8P/c9-7-10-2-12(8(15)11-7)6-5(14)4(13)3(20-6)1-19-21(16,17)18/h2-6,13-14H,1H2,(H2,9,11,15)(H2,16,17,18)/t3-,4+,5?,6-/m1/s1
• InChIKey: WODABQYEPQRZOS-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}phosphonic acid
• IUPAC Traditional name: [(2R,3R,5R)-5-(4-amino-2-oxo-1,3,5-triazin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 4-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; 4-Amino-1-β-D-ribofuranosyl- s-triazin-2(1H)-one 5'-Phosphate; 5-Azacytidine 5'-Monophosphate 60%

Database IDs

• CAS Number: 2226-72-4
• PubChem SID: 162255055
• PubChem CID: 46780500

CALCULATED PROPERTIES

• Acid pKa: 1.2353263
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -5.6303024
• LogD (pH = 7.4): -6.7187343
• Log P: -3.344024
• Molar Refractivity: 63.0661 cm^3
• Polarizability: 25.322441 Å^3
• Polar Surface Area: 187.5 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: >127°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A796020

A metabolite of 5-Azacytidine. This compound contains sodium chloride and water.

REFERENCES

• Lee, T., et al.: Cancer Res., 34, 2482 ( (1974)
• Drake, J.C., et al.: Biochem. Pharmacol., 29, 807 (1974)