{[(2R,3S,5R)-4-fluoro-3-hydroxy-5-(5-iodo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 168916
• Molecular Formular: C9H11FIN2O8P
• Molecular Mass: 452.0688742
• Monoisotopic Mass: 451.92817817
• SMILES: n1([C@H]2C([C@H]([C@H](O2)COP(=O)(O)O)O)F)cc(c(=O)[nH]c1=O)I
• Canonical SMILES: O[C@H]1[C@@H](COP(=O)(O)O)O[C@H](C1F)n1cc(I)c(=O)[nH]c1=O
• InChI: InChI=1S/C9H11FIN2O8P/c10-5-6(14)4(2-20-22(17,18)19)21-8(5)13-1-3(11)7(15)12-9(13)16/h1,4-6,8,14H,2H2,(H,12,15,16)(H2,17,18,19)/t4-,5?,6+,8-/m1/s1
• InChIKey: PLIRJOIEMCOPIZ-TZLAVLDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,5R)-4-fluoro-3-hydroxy-5-(5-iodo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,5R)-4-fluoro-3-hydroxy-5-(5-iodo-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methoxyphosphonic acid
• Synonyms: Fialuridine 5'-Monophosphate; 1-(2-Deoxy-2-fluoro-5-O-phosphono-β-D-arabinofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione

Database IDs

• CAS Number: 99891-31-3
• PubChem SID: 162263048
• PubChem CID: 71316736

CALCULATED PROPERTIES

• Acid pKa: 1.2246214
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.1058393
• LogD (pH = 7.4): -4.335886
• Log P: -0.66203094
• Molar Refractivity: 75.0954 cm^3
• Polarizability: 30.182865 Å^3
• Polar Surface Area: 145.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F335010

Fialuridine 5’-Monophosphate (FIAUMP) is the phosphorylated derivative and major metabolite of the antiviral agent Fialuridine (F335000). Studies show that purified mammalian DNA polymerases were able to incorporate FIAUMP into the nascent DNA chain durin

REFERENCES

• McLaren, C. et al.: Int. Cong. Ser., 667, 57 (1985)
• Lewis, W. et al.: BIochem., 33, 14620 (1985)