(2S,3S,4S,5R,6R)-6-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169269
• Molecular Formular: C10H11FN2O8
• Molecular Mass: 306.2013432
• Monoisotopic Mass: 306.04994354
• SMILES: [nH]1c(=O)c(cn(c1=O)[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)F
• Canonical SMILES: OC(=O)[C@@H]1O[C@H]([C@H]([C@H]([C@@H]1O)O)O)n1cc(F)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H11FN2O8/c11-2-1-13(10(20)12-7(2)17)8-5(16)3(14)4(15)6(21-8)9(18)19/h1,3-6,8,14-16H,(H,18,19)(H,12,17,20)/t3-,4-,5+,6-,8+/m0/s1
• InChIKey: LKZGKOYOKVWGFN-UQGZVRACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-(5-fluoro-2,4-dioxo-3H-pyrimidin-1-yl)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-Deoxy-1-(5-fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-glucopyranuronic Acid; 5-Fluoro-1-(β-D-glucuronopyranosyl)uracil; 5-Fluorouracil N-β-D-Glucuronide

Database IDs

• CAS Number: 66048-45-1
• PubChem SID: 162263401
• PubChem CID: 125224

CALCULATED PROPERTIES

• Acid pKa: 3.346144
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.667684
• LogD (pH = 7.4): -6.1243415
• Log P: -2.5258596
• Molar Refractivity: 58.5984 cm^3
• Polarizability: 23.38715 Å^3
• Polar Surface Area: 156.63 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F596010

5-Fluorouracil N-β-D-Glucuronide is the N-glucuronide derivative of 5-Fluorouracil (F596010). 5-Fluorouracil N-β-D-Glucuronide unlike its O-glucuronide analog does not possess significant antitumor activity.

REFERENCES

• Baba, T. et al.: Gann, 69, 283 (1978)
• Kaneko, M. et al.: Nucleic Acid Res., 3, 35 (1978)