(2S,3S,4S,5R,6R)-6-[5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro(2-13C,1,3-15N2)pyrimidin-1-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169270
• Molecular Formular: C10H11FN2O8
• Molecular Mass: 309.18081583
• Monoisotopic Mass: 309.04736817
• SMILES: [15nH]1c(=O)c(c[15n]([13c]1=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)[15n]1cc(F)c(=O)[15nH][13c]1=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/i10+1,12+1,13+1
• InChIKey: LKZGKOYOKVWGFN-LFHIAGTDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[5-fluoro-2,4-dioxo-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[5-fluoro-2,4-dioxo(2-^1^3C,1,3-^1^5N₂)-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-13C,15N2; 5-Fluoro-1-(β-D-glucuronopyranosyl)uracil-13C,15N2; 5-Fluorouracil-13C,15N2 N-β-D-Glucuronide

Database IDs

• PubChem SID: 162263402
• PubChem CID: 71316885

CALCULATED PROPERTIES

• Polarizability: 23.38715 Å^3
• Polar Surface Area: 156.63 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• 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

DETAILS

Toronto Research Chemicals - F596012

Labelled 5-Fluorouracil N-β-D-Glucuronide, 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)