{[(2R,3S,4S,5R)-5-[2,4-dioxo-1,2,3,4-tetrahydro(2-13C,1,3-15N2)pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 160779
• Molecular Formular: C9H13N2O9P
• Molecular Mass: 327.16075363
• Monoisotopic Mass: 327.03329126
• SMILES: [C@@H]1(O)[C@@H](COP(=O)(O)O)O[C@H]([C@@H]1O)[15n]1ccc(=O)[15nH][13c]1=O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1[15n]1ccc(=O)[15nH][13c]1=O)COP(=O)(O)O
• InChI: InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7+,8-/m1/s1/i9+1,10+1,11+1
• InChIKey: DJJCXFVJDGTHFX-MXHOLXRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4S,5R)-5-[2,4-dioxo-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,4S,5R)-5-[2,4-dioxo(2-^1^3C,1,3-^1^5N₂)-3H-pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 1-(5-O-Phosphono-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione-13C,15N2; Uracil Arabinonucleoside-13C,15N2 5'-Phosphate; 1-β-D-Arabinofuranosyluracil-13C,15N2 5'-Monophosphate

Database IDs

• PubChem SID: 162254914
• PubChem CID: 71313476

CALCULATED PROPERTIES

• Acid pKa: 1.2255025
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.98036
• LogD (pH = 7.4): -6.070781
• Log P: -2.538808
• Molar Refractivity: 63.4385 cm^3
• Polarizability: 25.509138 Å^3
• Polar Surface Area: 165.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A764012

A labelled metablite of 1-β-D-Arabinofuranosyluracil.

REFERENCES

• Kozarich, J., et al.: Biochemistry, 12, 4458 (1973)
• Mueller, W. E.G., et al.: Cancer Res., 39, 1102 (1973)
• Haynie, S., et al.: Appl. Biochem. Biotechnol., 23, 205 (1973)
• Corfu, N., et al.: Eur. J. Biochem., 199, 659 (1973)
• Fischer, B., et al.: J. Med