{[(2R,3S,4S,5R)-5-[4-amino-2-oxo-1,2-dihydro(4,5,6-13C3)pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 165328
• Molecular Formular: C9H14N3O8P
• Molecular Mass: 326.17448551
• Monoisotopic Mass: 326.06191557
• SMILES: [C@@H]1(O)[C@@H](COP(=O)(O)O)O[C@H]([C@@H]1O)n1[13cH][13cH][13c](nc1=O)N
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1[13cH][13cH][13c](nc1=O)N)COP(=O)(O)O
• InChI: InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7+,8-/m1/s1/i1+1,2+1,5+1
• InChIKey: IERHLVCPSMICTF-BOZZUQJYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4S,5R)-5-[4-amino-2-oxo-1,2-dihydro(4,5,6-^1^3C₃)pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,4S,5R)-5-[4-amino-2-oxo(4,5,6-^1^3C₃)pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 4-Amino-1-(5-O-phosphono-β-D-arabinofuranosyl)-2(1H)-pyrimidinone-13C3; 1-β-D-Arabinofuranosylcytosine-13C3 5'-Monophosphate; Cytosine-13C3 Arabinoside Monophosphate; NSC 99445-13C3; Cytarabine-13C3 5'-Monophosphate

Database IDs

• PubChem SID: 162259461
• PubChem CID: 71315150

CALCULATED PROPERTIES

• Acid pKa: 1.2485515
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -5.362575
• LogD (pH = 7.4): -6.4509172
• Log P: -3.1546948
• Molar Refractivity: 65.4177 cm^3
• Polarizability: 26.073345 Å^3
• Polar Surface Area: 175.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Base
• Apperance: White Solid
• Melting Point: 160-164°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C998107

A labelled derivative of Cytarabine, a potent cytotoxic-antiviral nucleoside.

REFERENCES

• Kufe, D., et al.: J. Biol. Chem., 255, 8997 (1980)
• Ross, D., et al.: Cancer Res., 50, 2658 (1980)
• Bhalla, K., et al.: Blood, 80, 2883 (1980)
• Tonetti, D., et al.: J. Biol. Chem., 269, 23230 (1980)