({[({[(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

• ChemBase ID: 164864
• Molecular Formular: C10H14ClFN5O12P3
• Molecular Mass: 543.6171462
• Monoisotopic Mass: 542.9524367
• SMILES: n1c(nc2c(c1N)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(OP(=O)(O)OP(=O)(O)O)O)O)F)Cl
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)O)O)O)O[C@H]([C@@H]1F)n1cnc2c1nc(Cl)nc2N
• InChI: InChI=1S/C10H14ClFN5O12P3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(18)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-4,6,9,18H,1H2,(H,22,23)(H,24,25)(H2,13,15,16)(H2,19,20,21)/t3-,4+,6-,9-/m1/s1
• InChIKey: ILZCVFJUTWHERD-AYQXTPAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
• IUPAC Traditional name: ({[(2R,3R,4S,5R)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
• Synonyms: 2-Chloro-9-[2-deoxy-2-fluoro-5-O-[hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-β-D-arabinofuranosyl]-9H-purin-6-amine; Clofarabine Triphosphate

Database IDs

• CAS Number: 134646-41-6
• PubChem SID: 162258998
• PubChem CID: 9915350

CALCULATED PROPERTIES

• Acid pKa: 1.0990582
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -7.9352593
• LogD (pH = 7.4): -8.668757
• Log P: -1.7674532
• Molar Refractivity: 99.6208 cm^3
• Polarizability: 39.974777 Å^3
• Polar Surface Area: 258.9 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C586900

A metabolite of Clofarabine (C586890).

REFERENCES

• Parker, W., et al.: Cancer Res., 51, 2386 (1991)
• Huq, F., et al.: J. Pharmacol. Toxicol., 1, 328 (1991)