(2R,3R,5R)-2-[6-amino-2-fluoro(4,5-13C2,7-15N)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 169028
• Molecular Formular: C10H12FN5O4
• Molecular Mass: 288.21050177
• Monoisotopic Mass: 288.09107668
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1[13c]2[13c]([15n]c1)c(nc(n2)F)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1c[15n][13c]2[13c]1nc(F)nc2N
• InChI: InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5?,6-,9-/m1/s1/i4+1,8+1,13+1
• InChIKey: HBUBKKRHXORPQB-RTXNDTQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-2-[6-amino-2-fluoro(4,5-^1^3C₂,7-^1^5N)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,5R)-2-[6-amino-2-fluoro(4,5-^1^3C₂,7-^1^5N)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 9-β-D-Arabinofuranosyl-2-fluoro-9H-purin-6-amine-13C2,15N; 2-Fluoro-9-β-D-arabinofuranosyladenine-13C2,15N; 2-Fluoroadenine Arabinoside-13C2,15N; NSC 118218-13C2,15N; NSC 118218H-13C2,15N; Fludarabine-13C2,15N

Database IDs

• PubChem SID: 162263160
• PubChem CID: 71316780

CALCULATED PROPERTIES

• Acid pKa: 12.4539995
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.4700091
• LogD (pH = 7.4): -1.4700067
• Log P: -1.4700028
• Molar Refractivity: 64.0592 cm^3
• Polarizability: 24.368654 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Water
• Apperance: White Solid
• Melting Point: 265-268°C

DETAILS

Toronto Research Chemicals - F425002

Used as an antineoplastic.

REFERENCES

• Brockman, R.W., et al.: Biochem. Pharmacol., 26, 2193 (1977)
• Brockman, R.W., et al.: Cancer Res., 40, 3610 (1977)
• Chun, H.G., et al.: Cancer Treat. Rep., 70, 1225 (1977)
• Warrell, R.P., et al.: J. Clin. Oncol., 4, 74 (1977)