(2R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 164592
• Molecular Formular: C10H12ClN5O3
• Molecular Mass: 285.68698
• Monoisotopic Mass: 285.06286695
• SMILES: C1C([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)Cl)N)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1cnc2c1nc(Cl)nc2N
• InChI: InChI=1S/C10H12ClN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4?,5-,6-/m1/s1
• InChIKey: PTOAARAWEBMLNO-YSLANXFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,5R)-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• Synonyms: 2-Chloro-2’-deoxyadenosine; 2-CdA; NSC-105014-F; Leustatin; Cladribine

Database IDs

• CAS Number: 4291-63-8
• PubChem SID: 162258727
• PubChem CID: 21147181

CALCULATED PROPERTIES

• Acid pKa: 13.886716
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.2817818
• LogD (pH = 7.4): -0.28177568
• Log P: -0.28177547
• Molar Refractivity: 67.1835 cm^3
• Polarizability: 25.93346 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: >220°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C557500

It is a substituted purine nucleoside with antileukemic activity.

REFERENCES

• Seto, S., et al.: J. Clin. Invest., 75, 377 (1985)
• Piro, L.D., et al.: N. Engl. J. Med., 322, 1117 (1985)