(2R,3R,5R)-5-{6-[(2-hydroxyethyl)amino]-9H-purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 170539
• Molecular Formular: C12H17N5O4
• Molecular Mass: 295.29448
• Monoisotopic Mass: 295.12805405
• SMILES: n1cnc2c(c1NCCO)ncn2[C@H]1C[C@H]([C@H](O1)CO)O
• Canonical SMILES: OCCNc1ncnc2c1ncn2[C@@H]1O[C@@H]([C@@H](C1)O)CO
• InChI: InChI=1S/C12H17N5O4/c18-2-1-13-11-10-12(15-5-14-11)17(6-16-10)9-3-7(20)8(4-19)21-9/h5-9,18-20H,1-4H2,(H,13,14,15)/t7-,8-,9-/m1/s1
• InChIKey: KIAMDXBTZWMIAM-IWSPIJDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-5-{6-[(2-hydroxyethyl)amino]-9H-purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,3R,5R)-5-{6-[(2-hydroxyethyl)amino]purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol
• Synonyms: 2'-Deoxy-N-(2-hydroxyethyl)adenosine; N6-(2-Hydroxyethyl)-2'-deoxyadenosine

Database IDs

• CAS Number: 137058-94-7
• PubChem SID: 164226449
• PubChem CID: 71749021

CALCULATED PROPERTIES

• Acid pKa: 13.8767395
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.6690253
• LogD (pH = 7.4): -1.5799887
• Log P: -1.5787238
• Molar Refractivity: 73.4706 cm^3
• Polarizability: 28.184952 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 128-130°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - H941985

A purine deoxynucleoside DNA adduct.

REFERENCES

• Kasai, H., et al.: Carcinogenesis, 19, 1459 (1998)
• Kuchenmeister, F., et al.: Mutat. Res., 419, 69 (1998)
• Kowalczyk, A., et al.: Biochemistry, 41, 3109 (1998)