(2R,3R,5R)-5-{1-[2-hydroxy(2H4)ethyl]-6-imino-6,9-dihydro-1H-purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 170542
• Molecular Formular: C12H17N5O4
• Molecular Mass: 295.29448
• Monoisotopic Mass: 295.12805405
• SMILES: n1(cnc2c(c1=N)ncn2[C@H]1C[C@H]([C@H](O1)CO)O)CCO
• Canonical SMILES: OCCn1cnc2c(c1=N)ncn2[C@@H]1O[C@@H]([C@@H](C1)O)CO
• InChI: InChI=1S/C12H17N5O4/c13-11-10-12(15-5-16(11)1-2-18)17(6-14-10)9-3-7(20)8(4-19)21-9/h5-9,13,18-20H,1-4H2/t7-,8-,9-/m1/s1
• InChIKey: CFZWOQIYPJCTQP-IWSPIJDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-5-{1-[2-hydroxy(^2H₄)ethyl]-6-imino-6,9-dihydro-1H-purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,3R,5R)-5-{1-[2-hydroxy(^2H₄)ethyl]-6-iminopurin-9-yl}-2-(hydroxymethyl)oxolan-3-ol
• Synonyms: 2'-Deoxy-1-(2-hydroxyethyl-d4)adenosine; 1-Hydroxy(ethyl-d4)-2'-deoxyadenosine

Database IDs

• PubChem SID: 164226452
• PubChem CID: 71749024

CALCULATED PROPERTIES

• Acid pKa: 13.877633
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.8861903
• LogD (pH = 7.4): -1.8823142
• Log P: -1.8822644
• Molar Refractivity: 83.8801 cm^3
• Polarizability: 27.558802 Å^3
• Polar Surface Area: 127.19 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Semi Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H941992

A labelled DNA adduct in relation to in vitro reaction of ethylene oxide with DNA.

REFERENCES

• Li, F., et al.: Chemico-Biological Interactions , 83, 35 (1992)