2-amino-7-(2-hydroxyethyl)-6,7-dihydro-1H-purin-6-one

• ChemBase ID: 170571
• Molecular Formular: C7H9N5O2
• Molecular Mass: 195.17866
• Monoisotopic Mass: 195.07562455
• SMILES: [nH]1c(nc2c(c1=O)n(cn2)CCO)N
• Canonical SMILES: OCCn1cnc2c1c(=O)[nH]c(n2)N
• InChI: InChI=1S/C7H9N5O2/c8-7-10-5-4(6(14)11-7)12(1-2-13)3-9-5/h3,13H,1-2H2,(H3,8,10,11,14)
• InChIKey: OCAWYYAMQRJCOY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-7-(2-hydroxyethyl)-6,7-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-7-(2-hydroxyethyl)-1H-purin-6-one
• Synonyms: 2-Amino-1,7-dihydro-7-(2-hydroxyethyl)-6H-purin-6-one; 7-(2-Hydroxyethyl)guanine; 7-(β-Hydroxyethyl)guanine; NSC 637506; N7-(2-Hydroxyethyl)guanine

Database IDs

• CAS Number: 53498-52-5
• PubChem SID: 164226481
• PubChem CID: 105076

CALCULATED PROPERTIES

• Acid pKa: 10.718137
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.5735129
• LogD (pH = 7.4): -1.5735601
• Log P: -1.5733757
• Molar Refractivity: 50.5235 cm^3
• Polarizability: 17.345917 Å^3
• Polar Surface Area: 105.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow Solid
• Melting Point: >300°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H942200

An ethylene oxide-DNA adduct. Ethylene oxide (EtO) is classified as a known human carcinogen. The formation of EtO-DNA adducts is considered as an important early event in the EtO carcinogenic process.

REFERENCES

• Walker, V., et al.: Cancer Res., 52, 4320 (1992)
• Wu, K., et al.: Chem. Res. Toxicol., 12, 722 (1992)
• van Sittert, N., et al.: Mutat. Res., 447, 27 (1992)