2-amino-9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,7,8,9-tetrahydro-3H-purine-6,8-dione

• ChemBase ID: 132904
• Molecular Formular: C10H13N5O5
• Molecular Mass: 283.24072
• Monoisotopic Mass: 283.09166854
• SMILES: C1C(C(OC1n1c2c(c(=O)nc([nH]2)N)[nH]c1=O)CO)O
• Canonical SMILES: OCC1OC(CC1O)n1c(=O)[nH]c2c1[nH]c(N)nc2=O
• InChI: InChI=1S/C10H13N5O5/c11-9-13-7-6(8(18)14-9)12-10(19)15(7)5-1-3(17)4(2-16)20-5/h3-5,16-17H,1-2H2,(H,12,19)(H3,11,13,14,18)
• InChIKey: HCAJQHYUCKICQH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,7,8,9-tetrahydro-3H-purine-6,8-dione
• IUPAC Traditional name: 2-amino-9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,7-dihydropurine-6,8-dione
• Synonyms: 8-Oxo-7,8-dihydro-2′-deoxyguanosine; 8-Oxo-dG; 8-Hydroxy-2′-deoxyguanosine

Database IDs

• CAS Number: 88847-89-6
• MDL Number: MFCD00210311
• PubChem SID: 24895702; 162227181
• PubChem CID: 3964517

CALCULATED PROPERTIES

• Acid pKa: 7.5100923
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.4785967
• LogD (pH = 7.4): -2.7294009
• Log P: -2.4746811
• Molar Refractivity: 72.6934 cm^3
• Polarizability: 24.41522 Å^3
• Polar Surface Area: 149.51 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - H5653

Biochem/physiol Actions
A marker compound typically indicative of DNA damage associated with mutagenesis and carcinogenesis