2-amino-9-[3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one

• ChemBase ID: 133146
• Molecular Formular: C10H13N5O4
• Molecular Mass: 267.24132
• Monoisotopic Mass: 267.09675392
• SMILES: c1nc2c(n1C1C(CC(O1)CO)O)[nH]c(nc2=O)N
• Canonical SMILES: Nc1nc(=O)c2c([nH]1)n(C1OC(CC1O)CO)cn2
• InChI: InChI=1S/C10H13N5O4/c11-10-13-7-6(8(18)14-10)12-3-15(7)9-5(17)1-4(2-16)19-9/h3-5,9,16-17H,1-2H2,(H3,11,13,14,18)
• InChIKey: OROIAVZITJBGSM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
• Synonyms: 3′-Deoxyguanosine

Database IDs

• CAS Number: 3608-58-0
• MDL Number: MFCD00079149
• PubChem SID: 24894100; 162227423
• PubChem CID: 4238386

CALCULATED PROPERTIES

• Acid pKa: 7.9819307
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.5003136
• LogD (pH = 7.4): -1.5938604
• Log P: -1.4983127
• Molar Refractivity: 63.0906 cm^3
• Polarizability: 23.80684 Å^3
• Polar Surface Area: 134.99 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

DETAILS

Sigma Aldrich - D7285

Application
3′-Deoxyguanosine (3dG) is used as a complexing ligand for enzymes, such as purine nucleoside phosphorylase (PNP), and receptors, such as G-coupled receptors, to enable structure analysis. 3′-Deoxyguanosine may be used to selectively impair transcription but not polyadenylation.