2-amino-9-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-{[4-(2H5)phenylphenyl]amino}-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 165971
• Molecular Formular: C22H22N6O4
• Molecular Mass: 434.44788
• Monoisotopic Mass: 434.17025321
• SMILES: C1C([C@H](O[C@H]1n1c2c(nc1Nc1ccc(cc1)c1ccccc1)c(=O)[nH]c(n2)N)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1c(Nc2ccc(cc2)c2ccccc2)nc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C22H22N6O4/c23-21-26-19-18(20(31)27-21)25-22(28(19)17-10-15(30)16(11-29)32-17)24-14-8-6-13(7-9-14)12-4-2-1-3-5-12/h1-9,15-17,29-30H,10-11H2,(H,24,25)(H3,23,26,27,31)/t15?,16-,17-/m1/s1
• InChIKey: JPQHAFBEGLGQRF-YJEKIOLLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-{[4-(^2H₅)phenylphenyl]amino}-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-{[4-(^2H₅)phenylphenyl]amino}-1H-purin-6-one
• Synonyms: 8-([1,1'-Biphenyl]-4-ylamino)-2'-deoxy-guanosine-d5; DG-C8-ABP-d5; N-(2'-Deoxyguanosin-8-yl)-4-amino(biphenyl-2',3',4',5'-d5)

Database IDs

• PubChem SID: 162260104
• PubChem CID: 71315484

CALCULATED PROPERTIES

• Acid pKa: 10.160952
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 1.9658014
• LogD (pH = 7.4): 1.9651544
• Log P: 1.965821
• Molar Refractivity: 116.2061 cm^3
• Polarizability: 45.063023 Å^3
• Polar Surface Area: 147.02 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Brown Solid
• Melting Point: >255°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D239602

The deuterated DNA adduct of 4-Aminobiphenyl.

REFERENCES

• Beland, F.A., et al.: Chem. Res. Toxicol., 12, 68 (1999)