(3R,4R,5R,7S)-5-[2-amino-6-oxo-6,7-dihydro(2-13C,1-15N)-3H-purin-7-yl]-4-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,9,11,13(17)-tetraene-16,18-dione

• ChemBase ID: 159583
• Molecular Formular: C22H17N5O8
• Molecular Mass: 482.37855263
• Monoisotopic Mass: 482.10513715
• SMILES: [C@H]1(O[C@H]2[C@@H]([C@H]1O)c1c(O2)cc(c2c1oc(=O)c1c2CCC1=O)OC)n1cnc2c1c(=O)[15n][13c]([nH]2)[15NH2]
• Canonical SMILES: COc1cc2O[C@@H]3[C@H](c2c2c1c1CCC(=O)c1c(=O)o2)[C@H]([C@@H](O3)n1cnc2c1c(=O)[15n][13c]([nH]2)[15NH2])O
• InChI: InChI=1S/C22H17N5O8/c1-32-8-4-9-12(16-11(8)6-2-3-7(28)10(6)20(31)34-16)13-15(29)19(35-21(13)33-9)27-5-24-17-14(27)18(30)26-22(23)25-17/h4-5,13,15,19,21,29H,2-3H2,1H3,(H3,23,25,26,30)/t13-,15-,19-,21+/m1/s1/i22+1,23+1,26+1
• InChIKey: XIOUDSNTNJNQQG-VLKYFSKZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,5R,7S)-5-[2-amino-6-oxo-6,7-dihydro(2-^1^3C,1-^1^5N)-3H-purin-7-yl]-4-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^2,^9.0^3,^7.0^1^3,^1^7]nonadeca-1,9,11,13(17)-tetraene-16,18-dione
• IUPAC Traditional name: (3R,4R,5R,7S)-5-[2-amino-6-oxo(2-^1^3C,1-^1^5N)-3H-purin-7-yl]-4-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^2,^9.0^3,^7.0^1^3,^1^7]nonadeca-1,9,11,13(17)-tetraene-16,18-dione
• Synonyms: (6aS,8R,9R,9aR)-8-(2-Amino-1,6-dihydro-6-oxo-7H-purin-7-yl)-2,3,6a,8,9,9a-hexahydro-9-hydroxy-4-methoxy-cyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione-13C,15N2; AFB-Guanine-13C,15N2

Database IDs

• PubChem SID: 162253718
• PubChem CID: 71313051

CALCULATED PROPERTIES

• Acid pKa: 9.206976
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): 0.54708415
• LogD (pH = 7.4): 0.54085356
• Log P: 0.5472677
• Molar Refractivity: 116.0591 cm^3
• Polarizability: 43.618034 Å^3
• Polar Surface Area: 176.59 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A355352

A labelled guanine adduct of Aflatoxin B1.

REFERENCES

• Alvarez, M., et al.: Nat. Tox., 7, 139 (1999)
• Ross, M., et al.: Tox. Sci., 53, 224 (1999)
• Sotomayor, R., et al.: Toxicol. Sci., 73, 329 (1999)