2-amino-7-[(1S,10R,11S,14S,15S)-5,6,14-trihydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-3-yl]-6,7-dihydro-1H-purin-6-one

• ChemBase ID: 170558
• Molecular Formular: C23H27N5O4
• Molecular Mass: 437.49158
• Monoisotopic Mass: 437.20630437
• SMILES: c1c(c(c2c(c1n1c3c(nc1)nc([nH]c3=O)N)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)O)C)O)O
• Canonical SMILES: Nc1nc2ncn(c2c(=O)[nH]1)c1cc(O)c(c2c1[C@H]1CC[C@]3([C@H]([C@@H]1CC2)CC[C@@H]3O)C)O
• InChI: InChI=1S/C23H27N5O4/c1-23-7-6-11-10(13(23)4-5-16(23)30)2-3-12-17(11)14(8-15(29)19(12)31)28-9-25-20-18(28)21(32)27-22(24)26-20/h8-11,13,16,29-31H,2-7H2,1H3,(H3,24,26,27,32)/t10-,11+,13+,16+,23+/m1/s1
• InChIKey: FRKBGPSXUBCIFE-URRUNNDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-7-[(1S,10R,11S,14S,15S)-5,6,14-trihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-3-yl]-6,7-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-7-[(1S,10R,11S,14S,15S)-5,6,14-trihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-3-yl]-1H-purin-6-one
• Synonyms: 2-Amino-1,7-dihydro-7-[(17β)-3,4,17-trihydroxyestra-1,3,5(10)-trien-1-yl]-6H-purin-6-one; 4-OH-E2-1-N7Gua; 4-Hydroxy Estradiol 1-N7-Guanine

Database IDs

• CAS Number: 178971-91-0
• PubChem SID: 164226468
• PubChem CID: 71749036

CALCULATED PROPERTIES

• Acid pKa: 9.877169
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 1.4464793
• LogD (pH = 7.4): 1.4450749
• Log P: 1.4465
• Molar Refractivity: 130.1557 cm^3
• Polarizability: 44.849167 Å^3
• Polar Surface Area: 145.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942115

4-Hydroxy Estradiol 1-N7-Guanine is an estrogen metabolite formed with DNA which can lead to the mutations that initiate breast, prostate, and other types of cancer. Estrogen-DNA depurinating adducts as biomarkers of cancer risk and their use in cancer de

REFERENCES

• Chakravarti, D., et al.: Mutat. Res., 456, 17 (2000)
• Liehr, J., et al.: Endocr. Rev., 21, 4054 (2000)
• Chakravarti, D., et al.: Oncogene, 20, 7945 (2000)
• Cavalieri, E., et al.: Chem. Res. Toxicol., 14, 1041 (2000)