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

• ChemBase ID: 170559
• Molecular Formular: C23H25N5O4
• Molecular Mass: 435.4757
• Monoisotopic Mass: 435.19065431
• SMILES: c1c(c(c2c(c1n1c3c(nc1)nc([nH]c3=O)N)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)O)O
• Canonical SMILES: Nc1nc2ncn(c2c(=O)[nH]1)c1cc(O)c(c2c1[C@H]1CC[C@]3([C@H]([C@@H]1CC2)CCC3=O)C)O
• InChI: InChI=1S/C23H25N5O4/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/h8-11,13,29,31H,2-7H2,1H3,(H3,24,26,27,32)/t10-,11+,13+,23+/m1/s1
• InChIKey: LBPGOOJJEWNDMR-MQGMTOSNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-7-[(1S,10R,11S,15S)-5,6-dihydroxy-15-methyl-14-oxotetracyclo[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,15S)-5,6-dihydroxy-15-methyl-14-oxotetracyclo[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-7-(3,4-dihydroxy-17-oxoestra-1,3,5(10)-trien-1-yl)-1,7-dihydro-6H-purin-6-one; 4-OH-E1-1-N7Gua; 4-Hydroxy Estrone 1-N7-Guanine

Database IDs

• CAS Number: 178971-92-1
• PubChem SID: 164226469
• PubChem CID: 9889189

CALCULATED PROPERTIES

• Acid pKa: 9.877094
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 2.2738795
• LogD (pH = 7.4): 2.2724745
• Log P: 2.2739
• Molar Refractivity: 129.3334 cm^3
• Polarizability: 44.307335 Å^3
• Polar Surface Area: 142.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942120

4-Hydroxy Estrone 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 dete

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)