(1S,10R,11S,14S,15S)-3-(6-amino-3H-purin-3-yl)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-triene-5,6,14-triol

• ChemBase ID: 170557
• Molecular Formular: C23H27N5O3
• Molecular Mass: 421.49218
• Monoisotopic Mass: 421.21138975
• SMILES: c1c(c(c2c(c1n1cnc(c3c1ncn3)N)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)O)C)O)O
• Canonical SMILES: O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1c(cc(c2O)O)n1cnc(c2c1ncn2)N
• InChI: InChI=1S/C23H27N5O3/c1-23-7-6-12-11(14(23)4-5-17(23)30)2-3-13-18(12)15(8-16(29)20(13)31)28-10-27-21(24)19-22(28)26-9-25-19/h8-12,14,17,29-31H,2-7,24H2,1H3/t11-,12+,14+,17+,23+/m1/s1
• InChIKey: LWOXXVDIEGNZNP-GXPADDFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14S,15S)-3-(6-amino-3H-purin-3-yl)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,6,14-triol
• IUPAC Traditional name: (1S,10R,11S,14S,15S)-3-(6-aminopurin-3-yl)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,6,14-triol
• Synonyms: (17β)-1-(6-Amino-3H-purin-3-yl)estra-1,3,5(10)-triene-3,4,17-triol; 4-OH-E2-1-N3Ade; 4-Hydroxy Estradiol 1-N3-Adenine

Database IDs

• CAS Number: 428506-88-1
• PubChem SID: 164226467
• PubChem CID: 71749035

CALCULATED PROPERTIES

• Acid pKa: 9.963741
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 2.3428645
• LogD (pH = 7.4): 2.3424098
• Log P: 2.3436
• Molar Refractivity: 127.4205 cm^3
• Polarizability: 45.188942 Å^3
• Polar Surface Area: 130.31 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942100

4-Hydroxy Estradiol 1-N3-Adenine is an estrogen metabolite formed with DNA which can lead to the mutations that initiate breast, prostate, and other types of cancer. The N3Ade depurinating adducts could serve as biomarkers to predict the risk of breast ca

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)