(1S,10S,11S,14S,15S)-(13,13,14,15-2H4)tetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-5,14-diol

• ChemBase ID: 175608
• Molecular Formular: C17H22O2
• Molecular Mass: 258.35538
• Monoisotopic Mass: 258.16197994
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](CC2)[C@H]2[C@H](CC1)[C@H](CC2)O)O
• Canonical SMILES: O[C@H]1CC[C@@H]2[C@@H]1CC[C@H]1[C@H]2CCc2c1ccc(c2)O
• InChI: InChI=1S/C17H22O2/c18-11-2-4-12-10(9-11)1-3-14-13(12)5-6-16-15(14)7-8-17(16)19/h2,4,9,13-19H,1,3,5-8H2/t13-,14-,15+,16?,17+/m1/s1
• InChIKey: MSBFOZNDVHIKJM-BJCAYOAGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10S,11S,14S,15S)-(13,13,14,15-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,14-diol
• IUPAC Traditional name: (1S,10S,11S,14S,15S)-(13,13,14,15-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,14-diol
• Synonyms: (17β)-Gona-1,3,5(10)-triene-3,17-diol-d4; 18,19-Dinorandrosta-1,3,5(10)-triene-3,17β-diol-d4; Gona-1,3,5(10)-triene-3,17β-diol-d4; 17β,18-Norestradiol-d4; 18-Nor-17β-estradiol-d4

Database IDs

• PubChem SID: 164231518
• PubChem CID: 71751188

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 10.327149
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.3674939
• LogD (pH = 7.4): 3.36699
• Log P: 3.3675005
• Molar Refractivity: 75.5066 cm^3
• Polarizability: 29.466114 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0

DETAILS

Toronto Research Chemicals - N674802

A novel Estradiol (E888000) intermediate as selectively active estrogens. The specificity of the estrogen-receptor in human breast carcinoma was determine by incubating the cytosol fraction with 17β-estradiol-3H alone or in the presence of other steroids.

REFERENCES

• Loke, K., et al.: J. Biochem., 71, 230 (1957)