(1S,10R,11S,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-13-one

• ChemBase ID: 172065
• Molecular Formular: C18H22O3
• Molecular Mass: 286.36548
• Monoisotopic Mass: 286.15689456
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](C(=O)C2)O)C)O
• Canonical SMILES: O=C1C[C@@H]2[C@]([C@H]1O)(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)O
• InChI: InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-15,17,19,21H,2,4,6-7,9H2,1H3/t13-,14-,15+,17+,18+/m1/s1
• InChIKey: KJDGFQJCHFJTRH-YONAWACDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-13-one
• IUPAC Traditional name: 16-ketoestradiol
• Synonyms: (17β)-3,17-Dihydroxyestra-1,3,5(10)-trien-16-one; 1,3,5(10)-Estratriene-3,17β-diol-16-one; 16-Ketoestradiol; 16-Oxo-17β-estradiol; 16-Oxoestradiol; 16-Oxoestradiol-17β; NSC 51169; 16-Keto 17β-Estradiol

Database IDs

• CAS Number: 566-75-6
• PubChem SID: 164227975
• PubChem CID: 66417

CALCULATED PROPERTIES

• Acid pKa: 10.326006
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.0819297
• LogD (pH = 7.4): 3.0814245
• Log P: 3.0819361
• Molar Refractivity: 80.3688 cm^3
• Polarizability: 31.379839 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K188750

A metabolite of Estradiol (E888000).

REFERENCES

• Ball, P., et al.: Steroids, 33, 563 (1979)
• Wong, T., et al.: Clin. Chem., 38, 1830 (1979)
• Xu, X., et al.: J. Clin. Endocrinol. Metab., 84, 3914 (1979)
• Todorovic, R., et al.: Carcinogenesis, 22, 905 (1979)
• Travis, R., et al.: Breast Cancer Res., 5, 23