(1S,10R,11S,14S,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-8-one

• ChemBase ID: 133377
• Molecular Formular: C18H22O3
• Molecular Mass: 286.36548
• Monoisotopic Mass: 286.15689456
• SMILES: C[C@]12CC[C@@H]3c4ccc(cc4C(=O)C[C@H]3[C@@H]1CC[C@@H]2O)O
• Canonical SMILES: Oc1ccc2c(c1)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
• InChI: InChI=1S/C18H22O3/c1-18-7-6-12-11-3-2-10(19)8-14(11)16(20)9-13(12)15(18)4-5-17(18)21/h2-3,8,12-13,15,17,19,21H,4-7,9H2,1H3/t12-,13-,15+,17+,18+/m1/s1
• InChIKey: ZHTDDOWJIRXOMA-YVEZLPLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14S,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-8-one
• IUPAC Traditional name: (1S,10R,11S,14S,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-8-one
• Synonyms: 1,3,5-Estratriene-3,17β-diol-6-one; 3,17β-Dihydroxy-1,3,5(10)-estratrien-6-one; 6-Ketoestradiol; β-Estradiol-6-one; (17β)-3,17-Dihydroxyestra-1,3,5(10)-trien-6-one; 3,17β-Dihydroxyestra-1,3,5(10)-trien-6-one; 1,3,5(10)-Estratrien-3,17β-diol-6-one; 6-Oxo-17β-estradiol; 6-Oxoestradiol; 6-Keto-17β-Estradiol; NSC 147966; 6-Keto 17β-Estradiol

Database IDs

• CAS Number: 571-92-6
• MDL Number: MFCD00056457
• Beilstein Number: 3208779
• PubChem SID: 162227654
• PubChem CID: 66419

CALCULATED PROPERTIES

• Acid pKa: 8.882315
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.600947
• LogD (pH = 7.4): 2.5871437
• Log P: 2.601126
• Molar Refractivity: 80.6912 cm^3
• Polarizability: 31.511963 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform/methanol (9:1): soluble10 mg/mL, clear, colorless
• Melting Point: 281-283 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C18H22O3

DETAILS

Toronto Research Chemicals - K188740

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