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

• ChemBase ID: 131221
• Molecular Formular: C18H22O3
• Molecular Mass: 286.36548
• Monoisotopic Mass: 286.15689456
• SMILES: C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1C[C@H](C2=O)O)O
• Canonical SMILES: Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@H](C2=O)O)C
• 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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
• InChIKey: WPOCIZJTELRQMF-QFXBJFAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one
• IUPAC Traditional name: 16α-hydroxyestrone
• Synonyms: 1,3,5(10)-Estratriene-3,16α-diol-17-one; 16α-Hydroxyestrone; (16α)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one; 3,16α-Dihydroxy-1,3,5(10)-estratrien-17-one; Estra-1,3,5(10)-triene-3,16α-diol-17-one; 16α-Hydroxy Estrone

Database IDs

• CAS Number: 566-76-7
• MDL Number: MFCD00870436
• PubChem SID: 24895817; 162225499
• PubChem CID: 115116

CALCULATED PROPERTIES

• Acid pKa: 10.326568
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.4379566
• LogD (pH = 7.4): 3.4374518
• Log P: 3.437963
• Molar Refractivity: 80.5746 cm^3
• Polarizability: 31.379839 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Pale Pink Solid
• Melting Point: 209-211°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: KG7749550
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281

Product Information

• Purity: ~95% (TLC)

DETAILS

Toronto Research Chemicals - H941900

A major metabolite of Estradiol.

REFERENCES

• Fishman, H.G, et al.: Biochemistry, 8, 4304 (1969)
• Ryan, Sugar, J., et al.: J. Clin. Endocrinol. Metab., 50, 137 (1969)
• Numazawa, M., et al.: Steroids, 38, 149 (1969)
• Travis, R., et al.: Breast Cancer Res., 5, 239 (1969)