(1S,8R,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-5,8,14-triol

• ChemBase ID: 170501
• Molecular Formular: C18H24O3
• Molecular Mass: 288.38136
• Monoisotopic Mass: 288.17254463
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](C[C@H]2O)[C@H]2[C@](CC1)([C@H](CC2)O)C)O
• Canonical SMILES: Oc1ccc2c(c1)[C@H](O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
• InChI: InChI=1S/C18H24O3/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+,16-,17+,18+/m1/s1
• InChIKey: QZZRQURPSRWTLG-UXCAXZQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,8R,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,8,14-triol
• IUPAC Traditional name: 6β-hydroxy-17β-estradiol
• Synonyms: (6β,17β)-Estra-1,3,5(10)-triene-3,6,17-triol; Estra-1,3,5(10)-triene-3,6β,17β-triol; 6β-Hydroxyestradiol; E 2550; 6β-Hydroxy 17β-Estradiol

Database IDs

• CAS Number: 3583-03-7
• PubChem SID: 164226411
• PubChem CID: 440168

CALCULATED PROPERTIES

• Acid pKa: 9.622359
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.5146575
• LogD (pH = 7.4): 2.5121102
• Log P: 2.5146902
• Molar Refractivity: 81.4202 cm^3
• Polarizability: 31.996971 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941850

A metabolite of Estradiol (E888000).

REFERENCES

• Greene, G., et al.: Science, 231, 1150 (1986)
• Cushman, M., et al.: J. Med. Chem., 38, 2041 (1986)
• Zhu, B., et al.: Steroids, 70, 225 (1986)