(11S,14S,15S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-1(10),2,4,6,8-pentaene-5,14-diol

• ChemBase ID: 167579
• Molecular Formular: C18H20O2
• Molecular Mass: 268.3502
• Monoisotopic Mass: 268.14632988
• SMILES: c1c(cc2c(c1)c1c(cc2)[C@H]2[C@](CC1)([C@H](CC2)O)C)O
• Canonical SMILES: Oc1ccc2c(c1)ccc1c2CC[C@]2([C@H]1CC[C@@H]2O)C
• InChI: InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16-17,19-20H,6-9H2,1H3/t16-,17-,18-/m0/s1
• InChIKey: RYWZPRVUQHMJFF-BZSNNMDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(10),2,4,6,8-pentaene-5,14-diol
• IUPAC Traditional name: (11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(10),2,4,6,8-pentaene-5,14-diol
• Synonyms: (17β)-Estra-1,3,5,7,9-pentaene-3,17-diol; Estra-1,3,5,7,9-pentaene-3,17β-diol; E 380; β-Dihydroequilenin; 17β-Equilenol; 17β-Dihydro Equilenin

Database IDs

• CAS Number: 1423-97-8
• PubChem SID: 162261712
• PubChem CID: 3032407

CALCULATED PROPERTIES

• Acid pKa: 9.785378
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.735506
• LogD (pH = 7.4): 3.7337546
• Log P: 3.7355285
• Molar Refractivity: 79.8579 cm^3
• Polarizability: 32.212566 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D448960

The 17β-metabolite of Equilin (E592800).

REFERENCES

• Enmark, E., et al.: J. Clin. Endocrinol. Metab., 82, 4258 (1997)
• Wang, Z., et al.: J. Med. Chem., 43, 2419 (1997)
• Jiang, X., et al.: Steroids, 71, 334 (1997)