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

• ChemBase ID: 170529
• Molecular Formular: C18H22O3
• Molecular Mass: 286.36548
• Monoisotopic Mass: 286.15689456
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](C[C@@H]2O)[C@H]2[C@](CC1)(C(=O)CC2)C)O
• Canonical SMILES: Oc1ccc2c(c1)[C@@H](O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)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/h2-3,8,12-13,15-16,19-20H,4-7,9H2,1H3/t12-,13-,15+,16+,18+/m1/s1
• InChIKey: HTORTGVWUGQTHQ-WUAUYOTNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,8S,10R,11S,15S)-5,8-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one
• IUPAC Traditional name: (1S,8S,10R,11S,15S)-5,8-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one
• Synonyms: (6α)-3,6-Dihydroxyestra-1,3,5(10)-trien-17-one; 3,6α-Dihydroxyestra-1,3,5(10)-trien-17-one; 6α-Hydroxyestrone; 6α-Hydroxy Estrone

Database IDs

• CAS Number: 1476-78-4
• PubChem SID: 164226439
• PubChem CID: 21122975

CALCULATED PROPERTIES

• Acid pKa: 9.622256
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.0781853
• LogD (pH = 7.4): 3.0756373
• Log P: 3.078218
• Molar Refractivity: 80.5979 cm^3
• Polarizability: 31.450832 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941935

The oxidative 6α-metabolite of 17β-Estradiol (E887995) and Estrone (E889050) formed by 15 selectively expressed human cytochrome p450 isoforms.

REFERENCES

• Grose, K., et al.: Chem. Res. Toxicol., 5, 188 (1992)
• Chang, Y., et al.: Biochem. Pharmacol., 58, 825 (1992)
• Hong, C., et al.: Carcinogenesis, 23, 1297 (1992)