(1S,10R,11S,14S,15S)-14-hydroxy-5-methoxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-8-one

• ChemBase ID: 174253
• Molecular Formular: C19H24O3
• Molecular Mass: 300.39206
• Monoisotopic Mass: 300.17254463
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](CC2=O)[C@H]2[C@](CC1)([C@H](CC2)O)C)OC
• Canonical SMILES: COc1ccc2c(c1)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
• InChI: InChI=1S/C19H24O3/c1-19-8-7-13-12-4-3-11(22-2)9-15(12)17(20)10-14(13)16(19)5-6-18(19)21/h3-4,9,13-14,16,18,21H,5-8,10H2,1-2H3/t13-,14-,16+,18+,19+/m1/s1
• InChIKey: IYIZICLBCDWABT-AFTVQHQSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14S,15S)-14-hydroxy-5-methoxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-8-one
• IUPAC Traditional name: (1S,10R,11S,14S,15S)-14-hydroxy-5-methoxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-8-one
• Synonyms: 17β-Hydroxy-3-methoxy-estra-1,3,5(10)-trien-6-one; 17β-Hydroxy-3-methoxyestra-1,3,5(10)-trien-6-one; 3-O-Methyl-6-oxo 17β-Estradiol

Database IDs

• CAS Number: 50731-96-9
• PubChem SID: 164230163
• PubChem CID: 15542356

CALCULATED PROPERTIES

• Acid pKa: 16.453077
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.74702
• LogD (pH = 7.4): 2.74702
• Log P: 2.74702
• Molar Refractivity: 85.1735 cm^3
• Polarizability: 33.42475 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Pink Solid

DETAILS

Toronto Research Chemicals - M326255

Estradiol derivative. Used in the preparation of contraceptive steroids.

REFERENCES

• Rao, P.: Steroids 23, 173 (1974)
• Kundu, N.: Steroids 22, 327 (1973)