(1S,10R,11S,14R,15S)-5-methoxy-15-methyl-8-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-14-yl acetate

• ChemBase ID: 159370
• Molecular Formular: C21H26O4
• Molecular Mass: 342.42874
• Monoisotopic Mass: 342.18310931
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](CC2=O)[C@H]2[C@](CC1)([C@@H](CC2)OC(=O)C)C)OC
• Canonical SMILES: COc1ccc2c(c1)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@H]2OC(=O)C)C
• InChI: InChI=1S/C21H26O4/c1-12(22)25-20-7-6-18-16-11-19(23)17-10-13(24-3)4-5-14(17)15(16)8-9-21(18,20)2/h4-5,10,15-16,18,20H,6-9,11H2,1-3H3/t15-,16-,18+,20-,21+/m1/s1
• InChIKey: ZPNICKIKMXJXOR-VSHGRSIOSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 20823-31-8
• PubChem SID: 162253505
• PubChem CID: 71312955

CALCULATED PROPERTIES

• Acid pKa: 16.452696
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.1881454
• LogD (pH = 7.4): 3.1881454
• Log P: 3.1881454
• Molar Refractivity: 94.325 cm^3
• Polarizability: 37.257652 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Light Brown Solid

DETAILS

Toronto Research Chemicals - A186820

Estradiol derivative. Used in the preparation of contraceptive steroids.

REFERENCES

• Kundu, N.: Steroids 22, 327 (1973)