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

• ChemBase ID: 159371
• Molecular Formular: C21H28O3
• Molecular Mass: 328.44522
• Monoisotopic Mass: 328.20384476
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@@H](CC2)OC(=O)C)C)OC
• Canonical SMILES: COc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@H]2OC(=O)C)C
• InChI: InChI=1S/C21H28O3/c1-13(22)24-20-9-8-19-18-6-4-14-12-15(23-3)5-7-16(14)17(18)10-11-21(19,20)2/h5,7,12,17-20H,4,6,8-11H2,1-3H3/t17-,18-,19+,20-,21+/m1/s1
• InChIKey: FMNPCVNWRFPDCA-ADAARDCZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-5-methoxy-15-methyltetracyclo[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-methyltetracyclo[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)-triene; 3-Methoxy-1,3,5(10)-estratrien-17β-ol Acetate; 3-Methoxy-17β-acetoxyestra-1,3,5(10)-triene; Estradiol 17-Acetate 3-Methyl Ether; Estradiol 3-Methyl Ether 17-Acetate; 17-O-Acetyl-3-O-methyl 17β-Estradiol

Database IDs

• CAS Number: 5976-55-6
• PubChem SID: 162253506
• PubChem CID: 11267449

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.332521
• LogD (pH = 7.4): 4.332521
• Log P: 4.332521
• Molar Refractivity: 93.5385 cm^3
• Polarizability: 37.048374 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate

DETAILS

Toronto Research Chemicals - A186830

Estradiol derivative. Used in the preparation of hydroxy steroid dehydrogenese inhibitors.

REFERENCES

• Goldman, A. et al.: Enzymology 315, 233 (1973)