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

• ChemBase ID: 168247
• Molecular Formular: C22H30O3
• Molecular Mass: 342.4718
• Monoisotopic Mass: 342.21949482
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)OC(=O)CCC)C)O
• Canonical SMILES: CCCC(=O)O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)O
• InChI: InChI=1S/C22H30O3/c1-3-4-21(24)25-20-10-9-19-18-7-5-14-13-15(23)6-8-16(14)17(18)11-12-22(19,20)2/h6,8,13,17-20,23H,3-5,7,9-12H2,1-2H3/t17-,18-,19+,20+,22+/m1/s1
• InChIKey: XRKFWLKYSYKIKT-KOVVAJLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-14-yl butanoate
• IUPAC Traditional name: (1S,10R,11S,14S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-14-yl butanoate
• Synonyms: (17β)-Estra-1,3,5(10)-triene-3,17-diol 17-Butanoate; Estradiol 17-Butyrate

Database IDs

• CAS Number: 18069-79-9
• PubChem SID: 162262379
• PubChem CID: 66845

CALCULATED PROPERTIES

• Acid pKa: 10.327061
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.3317246
• LogD (pH = 7.4): 5.3312206
• Log P: 5.3317313
• Molar Refractivity: 98.2841 cm^3
• Polarizability: 38.818638 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E888040

An Estradiol (E888000) 17-monoester. Short-chain fatty acid esters have a higher binding potency to the estrogen receptor than long-chain fatty acid esters. Estradiol fatty acyl esters act as a storage form from which estradiol is released by enzymic hydr

REFERENCES

• Abul-Hajj, Y.J., et al.: Steroids, 42, 417 (1983)