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

• ChemBase ID: 168257
• 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)CC)C)O
• Canonical SMILES: CCC(=O)O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)O
• InChI: InChI=1S/C21H28O3/c1-3-20(23)24-19-9-8-18-17-6-4-13-12-14(22)5-7-15(13)16(17)10-11-21(18,19)2/h5,7,12,16-19,22H,3-4,6,8-11H2,1-2H3/t16-,17-,18+,19+,21+/m1/s1
• InChIKey: PQCRZWCSVWBYSC-AGRFSFNASA-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 propanoate
• 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 propanoate
• Synonyms: (17β)-Estra-1,3,5(10)-triene-3,17-diol 17-Propanoate; Estradiol 17-Propionate 17β-Estradiol 17-Propionate; Akrofollin; Estradiol Propionate; Oestra-1,3,5(10)-trien-3,17β-diol 17-Propionate; Estradiol 17-Propionate

Database IDs

• CAS Number: 3758-34-7
• PubChem SID: 162262389
• PubChem CID: 19571

CALCULATED PROPERTIES

• Acid pKa: 10.327061
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.887156
• LogD (pH = 7.4): 4.886652
• Log P: 4.8871627
• Molar Refractivity: 93.6831 cm^3
• Polarizability: 36.976276 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E888815

A 17β-estradiol ester as prodrug of Estradiol (E888000).

REFERENCES

• Kabasakalian, P., et al.: J. Pharm. Sci., 55, 642 (1966)
• Marsh, M., et al.: Br. Med. Bull., 48, 426 (1966)