(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-5-yl pentanoate

• ChemBase ID: 168278
• Molecular Formular: C23H30O3
• Molecular Mass: 354.4825
• Monoisotopic Mass: 354.21949482
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)OC(=O)CCCC
• Canonical SMILES: CCCCC(=O)Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C
• InChI: InChI=1S/C23H30O3/c1-3-4-5-22(25)26-16-7-9-17-15(14-16)6-8-19-18(17)12-13-23(2)20(19)10-11-21(23)24/h7,9,14,18-20H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,23+/m1/s1
• InChIKey: FQLHSYGNONSVOX-UGTOYMOASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl pentanoate
• IUPAC Traditional name: (1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl pentanoate
• Synonyms: 3-[(1-Oxopentyl)oxy]estra-1,3,5(10)-trien-17-one; Estrone 3-Valerate

Database IDs

• CAS Number: 128788-26-1
• PubChem SID: 162262410
• PubChem CID: 71316495

CALCULATED PROPERTIES

• Acid pKa: 19.957535
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.8095284
• LogD (pH = 7.4): 5.8095284
• Log P: 5.8095284
• Molar Refractivity: 102.0628 cm^3
• Polarizability: 40.10682 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E889100

An Estrone (E889050) mesogen, an ester of Estrone with valeric acid. Several derivative of Estrone are found to have a cholesteric mesophase.

REFERENCES

• Miescher, K., et al.: Helv. Chimica Acta, 20, 263 (1937)