(1S,10R,11S,14S,15S)-15-methyl-5,14-bis(oxan-2-yloxy)tetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-8-ol

• ChemBase ID: 162230
• Molecular Formular: C28H40O5
• Molecular Mass: 456.6142
• Monoisotopic Mass: 456.28757438
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2O)[C@H]2[C@](CC1)([C@H](CC2)OC1CCCCO1)C)OC1OCCCC1
• Canonical SMILES: OC1C[C@@H]2[C@@H](c3c1cc(cc3)OC1CCCCO1)CC[C@]1([C@H]2CC[C@@H]1OC1CCCCO1)C
• InChI: InChI=1S/C28H40O5/c1-28-13-12-20-19-9-8-18(32-26-6-2-4-14-30-26)16-22(19)24(29)17-21(20)23(28)10-11-25(28)33-27-7-3-5-15-31-27/h8-9,16,20-21,23-27,29H,2-7,10-15,17H2,1H3/t20-,21-,23+,24?,25+,26?,27?,28+/m1/s1
• InChIKey: MCLZNKNXAOPACD-PTTVHZSDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14S,15S)-15-methyl-5,14-bis(oxan-2-yloxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-8-ol
• IUPAC Traditional name: (1S,10R,11S,14S,15S)-15-methyl-5,14-bis(oxan-2-yloxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-8-ol
• Synonyms: (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-ol

Database IDs

• CAS Number: 122566-22-7
• PubChem SID: 162256365
• PubChem CID: 68727916

CALCULATED PROPERTIES

• Acid pKa: 14.391958
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.104845
• LogD (pH = 7.4): 5.104845
• Log P: 5.104845
• Molar Refractivity: 126.7207 cm^3
• Polarizability: 50.486656 Å^3
• Polar Surface Area: 57.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Yellow Powder

DETAILS

Toronto Research Chemicals - B416155

17β-Estradiol (E888000) derivative. Used in the preparation of Δ6-estrogens.

REFERENCES

• Rao, P. & Wang, Z.; Steroids 62, 487 (1997)