(1'S,2'R,7'R,9'S,11'S,12'S,15'R,16'S)-2',16'-dimethyl-15'-(2-methyl-1,3-dioxolan-2-yl)-8'-oxaspiro[1,3-dioxolane-2,5'-pentacyclo[9.7.0.02,7.07,9.012,16]octadecane]-15'-ol

• ChemBase ID: 168114
• Molecular Formular: C25H38O6
• Molecular Mass: 434.56562
• Monoisotopic Mass: 434.26683894
• SMILES: [C@@]12([C@@]3([C@H](C[C@@H]4[C@@H]1CC[C@]1([C@H]4CC[C@@]1(C1(C)OCCO1)O)C)O3)CC1(CC2)OCCO1)C
• Canonical SMILES: C[C@@]12CCC3(C[C@]42O[C@H]4C[C@@H]2[C@@H]1CC[C@]1([C@H]2CC[C@]1(O)C1(C)OCCO1)C)OCCO3
• InChI: InChI=1S/C25H38O6/c1-20-8-9-23(29-12-13-30-23)15-24(20)19(31-24)14-16-17(20)4-6-21(2)18(16)5-7-25(21,26)22(3)27-10-11-28-22/h16-19,26H,4-15H2,1-3H3/t16-,17+,18+,19+,20-,21+,24+,25-/m1/s1
• InChIKey: DJFFGYOVKDHICP-VCACCMGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2'R,7'R,9'S,11'S,12'S,15'R,16'S)-2',16'-dimethyl-15'-(2-methyl-1,3-dioxolan-2-yl)-8'-oxaspiro[1,3-dioxolane-2,5'-pentacyclo[9.7.0.0^2,^7.0^7,^9.0^1^2,^1^6]octadecane]-15'-ol
• IUPAC Traditional name: (1'S,2'R,7'R,9'S,11'S,12'S,15'R,16'S)-2',16'-dimethyl-15'-(2-methyl-1,3-dioxolan-2-yl)-8'-oxaspiro[1,3-dioxolane-2,5'-pentacyclo[9.7.0.0^2,^7.0^7,^9.0^1^2,^1^6]octadecane]-15'-ol
• Synonyms: (5α,6α)-5,6-Epoxy-17-hydroxy-pregnane-3,20-dione Cyclic Bis(1,2-ethanediyl Acetal); (5α,6α)-Epoxy-17α-hydroxy-pregnane-3,20-dione-3,20-bis(ethyleneketal)

Database IDs

• CAS Number: 3496-78-4
• PubChem SID: 162262246
• PubChem CID: 71316375

CALCULATED PROPERTIES

• Acid pKa: 12.648898
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.1973825
• LogD (pH = 7.4): 3.19738
• Log P: 3.1973825
• Molar Refractivity: 112.4316 cm^3
• Polarizability: 45.798786 Å^3
• Polar Surface Area: 69.68 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - E589201

A byproduct formed during Medroxyprogesteron synthesis.

REFERENCES

• Takeda, K., et al.: Chem. Pharm. Bull., 12, 1433 (1964)