(1'R,5'S,9'S,10'S,13'R)-5'-methyl-18'-oxaspiro[1,3-dioxolane-2,15'-pentacyclo[11.4.1.01,13.02,10.05,9]octadecan]-2'-en-6'-one

• ChemBase ID: 168115
• Molecular Formular: C20H26O4
• Molecular Mass: 330.41804
• Monoisotopic Mass: 330.18310931
• SMILES: C1CC2(C[C@@]34[C@@]1(C1=CC[C@]5([C@H]([C@@H]1CC3)CCC5=O)C)O4)OCCO2
• Canonical SMILES: O=C1CC[C@@H]2[C@]1(C)CC=C1[C@H]2CC[C@@]23[C@]1(CCC1(C3)OCCO1)O2
• InChI: InChI=1S/C20H26O4/c1-17-6-5-15-13(14(17)2-3-16(17)21)4-7-18-12-19(22-10-11-23-19)8-9-20(15,18)24-18/h5,13-14H,2-4,6-12H2,1H3/t13-,14-,17-,18+,20+/m0/s1
• InChIKey: BAMMJXIMVWLRCU-YAUBAPCASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,5'S,9'S,10'S,13'R)-5'-methyl-18'-oxaspiro[1,3-dioxolane-2,15'-pentacyclo[11.4.1.0^1,^1^3.0^2,^1^0.0^5,^9]octadecan]-2'-en-6'-one
• IUPAC Traditional name: (1'R,5'S,9'S,10'S,13'R)-5'-methyl-18'-oxaspiro[1,3-dioxolane-2,15'-pentacyclo[11.4.1.0^1,^1^3.0^2,^1^0.0^5,^9]octadecan]-2'-en-6'-one
• Synonyms: (5α,10α)-5,10-Epoxy-estr-9(11)-ene-3,17-dione Cyclic 3-(1,2-Ethanediyl Acetal)

Database IDs

• CAS Number: 39931-87-8
• PubChem SID: 162262247
• PubChem CID: 10735192

CALCULATED PROPERTIES

• Acid pKa: 19.862255
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.8945613
• LogD (pH = 7.4): 2.8945613
• Log P: 2.8945613
• Molar Refractivity: 88.2298 cm^3
• Polarizability: 35.11863 Å^3
• Polar Surface Area: 48.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Pale Yellow Solid
• Melting Point: 135-139°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E589205

Intermediate in the preparation of Mifepristone metabolites.

REFERENCES

• Nique, F., et al.: J. Steroid Biochem., Mol. Biol., 50, 21 (1994)
• Jiang, W., et al.: Steroids, 71, 949 (1994)
• Jin, C., et al.: Bioorg. Med. Chem. Lett., 17, 5754 (1994)