(1'R,2S,2'R,3'S,5'S,7'S,10'S,11'R)-7',11'-dimethylspiro[oxolane-2,6'-pentacyclo[8.8.0.02,7.03,5.011,16]octadecan]-15'-ene-5,14'-dione

• ChemBase ID: 165776
• Molecular Formular: C23H30O3
• Molecular Mass: 354.4825
• Monoisotopic Mass: 354.21949482
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@@]1([C@@H]3[C@H]2C3)CCC(=O)O1)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1[C@@H]1C[C@@H]1[C@]12CCC(=O)O1)C)C
• InChI: InChI=1S/C23H30O3/c1-21-8-5-14(24)11-13(21)3-4-15-17(21)6-9-22(2)20(15)16-12-18(16)23(22)10-7-19(25)26-23/h11,15-18,20H,3-10,12H2,1-2H3/t15-,16-,17+,18+,20-,21+,22+,23+/m1/s1
• InChIKey: DYIJDDWIJGVQBE-PJPXKQQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,2S,2'R,3'S,5'S,7'S,10'S,11'R)-7',11'-dimethylspiro[oxolane-2,6'-pentacyclo[8.8.0.0^2,^7.0^3,^5.0^1^1,^1^6]octadecan]-15'-ene-5,14'-dione
• IUPAC Traditional name: (1'R,2S,2'R,3'S,5'S,7'S,10'S,11'R)-7',11'-dimethylspiro[oxolane-2,6'-pentacyclo[8.8.0.0^2,^7.0^3,^5.0^1^1,^1^6]octadecan]-15'-ene-5,14'-dione
• Synonyms: (15α,16α,17α)-15,16-Dihydro-17-hydroxy-3-oxo-3'H-cyclopropa[15,16]pregna-4,15-diene-21-carboxylic Acid γ-Lactone; 15β,16β-Methylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone; 17β-Hydroxy-15β,16β-methylene-3-oxo-17α-pregn-4-ene-21-carboxylic Acid γ-Lactone; 6,7-Demethylene Drospirenone

Database IDs

• CAS Number: 67372-68-3
• PubChem SID: 162259909
• PubChem CID: 13505844

CALCULATED PROPERTIES

• Acid pKa: 19.083578
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.7010179
• LogD (pH = 7.4): 3.7010179
• Log P: 3.7010179
• Molar Refractivity: 98.9832 cm^3
• Polarizability: 39.3132 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Ethyl Acetate; Methanol

DETAILS

Toronto Research Chemicals - D231040

An intermediate in the synthesis of Drospirenone (D689500). Drospirenone impurity.

REFERENCES

• Nickisch, K., et al.: J. Med. Chem., 34, 2464 (1991)