(1'R,2S,2'S,3'S,5'S,7'S,10'S,11'R,18'S)-18'-(chloromethyl)-7',11'-dimethylspiro[oxolane-2,6'-pentacyclo[8.8.0.02,7.03,5.011,16]octadecan]-15'-ene-5,14'-dione

• ChemBase ID: 164344
• Molecular Formular: C24H31ClO3
• Molecular Mass: 402.95414
• Monoisotopic Mass: 402.19617253
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H]([C@H](C2)CCl)[C@H]2[C@](CC1)([C@@]1([C@@H]3[C@H]2C3)CCC(=O)O1)C)C
• Canonical SMILES: ClC[C@H]1CC2=CC(=O)CC[C@@]2([C@@H]2[C@@H]1[C@@H]1[C@@H]3C[C@@H]3[C@]3([C@]1(CC2)C)CCC(=O)O3)C
• InChI: InChI=1S/C24H31ClO3/c1-22-6-3-15(26)10-14(22)9-13(12-25)20-17(22)4-7-23(2)21(20)16-11-18(16)24(23)8-5-19(27)28-24/h10,13,16-18,20-21H,3-9,11-12H2,1-2H3/t13-,16-,17+,18+,20-,21+,22+,23+,24+/m1/s1
• InChIKey: YGBFZJNESAZJNB-MQSRJSRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,2S,2'S,3'S,5'S,7'S,10'S,11'R,18'S)-18'-(chloromethyl)-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'S,3'S,5'S,7'S,10'S,11'R,18'S)-18'-(chloromethyl)-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: 7β-(Chloromethyl)-15β,16β-methylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone; (7β,15α,16α,17α)-7-(Chloromethyl)-15,16-dihydro-17-hydroxy-3-oxo-3'H-cyclopropa[15,16]pregna-4,15-diene-21-carboxylic Acid γ-Lactone; 7-Chloromethyl Drospirenone

Database IDs

• CAS Number: 932388-90-4
• PubChem SID: 162258479
• PubChem CID: 71314744

CALCULATED PROPERTIES

• Acid pKa: 18.38936
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.983904
• LogD (pH = 7.4): 3.983904
• Log P: 3.983904
• Molar Refractivity: 108.4345 cm^3
• Polarizability: 42.98483 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C366980

One of the two epimeric lactones from Drospirenone (D689500) acidic treatment. Drospirenone impurity.

REFERENCES

• Solo, A., et al.: J. Med. Chem., 9, 179 (1966)
• Bakshi, M., et l.: J. Pharm. Biomed. Anal., 28, 1011 (1966)