(1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.02,7.011,15]heptadecane]-6',8'-diene-5,5'-dione

• ChemBase ID: 163597
• Molecular Formular: C22H28O3
• Molecular Mass: 340.45592
• Monoisotopic Mass: 340.20384476
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C=C2)[C@H]2[C@](CC1)([C@]1(CC2)OC(=O)CC1)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]12CCC(=O)O1)C)C
• InChI: InChI=1S/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1
• InChIKey: UJVLDDZCTMKXJK-WNHSNXHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-6',8'-diene-5,5'-dione
• IUPAC Traditional name: canrenone
• Synonyms: (17α)-17-Hydroxy-3-oxo-pregna-4,6-diene-21-carboxylic Acid γ-Lactone; 17α-2-Carboxyethyl-17β-hydroxyandrosta-4,6-dien-3-one Lactone; Phanurane; Canrenone; (1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione

Database IDs

• CAS Number: 976-71-6
• MDL Number: MFCD00071735
• PubChem SID: 162257732
• PubChem CID: 13789

CALCULATED PROPERTIES

• Acid pKa: 19.93863
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.5953987
• LogD (pH = 7.4): 3.5953987
• Log P: 3.5953987
• Molar Refractivity: 97.4828 cm^3
• Polarizability: 37.95804 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Methanol
• Apperance: Pale yellow to pale Green Solid
• Melting Point: 158-160°C
• Hydrophobicity(logP): 2.906

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 95%

DETAILS

Toronto Research Chemicals - C175610

Aldosterone antagonist. Diuretic.

REFERENCES

• Sadee, W., et al.: J. Pharmacol. Exp. Ther., 185, 686 (1973)
• Pitt, B., et al.: Circulation, 108, 1831 (1973)
• Silvestre, J., et al.: J. Biol. Chem., 273, 4883 (1973)
• Struthers, A., et al.: Heart, 92, 1728 (1973)