(2R,2'R,10'R,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: 179690
• Molecular Formular: C22H28O3
• Molecular Mass: 340.45592
• Monoisotopic Mass: 340.20384476
• SMILES: [C@@]12(C(=CC(=O)CC2)C=C[C@@H]2C1CC[C@@]1([C@@]3(OC(=O)CC3)CCC21)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C=C[C@@H]1C2CC[C@]2(C1CC[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-KUGJOEFMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,2'R,10'R,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: (2R,2'R,10'R,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
• Synonyms: Contaren; Luvion; Phanurane; Spiroletan; Canrenone

Database IDs

• CAS Number: 976-71-6
• PubChem SID: 164235600
• PubChem CID: 16401118

CALCULATED PROPERTIES

• Polarizability: 37.95804 Å^3
• 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
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Aldosterone antagonist

Product Information

• Application(s): Diuretic

REFERENCES

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• Ramsay, L.E. et al., Br. J. Clin. Pharmacol., 1976, 3, 607, (metab, pharmacol)
• Weeks, C.M. et al., Cryst. Struct. Commun., 1976, 5, 271, (cryst struct)
• Williamson, D.E., J. Pharm. Sci., 1976, 65, 138, (hplc, chromatog)
• Boreham, D.R. et al., Org. Mass Spectrom., 1979, 14, 442, (ms)
• Hickey, J.P. et al., J. Magn. Reson., 1980, 38, 501, (cmr)
• Highet, R.J. et al., Steroids, 1980, 35, 119, (cmr)
• Johnson, W.S. et al., J.A.C.S., 1982, 104, 3510, (synth, ()-form)
• Kojima, K. et al., J. Pharmacobio-Dyn., 1985, 8, 161
• Karim, A. et al., Curr. Clin. Pract. Ser., 1986, 35, 22; 47, (rev, pharmacol, metab)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 812