methyl (1'R,2R,2'S,9'R,10'R,11'S,15'S,17'R)-2',15'-dimethyl-5,5'-dioxo-18'-oxaspiro[oxolane-2,14'-pentacyclo[8.8.0.0^{1,17}.0^{2,7}.0^{11,15}]octadecan]-6'-ene-9'-carboxylate

• ChemBase ID: 72789
• Molecular Formular: C24H30O6
• Molecular Mass: 414.4914
• Monoisotopic Mass: 414.20423868
• SMILES: C1C(=O)C=C2[C@](C1)([C@]13[C@@H]([C@@H](C2)C(=O)OC)[C@H]2[C@](C[C@@H]1O3)([C@@]1(CC2)CCC(=O)O1)C)C
• Canonical SMILES: COC(=O)[C@@H]1CC2=CC(=O)CC[C@@]2([C@@]23[C@@H]1[C@@H]1CC[C@]4([C@@]1(C)C[C@@H]3O2)CCC(=O)O4)C
• InChI: InChI=1S/C24H30O6/c1-21-7-4-14(25)10-13(21)11-15(20(27)28-3)19-16-5-8-23(9-6-18(26)30-23)22(16,2)12-17-24(19,21)29-17/h10,15-17,19H,4-9,11-12H2,1-3H3/t15-,16+,17-,19+,21+,22+,23-,24-/m1/s1
• InChIKey: JUKPWJGBANNWMW-VWBFHTRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1'R,2R,2'S,9'R,10'R,11'S,15'S,17'R)-2',15'-dimethyl-5,5'-dioxo-18'-oxaspiro[oxolane-2,14'-pentacyclo[8.8.0.0^{1,17}.0^{2,7}.0^{11,15}]octadecan]-6'-ene-9'-carboxylate
• IUPAC Traditional name: inspra
• Synonyms: Inspra; Epoxymexrenone; CGP30083; SC-66110; Eplerenone

Database IDs

• CAS Number: 107724-20-9
• PubChem SID: 162037710
• PubChem CID: 443872

CALCULATED PROPERTIES

• Acid pKa: 15.113572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.3314128
• LogD (pH = 7.4): 2.3314128
• Log P: 2.3314128
• Molar Refractivity: 106.6777 cm^3
• Polarizability: 42.67 Å^3
• Polar Surface Area: 82.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1707

Research Area: Cardiovascular Disease
Biological Activity:
Eplerenone is an aldosterone antagonist with an IC50 of 0.36 μM. It is used as an adjunct in the management of chronic heart failure. It is similar to the diuretic spironolactone, though it may be more specific for the mineralocorticoid receptor and is specifically marketed for reducing cardiovascular risk in patients following myocardial infarction. [1] 

REFERENCES

• http://en.wikipedia.org/wiki/Eplerenone