(2R,2'S,10'R,11'S,15'S)-2',15'-dimethyl-5,5'-dioxospiro[oxolane-2,14'-tetracyclo[8.7.0.02,7.011,15]heptadecane]-1'(17'),6'-diene-9'-carboxylic acid

• ChemBase ID: 163633
• Molecular Formular: C23H28O5
• Molecular Mass: 384.46542
• Monoisotopic Mass: 384.193674
• SMILES: C1CC(=O)C=C2[C@]1(C1=CC[C@]3([C@H]([C@@H]1C(C2)C(=O)O)CC[C@@]13OC(=O)CC1)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC([C@@H]1C2=CC[C@]2([C@H]1CC[C@]12CCC(=O)O1)C)C(=O)O)C
• InChI: InChI=1S/C23H28O5/c1-21-7-3-14(24)11-13(21)12-15(20(26)27)19-16(21)4-8-22(2)17(19)5-9-23(22)10-6-18(25)28-23/h4,11,15,17,19H,3,5-10,12H2,1-2H3,(H,26,27)/t15?,17-,19+,21-,22-,23+/m0/s1
• InChIKey: PORDWKGOVBSUDI-KEQYVETGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,2'S,10'R,11'S,15'S)-2',15'-dimethyl-5,5'-dioxospiro[oxolane-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-1'(17'),6'-diene-9'-carboxylic acid
• IUPAC Traditional name: (2R,2'S,10'R,11'S,15'S)-2',15'-dimethyl-5,5'-dioxospiro[oxolane-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-1'(17'),6'-diene-9'-carboxylic acid
• Synonyms: 17α-Hydroxy-3-oxo-pregna-4,9(11)-diene-7,21-dicarboxylic Acid γ-Lactone; 7-Carboxy-9(11)Δ-canrenone

Database IDs

• PubChem SID: 162257768
• PubChem CID: 71314507

CALCULATED PROPERTIES

• Acid pKa: 4.366774
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.6121644
• LogD (pH = 7.4): -0.13890582
• Log P: 2.7744853
• Molar Refractivity: 103.4561 cm^3
• Polarizability: 40.34051 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol; Tetrahydrofuran
• Apperance: Orange Solid

DETAILS

Toronto Research Chemicals - C177830

Intermediate in the preparation of Eplerenone and its derivatives.