(1'S,2R,2'R,9'S,10'R,11'S,15'S)-9'-(acetylsulfanyl)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.02,7.011,15]heptadecan]-6'-ene-5,5'-dione

• ChemBase ID: 177856
• Molecular Formular: C24H32O4S
• Molecular Mass: 416.57348
• Monoisotopic Mass: 416.2021305
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H]([C@H](C2)SC(=O)C)[C@H]2[C@](CC1)([C@]1(CC2)OC(=O)CC1)C)C
• Canonical SMILES: CC(=O)S[C@H]1CC2=CC(=O)CC[C@@]2([C@@H]2[C@@H]1[C@@H]1CC[C@]3([C@]1(CC2)C)CCC(=O)O3)C
• InChI: InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19-,21+,22-,23-,24+/m0/s1
• InChIKey: LXMSZDCAJNLERA-KVXIHFSQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2R,2'R,9'S,10'R,11'S,15'S)-9'-(acetylsulfanyl)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan]-6'-ene-5,5'-dione
• IUPAC Traditional name: (1'S,2R,2'R,9'S,10'R,11'S,15'S)-9'-(acetylsulfanyl)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan]-6'-ene-5,5'-dione
• Synonyms: (7β,17α)-7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic Acid γ-Lactone; 17-Hydroxy-7β-mercapto-3-oxo-17α-pregn-4-ene-21-carboxylic Acid γ-Lactone Acetate; 3'-(3-Oxo-7β-acetylthio-17β-hydroxyandrost-4-en-17α-yl)-propionic Acid Lactone; 7β-(Acetylthio)-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic Acid γ-Lactone; SC 11940; 7β-Spironolactone

Database IDs

• CAS Number: 33784-05-3
• PubChem SID: 164233766
• PubChem CID: 11509929

CALCULATED PROPERTIES

• Acid pKa: 18.006086
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.6367545
• LogD (pH = 7.4): 3.6367545
• Log P: 3.6367545
• Molar Refractivity: 113.5043 cm^3
• Polarizability: 45.06745 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S683010

7β-Spironolactone is the 7β-isomer of Spironolactone (S683000). It binds effectively to human plasma proteins.

REFERENCES

• Chien, Y.W. et al.: J. Pharmac. Sci., 65, 1337 (1976)