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

• ChemBase ID: 178583
• Molecular Formular: C22H30O3S
• Molecular Mass: 374.5368
• Monoisotopic Mass: 374.19156582
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)S)[C@H]2[C@](CC1)([C@]1(CC2)OC(=O)CC1)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C[C@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]12CCC(=O)O1)C)S)C
• InChI: InChI=1S/C22H30O3S/c1-20-7-3-14(23)11-13(20)12-17(26)19-15(20)4-8-21(2)16(19)5-9-22(21)10-6-18(24)25-22/h11,15-17,19,26H,3-10,12H2,1-2H3/t15-,16-,17+,19+,20-,21-,22+/m0/s1
• InChIKey: NZCDWYJROUPYPT-NYTLBARGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2R,2'R,9'R,10'R,11'S,15'S)-2',15'-dimethyl-9'-sulfanylspiro[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'R,10'R,11'S,15'S)-2',15'-dimethyl-9'-sulfanylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan]-6'-ene-5,5'-dione
• Synonyms: (7α,17α)-17-Hydroxy-7-mercapto-3-oxo-pregn-4-ene-21-carboxylic Acid γ-Lactone; 7α-Thiospirolactone; Deacetylspironolactone; Mercaptospironolactone; SC 24813; 7α-Thio Spironolactone

Database IDs

• CAS Number: 38753-76-6
• PubChem SID: 164234493
• PubChem CID: 119472

CALCULATED PROPERTIES

• Acid pKa: 9.996487
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.7961342
• LogD (pH = 7.4): 3.7951279
• Log P: 3.796147
• Molar Refractivity: 104.0365 cm^3
• Polarizability: 41.258163 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T375000

A metabolite of Spironolactone.

REFERENCES

• Morris, R., et al.: Eur. J. Clin. Pharmacol., 34, 233 (1988)
• Dasgupta, A., et al.: Am. J. Clin. Pathol., 111, 406 (1999)