(1'R,2S,2'S,3'S,5'S,7'S,10'S,11'R,18'R)-18'-(acetylsulfanyl)-7',11'-dimethylspiro[oxolane-2,6'-pentacyclo[8.8.0.02,7.03,5.011,16]octadecane]-12',15'-diene-5,14'-dione

• ChemBase ID: 172696
• Molecular Formular: C25H30O4S
• Molecular Mass: 426.5683
• Monoisotopic Mass: 426.18648044
• SMILES: C1=C[C@]2(C(=CC1=O)C[C@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1[C@H]1[C@@H]([C@]32CCC(=O)O3)C1)C)SC(=O)C)C
• Canonical SMILES: CC(=O)S[C@@H]1CC2=CC(=O)C=C[C@@]2([C@@H]2[C@@H]1[C@@H]1[C@@H]3C[C@@H]3[C@]3([C@]1(CC2)C)CCC(=O)O3)C
• InChI: InChI=1S/C25H30O4S/c1-13(26)30-19-11-14-10-15(27)4-7-23(14,2)17-5-8-24(3)22(21(17)19)16-12-18(16)25(24)9-6-20(28)29-25/h4,7,10,16-19,21-22H,5-6,8-9,11-12H2,1-3H3/t16-,17+,18+,19-,21+,22+,23+,24+,25+/m1/s1
• InChIKey: CPHJTSJQUQZOLJ-ISIDMKFXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,2S,2'S,3'S,5'S,7'S,10'S,11'R,18'R)-18'-(acetylsulfanyl)-7',11'-dimethylspiro[oxolane-2,6'-pentacyclo[8.8.0.0^2,^7.0^3,^5.0^1^1,^1^6]octadecane]-12',15'-diene-5,14'-dione
• IUPAC Traditional name: (1'R,2S,2'S,3'S,5'S,7'S,10'S,11'R,18'R)-18'-(acetylsulfanyl)-7',11'-dimethylspiro[oxolane-2,6'-pentacyclo[8.8.0.0^2,^7.0^3,^5.0^1^1,^1^6]octadecane]-12',15'-diene-5,14'-dione
• Synonyms: (7α,15α,16α,17α)-7-(Acetylthio)-15,16-dihydro-17-hydroxy-3-oxo-3'H-cyclopropa[15,16]pregna-1,4,15-triene-21-carboxylic Acid γ-Lactone; ZK 94679; Mespirenone

Database IDs

• CAS Number: 87952-98-5
• PubChem SID: 164228606
• PubChem CID: 65660

CALCULATED PROPERTIES

• Acid pKa: 17.738825
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.3782754
• LogD (pH = 7.4): 3.3782754
• Log P: 3.3782754
• Molar Refractivity: 117.2146 cm^3
• Polarizability: 45.93847 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M225770

A new mineralocorticoid antagonist; has an inhibition effect on aldosterone-induced hypertension.

REFERENCES

• Hildebrand, M., et al.: Xenobiotica, 17, 623 (1987)
• Nishino, Y., et al.: Arzneim.-Forsch., 38, 1800 (1987)
• Zhao, Y., et al.: J. Pharm. Sci., 90, 749 (1987)
• Chiou, W., et al.: Pharm. Res., 19, 868 ( 2002),