(1S,2R,10S,11S,13R,14S,15S,17S)-17-hydroxy-2,13,14,15-tetramethyl-14-propanoyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 177528
• Molecular Formular: C24H34O3
• Molecular Mass: 370.52496
• Monoisotopic Mass: 370.25079495
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1C[C@H]([C@@]2(C(=O)CC)C)C)C)O)C
• Canonical SMILES: CCC(=O)[C@@]1(C)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C24H34O3/c1-6-20(27)24(5)14(2)11-18-17-8-7-15-12-16(25)9-10-22(15,3)21(17)19(26)13-23(18,24)4/h9-10,12,14,17-19,21,26H,6-8,11,13H2,1-5H3/t14-,17+,18+,19+,21-,22+,23+,24-/m1/s1
• InChIKey: QTTRZHGPGKRAFB-OOKHYKNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,13R,14S,15S,17S)-17-hydroxy-2,13,14,15-tetramethyl-14-propanoyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: rimexolone
• Synonyms: (11β,16α,17β)-11-Hydroxy-16,17-dimethyl-17-(1-oxopropyl)androsta-1,4-dien-3-one; 11β-Hydroxy-16α,17,21-trimethylpregna-1,4-diene-3,20-dione; 11β-Hydroxy-16α,17α,21-trimethyl-5α-pregna-1,4-diene-3,20-dione; Org 6216; Rimexel; Rimexolone; Trimexolone; Vexol; Rimexolone

Database IDs

• CAS Number: 49697-38-3
• PubChem SID: 164233438
• PubChem CID: 5311412

CALCULATED PROPERTIES

• Acid pKa: 18.761986
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.381233
• LogD (pH = 7.4): 4.3812323
• Log P: 4.3812323
• Molar Refractivity: 109.0676 cm^3
• Polarizability: 42.29908 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R422500

Anti-inflammatory (local).

REFERENCES

• Fox, P.K., et al.: Arzneim.-Forsch., 30, 55 (1980)
• Gevers, G., et al.: Clin. Rheumatol., 13, 103 (1980)