(1R,2S,10S,11S,13S,14R,15S)-14-(2-chloroacetyl)-1-fluoro-2,13,15-trimethyl-5,17-dioxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl (2H7)butanoate

• ChemBase ID: 164858
• Molecular Formular: C26H32ClFO5
• Molecular Mass: 478.9806832
• Monoisotopic Mass: 478.19223002
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2(C(=O)C[C@]2([C@H]1C[C@@H]([C@@]2(C(=O)CCl)OC(=O)CCC)C)C)F)C
• Canonical SMILES: CCCC(=O)O[C@@]1([C@@H](C)C[C@@H]2[C@]1(C)CC(=O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F)C(=O)CCl
• InChI: InChI=1S/C26H32ClFO5/c1-5-6-22(32)33-26(21(31)14-27)15(2)11-19-18-8-7-16-12-17(29)9-10-23(16,3)25(18,28)20(30)13-24(19,26)4/h9-10,12,15,18-19H,5-8,11,13-14H2,1-4H3/t15-,18-,19-,23-,24-,25-,26-/m0/s1
• InChIKey: FBRAWBYQGRLCEK-AVVSTMBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S)-14-(2-chloroacetyl)-1-fluoro-2,13,15-trimethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl (^2H₇)butanoate
• IUPAC Traditional name: (1R,2S,10S,11S,13S,14R,15S)-14-(2-chloroacetyl)-1-fluoro-2,13,15-trimethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl (^2H₇)butanoate
• Synonyms: (16β)-21-Chloro-9-fluoro-16-methyl-17-(1-oxobutoxy-7)pregna-1,4-diene-3,11,20-trione; CCl 5537-d7; Clobetasone-d7 17-Butyrate; Emovate-d7; Eumovate-d7; GR 2/1214-d7; Kindavate-d7; Molivate-d7; SN 203-d7; Clobetasone 17-Butyrate-d7

Database IDs

• PubChem SID: 162258992
• PubChem CID: 71314920

CALCULATED PROPERTIES

• Acid pKa: 15.088956
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 5.1859193
• LogD (pH = 7.4): 5.1859193
• Log P: 5.1859193
• Molar Refractivity: 123.101 cm^3
• Polarizability: 47.80599 Å^3
• Polar Surface Area: 77.51 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C583552

Labelled Clobetasone (C583550). Glucocorticoid; anti-inflammmatory.

REFERENCES

• Tamura, J., et al.: J. Toxicol. Sci., 5, 45 (1980)