(1R,2S,10S,11S,13S,14R,15S,17S)-14-[2-chloro(2H2)acetyl]-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl(6,8,8-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 164856
• Molecular Formular: C22H28ClFO4
• Molecular Mass: 410.9067232
• Monoisotopic Mass: 410.16601528
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]([C@@]2(C(=O)CCl)O)C)C)O)F)C
• Canonical SMILES: ClCC(=O)[C@@]1(O)[C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
• InChIKey: FCSHDIVRCWTZOX-DVTGEIKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S,17S)-14-[2-chloro(^2H₂)acetyl]-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1R,2S,10S,11S,13S,14R,15S,17S)-14-[2-chloro(^2H₂)acetyl]-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: 21-Chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione-d5; Clobetasol-d5; (11β,16β)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione-d5

Database IDs

• PubChem SID: 162258990
• PubChem CID: 71314918

CALCULATED PROPERTIES

• Acid pKa: 12.468411
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.0361614
• LogD (pH = 7.4): 3.0361578
• Log P: 3.0361614
• Molar Refractivity: 105.5439 cm^3
• Polarizability: 40.829803 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C583492

Labelled Clobetasol. Topical corticosteroid. Glucocorticoid; anti-inflammatory.

REFERENCES

• Olsen, E.A., et al.: J. Am. Acad. Dermatol., 15, 246 (1986)