(1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 164859
• Molecular Formular: C22H28ClFO4
• Molecular Mass: 410.9067232
• Monoisotopic Mass: 410.16601528
• SMILES: C1=C[C@]2(C(=CC1=O)[C@H](C[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H]([C@@H]2C(=O)CO)C)C)O)Cl)F)C
• Canonical SMILES: OCC(=O)[C@H]1[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F)Cl
• InChI: InChI=1S/C22H28ClFO4/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-21(15,3)22(14,23)18(28)9-20(13,2)19(11)17(27)10-25/h4-5,7,11,13-14,16,18-19,25,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,18+,19-,20+,21+,22+/m1/s1
• InChIKey: YMTMADLUXIRMGX-RFPWEZLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: clocortolona
• Synonyms: (6α,11β,16α)-9-Chloro-6-fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione; 9-Chloro-6α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione; 9-Chloro-6α-fluoro-11β,21-dihydroxy-17α-methylpregna-1,4-diene-3,20-dione; 9-Chloro-6α-fluoro-16α-methyl-1,4-pregnadiene-11β,21-diol-3,20-dione; Clorcortelone; Clocortolone

Database IDs

• CAS Number: 4828-27-7
• PubChem SID: 162258993
• PubChem CID: 5311052

CALCULATED PROPERTIES

• Acid pKa: 13.533641
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.4748218
• LogD (pH = 7.4): 2.4748216
• Log P: 2.4748218
• Molar Refractivity: 105.7364 cm^3
• Polarizability: 40.834625 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C583800

Corticosteroid used in the treatment of skin inflammmation and other skin conditions arising for dermatoses.

REFERENCES

• Rehm, K. et al.: Pharmaz. Zeit., 127, 888 (1982)