(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl propanoate

• ChemBase ID: 169827
• Molecular Formular: C25H31ClF2O5
• Molecular Mass: 484.9604464
• Monoisotopic Mass: 484.18280821
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](C[C@@H]2F)[C@H]2[C@](C[C@@H]1O)([C@@]([C@H](C2)C)(OC(=O)CC)C(=O)CCl)C)F)C
• Canonical SMILES: CCC(=O)O[C@@]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)F)C(=O)CCl
• InChI: InChI=1S/C25H31ClF2O5/c1-5-21(32)33-25(20(31)12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15-,16-,18-,19-,22-,23-,24-,25-/m0/s1
• InChIKey: BDSYKGHYMJNPAB-LICBFIPMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl propanoate
• IUPAC Traditional name: (1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl propanoate
• Synonyms: (6α,11β,16β)-21-Chloro-6,9-difluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dione; Miracorten; Ulobetasol propionate; Ultravate; Halobetasol Propionate

Database IDs

• CAS Number: 66852-54-8
• PubChem SID: 162263959
• PubChem CID: 6918178

CALCULATED PROPERTIES

• Acid pKa: 13.545719
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.8381035
• LogD (pH = 7.4): 3.8381033
• Log P: 3.8381035
• Molar Refractivity: 119.1457 cm^3
• Polarizability: 46.300114 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White Solid
• Melting Point: 213-215°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - H102300

Anti-inflammatory; a dermatologic agent commonly used to treat psoriasis

REFERENCES

• Pearce, D., et al.: Int. J. Dermatol., 45, 370 (2006)