2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-bromo-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate

• ChemBase ID: 166076
• Molecular Formular: C28H37BrO7
• Molecular Mass: 565.49318
• Monoisotopic Mass: 564.17226552
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]([C@H](C2)C)(C(=O)COC(=O)CC)OC(=O)CC)C)Br)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]2CCC2=CC(=O)C=C[C@]12C)Br)C(=O)COC(=O)CC
• InChI: InChI=1S/C28H37BrO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1
• InChIKey: YXTPQNBZOYQVJP-XYWKZLDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-bromo-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
• IUPAC Traditional name: 2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-bromo-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
• Synonyms: (11β,16β)-9-Bromo-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dione; 9-Deschloro-9-bromo Beclomethasone Dipropionate

Database IDs

• CAS Number: 52092-14-5
• PubChem SID: 162260209
• PubChem CID: 70502239

CALCULATED PROPERTIES

• Acid pKa: 13.881541
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.6138873
• LogD (pH = 7.4): 4.6138873
• Log P: 4.6138873
• Molar Refractivity: 137.7763 cm^3
• Polarizability: 53.971684 Å^3
• Polar Surface Area: 106.97 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D288555

An impurity of Beclomethasone Dipropionate (B131030).

REFERENCES

• Shou, M. et al.: J. Pharmac. Biomed. Anal., 50, 356 (2009)
• Johnston, S. et al.: J. Chrom. Sci., 48, 733 (2009)