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

• ChemBase ID: 161172
• Molecular Formular: C25H33ClO6
• Molecular Mass: 464.97892
• Monoisotopic Mass: 464.19656646
• 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)CO)OC(=O)CC)C)Cl)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)Cl)C(=O)CO
• InChI: InChI=1S/C25H33ClO6/c1-5-21(31)32-25(20(30)13-27)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,26)19(29)12-23(18,25)4/h8-9,11,14,17-19,27,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1
• InChIKey: OHYGPBKGZGRQKT-XGQKBEPLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-17-hydroxy-14-(2-hydroxyacetyl)-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,10S,11S,13S,14R,15S,17S)-1-chloro-17-hydroxy-14-(2-hydroxyacetyl)-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: (11β,16β)-9-Chloro-11,21-dihydroxy-16-methyl-17-(1-oxopropoxy)-pregna-1,4-diene-3,20-dione; Beclomethasone 17-Monopropionate; Beclomethasone 17-Propionate

Database IDs

• CAS Number: 5534-18-9
• PubChem SID: 162255307
• PubChem CID: 62965

CALCULATED PROPERTIES

• Acid pKa: 13.516661
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.286731
• LogD (pH = 7.4): 3.2867308
• Log P: 3.286731
• Molar Refractivity: 121.0144 cm^3
• Polarizability: 47.417023 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 119-120°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B131050

Active metabolite of Beclomethasone Dipropionate (BDP).

REFERENCES

• Soria, I., et al.: Biopharm. Drug Dispos., 19, 297 (1998)
• Harrison, L., et al., J. Pharm. Pharmacol., 51, 1235 (1998)
• Daley-Yates, P., et al.: Br. J. Clin. Pharm., 51, 400 (2001).