2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl (2H5)propanoate

• ChemBase ID: 161175
• 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)COC(=O)CC)O)C)Cl)C
• Canonical SMILES: CCC(=O)OCC(=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)Cl
• InChI: InChI=1S/C25H33ClO6/c1-5-21(30)32-13-20(29)25(31)14(2)10-18-17-7-6-15-11-16(27)8-9-22(15,3)24(17,26)19(28)12-23(18,25)4/h8-9,11,14,17-19,28,31H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1
• InChIKey: OPNPEZLXXKGRTA-XGQKBEPLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl (^2H₅)propanoate
• IUPAC Traditional name: 2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl (^2H₅)propanoate
• Synonyms: (11β,16β)-9-Chloro-11,17-dihydroxy-16-methyl-21-(1-oxopropoxy)-pregna-1,4-diene-3,20-dione-d5; Beclomethasone 21-Monopropionate-d5; Beclomethasone 21-Propionate-d5

Database IDs

• PubChem SID: 162255310
• PubChem CID: 71313648

CALCULATED PROPERTIES

• Acid pKa: 12.451898
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.286731
• LogD (pH = 7.4): 3.2867272
• 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

DETAILS

Toronto Research Chemicals - B131057

A labelled metabolite of Beclomethasone Dipropionate (BDP).

REFERENCES

• Foe, K., et al.: Biopharm. Drug Disposition, 19, 1 (1998)
• Harrison, L., et al.: Eur. J. Clin. Pharmacol., 58, 197 (1998)