2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl (2H31)hexadecanoate

• ChemBase ID: 166726
• Molecular Formular: C38H59FO6
• Molecular Mass: 630.8698632
• Monoisotopic Mass: 630.42956783
• 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)CCCCCCCCCCCCCCC)O)C)F)C
• Canonical SMILES: CCCCCCCCCCCCCCCC(=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)F
• InChI: InChI=1S/C38H59FO6/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-34(43)45-26-33(42)38(44)27(2)23-31-30-20-19-28-24-29(40)21-22-35(28,3)37(30,39)32(41)25-36(31,38)4/h21-22,24,27,30-32,41,44H,5-20,23,25-26H2,1-4H3/t27-,30+,31+,32+,35+,36+,37+,38+/m1/s1
• InChIKey: WDPYZTKOEFDTCU-WDJQFAPHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-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 (^2H₃₁)hexadecanoate
• IUPAC Traditional name: 2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-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 (^2H₃₁)hexadecanoate
• Synonyms: (11β,16α)-9-Fluoro-11,17-dihydroxy-16-methyl-21-[(1-oxohexadecyl-d31)oxy]pregna-1,4-diene-3,20-dione; Dexamethasone Palmitate-d31; Limethason-d31; Limethasone-d31; Lipotalon-d31; Dexamethasone 21-Palmitate-d31

Database IDs

• PubChem SID: 162260859
• PubChem CID: 71315855

CALCULATED PROPERTIES

• Acid pKa: 12.440789
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 8.602624
• LogD (pH = 7.4): 8.602619
• Log P: 8.602624
• Molar Refractivity: 176.0843 cm^3
• Polarizability: 69.15835 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D298832

A labelled orticosteroid prodrug for the treatment of eye disorders.

REFERENCES

• Benameur, H., et al.: J. Pharm. Pharmacol., 47, 812 (1995)
• Tauchi, Y., et al.: Biol. Pharm. Bull., 24, 925 (1995)
• Chono, S., et al.: J. Drug Targeting, 13, 407 (1995)