sodium 2-{[(2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxytrideca-4,6,10-trien-8-yn-1-yl]oxy}acetate

• ChemBase ID: 179643
• Molecular Formular: C21H22FNaO7
• Molecular Mass: 428.3833532
• Monoisotopic Mass: 428.12472555
• SMILES: c1c(ccc(c1)OC[C@H](/C=C/C#C/C=C/C=C/[C@H]([C@H](COCC(=O)[O-])O)O)O)F.[Na+]
• Canonical SMILES: [O-]C(=O)COC[C@@H]([C@@H](/C=C/C=C/C#C/C=C/[C@@H](COc1ccc(cc1)F)O)O)O.[Na+]
• InChI: InChI=1S/C21H23FO7.Na/c22-16-9-11-18(12-10-16)29-13-17(23)7-5-3-1-2-4-6-8-19(24)20(25)14-28-15-21(26)27;/h2,4-12,17,19-20,23-25H,13-15H2,(H,26,27);/q;+1/p-1/b4-2+,7-5+,8-6+;/t17-,19+,20-;/m0./s1
• InChIKey: JEZLFWXSKCTMPN-ILCIQDJASA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2-{[(2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxytrideca-4,6,10-trien-8-yn-1-yl]oxy}acetate
• IUPAC Traditional name: sodium 2-{[(2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxytrideca-4,6,10-trien-8-yn-1-yl]oxy}acetate
• Synonyms: 2-[[(2S,3R,4E,6E,10E,12S)-13-(4-Fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-yn-1-yl]oxy]acetic Acid Sodium Salt; ZK-192; ZK-994

Database IDs

• CAS Number: 686773-12-6
• PubChem SID: 164235553
• PubChem CID: 24744011

CALCULATED PROPERTIES

• Acid pKa: 3.807836
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.14085704
• LogD (pH = 7.4): -1.7049967
• Log P: 1.5537704
• Molar Refractivity: 118.1095 cm^3
• Polarizability: 39.527695 Å^3
• Polar Surface Area: 119.28 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Z485900

ZK-994 is a β-oxidation-resistant lipoxin A4 receptor agonist. ZK-994 is used to treat hapten-induced colitis by attenuating inflammation and immune dysfunction.

REFERENCES

• Fiorucci, S. et al.: Proc. Nat. Acad. Sci. USA, 101, 15736 (2004)
• Levy, B.D. et al.: FASEB J., 21, 3877 (2004)