3-Hydroxykynurenine

3-Hydroxykynurenine is a metabolite of tryptophan, which filters UV light in the human lens.[1] It is one of two pigments identified as responsible for the goldenrod crab spider's (Misumena vatia) yellow coloration.

The Kynurenine pathway, which connects quinolinic acid to tryptophan. The pathway is named for the first intermediate, kynurenine, which is a precursor to kynurenic acid and 3-hydroxykynurenine.[2]
3-Hydroxykynurenine
Skeletal formula of 3-hydroxykynurenine
Ball-and-stick model of the 3-hydroxykynurenine molecule as a zwitterion
Names
IUPAC name
2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH 3-hydroxykynurenine
UNII
  • InChI=1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16) checkY
    Key: VCKPUUFAIGNJHC-UHFFFAOYSA-N checkY
  • InChI=1/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)
    Key: VCKPUUFAIGNJHC-UHFFFAOYAF
  • O=C(O)C(N)CC(=O)c1cccc(O)c1N
Properties
C10H12N2O4
Molar mass 224.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

References
  1. Malina, HZ; Martin, XD (1995). "Deamination of 3-hydroxykynurenine in bovine lenses: a possible mechanism of cataract formation in general". Graefes Arch Clin Exp Ophthalmol. 233 (1): 38–44. doi:10.1007/bf00177784. PMID 7721122. S2CID 25414197.
  2. Schwarcz, Robert; John P. Bruno; Paul J. Muchowski; Hui-Qiu Wu (July 2012). "Kynurenines in the Mammalian Brain: When Physiology Meets Pathology". Nature Reviews Neuroscience. 13 (7): 465–477. doi:10.1038/nrn3257. PMC 3681811. PMID 22678511.

See also


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