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3-Hydroxykynurenine

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3-Hydroxykynurenine
Names


IUPAC name 2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
Identifiers
CAS Number	484-78-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:1547^Y
ChEMBL	ChEMBL442576^Y
ChemSpider	87^Y
KEGG	C02794^Y
MeSH	3-hydroxykynurenine
PubChem CID	89
UNII	27723548JL^Y
CompTox Dashboard(EPA)	DTXSID00862009
InChI 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)^Y Key: VCKPUUFAIGNJHC-UHFFFAOYSA-N^Y 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
SMILES O=C(O)C(N)CC(=O)c1cccc(O)c1N
Properties
Chemical formula	C₁₀H₁₂N₂O₄
Molar mass	224.21 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

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

TheKynurenine pathway, which connectsquinolinic acid to tryptophan. The pathway is named for the first intermediate,kynurenine, which is a precursor tokynurenic acid and 3-hydroxykynurenine.^[2]

References

[edit]

^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.
^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.

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→	N′-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→
citrate

glycine→ serine→	3-Phosphoglyceric acid glycine→creatine:Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione:γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid
isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA
methionine→	generation of homocysteine:S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine:Cystathionine α-Ketobutyric acid +Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA