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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: 3-hydroxy-L-kynurenine

Synonyms: L-3-hydroxykynurenine, 3-hydroxy-kynurenine

Superclasses: an amino acid or its derivative an amino acid a modified amino acid a hydroxylated amino acid a hydroxy-L-amino acid

Chemical Formula: C10H12N2O4

Molecular Weight: 224.22 Daltons

Monoisotopic Molecular Weight: 224.079706884 Daltons

SMILES: C([O-])(=O)C([N+])CC(=O)C1(=C(N)C(O)=CC=C1)

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)/t6-/m0/s1

InChIKey: InChIKey=VCKPUUFAIGNJHC-LURJTMIESA-N

Unification Links: CAS:606-14-4 , ChEBI:58125 , HMDB:HMDB11631 , KEGG:C02794 , MetaboLights:MTBLC58125 , PubChem:25244175

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 6.8334436 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

tryptophan degradation to 2-amino-3-carboxymuconate semialdehyde , tryptophan degradation XI (mammalian, via kynurenine) :
3-hydroxy-L-kynurenine + H2O → 3-hydroxyanthranilate + L-alanine + H+

Reactions known to produce the compound:

tryptophan degradation to 2-amino-3-carboxymuconate semialdehyde , tryptophan degradation XI (mammalian, via kynurenine) :
L-kynurenine + NADPH + oxygen + H+3-hydroxy-L-kynurenine + NADP+ + H2O

Reactions known to both consume and produce the compound:

tryptophan degradation XI (mammalian, via kynurenine) :
3-hydroxy-L-kynurenine + 2-oxoglutarate ↔ 4-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoate + L-glutamate

In Reactions of unknown directionality:

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Enzymes inhibited by 3-hydroxy-L-kynurenine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: tryptophan dioxygenase [Hitchcock88]

Credits:
Revised 28-Jul-2013 by Caspi R , SRI International


References

Hitchcock88: Hitchcock MJ, Katz E (1988). "Purification and characterization of tryptophan dioxygenase from Streptomyces parvulus." Arch Biochem Biophys 261(1);148-60. PMID: 3341771

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, biocyc14.