Showing Metabocard for 3-hydroxy-L-kynurenine (BASm0003215)

Common Name3-hydroxy-l-kynurenine
DescriptionL-3-Hydroxykynurenine (L-3-HK) is a metabolite in the kynurenine pathway, the major route of tryptophan degradation in mammals. Kynurenine 3-monooxygenase, an NADPH-dependent flavin monooxygenase, catalyses the hydroxylation of L-kynurenine to L-3-hydroxykynurenine. 3-hydroxykynurenine can be converted to 3-hydroxyanthranilate by the enzyme 3-hydroxykinureninase. It may also be converted to 4-(2-amino-3-hydroxphenyl)-2,4-dioxobutanoate by the enzyme kynurenine-oxoglutarate transaminase. L-3-Hydroxykynurenine (L-3-HK) is a known generator of highly reactive free radicals. An elevation of L-3-HK levels has been shown to constitute a significant hazard in situations of excitotoxic injury. In particular, L-3-HK may contribute to the neuronal deficits underlying HIV-associated dementia (PMID: 7830088 ). Pharmacological interventions aimed at decreasing L-3-HK formation may therefore be particularly useful for the treatment of neurological diseases which are associated with an abnormally enhanced flux through the kynurenine pathway (PMID: 10583474 ).
Structure
Molecular FormulaC10H12N2O4
Average Mass224.21330
Monoisotopic Mass224.07971
IUPAC Name(2S)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
Traditional Name3-hydroxy-l-kynurenine
CAS Registry Number606-14-4
SMILESNc1c(O)cccc1C(=O)C[C@H]([NH3+])C(=O)[O-]
InChI IdentifierInChI=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
InChI KeyVCKPUUFAIGNJHC-LURJTMIESA-N
CHEBI IDCHEBI:58125
HMDB IDHMDB0011631
Pathways
NameSMPDB/PathBank
Tryptophan metabolism
StateSolid
Water Solubility3.33e+00 g/l
logP-2.09
logS-1.83
pKa (Strongest Acidic)0.99
pKa (Strongest Basic)8.90
Hydrogen Acceptor Count6
Hydrogen Donor Count4
Polar Surface Area126.64 Ų
Rotatable Bond Count4
Physiological Charge0
Formal Charge0
Refractivity57.03 m³·mol⁻¹
Polarizability21.67

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