1.0 2011-09-21 01:38:04 UTC 2015-07-21 06:59:23 UTC FDB028330 L-3-Hydroxykynurenine L-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) [HMDB] (2S)-2-amino-4-(2-amino-3-Hydroxyphenyl)-4-oxobutanoate (2S)-2-amino-4-(2-amino-3-Hydroxyphenyl)-4-oxobutanoic acid 3-(2-amino-3-hydroxybenzoyl)-L-alanine L-3-HK C10H12N2O4 224.2133 224.079706882 (2S)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid 3-hydroxy-L-kynurenine 606-14-4 N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(O)=O 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 VCKPUUFAIGNJHC-LURJTMIESA-N belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Alkyl-phenylketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Amino acids Aniline and substituted anilines Aryl alkyl ketones Benzoyl derivatives Beta-amino ketones Butyrophenones Carboxylic acids Gamma-keto acids and derivatives Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Vinylogous amides o-Aminophenols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl-phenylketone Alpha-amino acid Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Aminophenol Aniline or substituted anilines Aromatic homomonocyclic compound Aryl alkyl ketone Benzenoid Benzoyl Beta-aminoketone Butyrophenone Carboxylic acid Carboxylic acid derivative Gamma-keto acid Hydrocarbon derivative Keto acid L-alpha-amino acid Monocarboxylic acid or derivatives Monocyclic benzene moiety O-aminophenol Organic nitrogen compound Organic oxide Organonitrogen compound Organopnictogen compound Phenol Primary aliphatic amine Primary amine Vinylogous amide 3-hydroxykynurenine Solid logp -2.09 ALOGPS logs -1.83 ALOGPS solubility 3.33e+00 g/l ALOGPS logp -2.2 ChemAxon pka_strongest_acidic 0.99 ChemAxon pka_strongest_basic 8.9 ChemAxon iupac (2S)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid ChemAxon average_mass 224.2133 ChemAxon mono_mass 224.079706882 ChemAxon smiles N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(O)=O ChemAxon formula C10H12N2O4 ChemAxon 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 ChemAxon inchikey VCKPUUFAIGNJHC-LURJTMIESA-N ChemAxon polar_surface_area 126.64 ChemAxon refractivity 57.03 ChemAxon polarizability 21.67 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Tryptophan Metabolism SMP00063 map00380 Specdb::CMs 2446 Specdb::CMs 39731 Specdb::CMs 159048 Specdb::MsMs 72534 Specdb::MsMs 72535 Specdb::MsMs 72536 Specdb::MsMs 131490 Specdb::MsMs 131491 Specdb::MsMs 131492 Specdb::MsMs 2713897 Specdb::MsMs 2713898 Specdb::MsMs 2713899 Specdb::MsMs 2964873 Specdb::MsMs 2964874 Specdb::MsMs 2964875 Specdb::NmrOneD 93612 Specdb::NmrOneD 93613 Specdb::NmrOneD 93614 Specdb::NmrOneD 93615 Specdb::NmrOneD 93616 Specdb::NmrOneD 93617 Specdb::NmrOneD 93618 Specdb::NmrOneD 93619 Specdb::NmrOneD 93620 Specdb::NmrOneD 93621 Specdb::NmrOneD 93622 Specdb::NmrOneD 93623 Specdb::NmrOneD 93624 Specdb::NmrOneD 93625 Specdb::NmrOneD 93626 Specdb::NmrOneD 93627 Specdb::NmrOneD 93628 Specdb::NmrOneD 93629 Specdb::NmrOneD 93630 Specdb::NmrOneD 93631 HMDB11631 17380 #<Reference:0x000055ce324a73f0> #<Reference:0x000055ce324a71c0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Kynurenine--oxoglutarate transaminase 1 Q16773 CCBL1 Kynurenine--oxoglutarate transaminase 3 Q6YP21 CCBL2 Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT