MiMeDB: Showing metabocard for L-3-Hydroxykynurenine (MMDBc0032921)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:27:26 UTC

Update Date

2024-04-30 19:55:01 UTC

Metabolite ID

MMDBc0032921

Metabolite Identification

Common Name

L-3-Hydroxykynurenine

Description

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 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241201482D          

 16 16  0  0  1  0            999 V2000
    9.5708   -8.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5708   -8.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8563   -7.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8563   -9.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1418   -8.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1418   -8.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8563  -10.1087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2853   -9.2837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2853   -7.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9997   -8.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7142   -7.6337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4287   -8.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1432   -7.6337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4287   -8.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7142   -6.8087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2853   -6.8087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  0  0  0  0
  9  1  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  2  0  0  0  0
 11 15  1  6  0  0  0
 16  9  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032921

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(O)=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
VCKPUUFAIGNJHC-LURJTMIESA-N

> <FORMULA>
C10H12N2O4

> <MOLECULAR_WEIGHT>
224.2133

> <EXACT_MASS>
224.079706882

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
21.667920358228034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid

> <ALOGPS_LOGP>
-2.09

> <JCHEM_LOGP>
-2.212526806637731

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.856351637136484

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.986621703292279

> <JCHEM_PKA_STRONGEST_BASIC>
8.90351767222249

> <JCHEM_POLAR_SURFACE_AREA>
126.64000000000001

> <JCHEM_REFRACTIVITY>
57.0311

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-L-kynurenine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      17.865 -15.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.865 -16.560   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.532 -14.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.532 -17.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.198 -15.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.198 -16.560   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      16.532 -18.870   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      19.199 -17.330   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      19.199 -14.250   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.533 -15.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.867 -14.250   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.200 -15.020   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      24.534 -14.250   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      23.200 -16.560   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      21.867 -12.710   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      19.199 -12.710   0.000  0.00  0.00           O+0
CONECT    1    2    3    9                                                  
CONECT    2    1    4    8                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6    7                                                  
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    4                                                            
CONECT    8    2                                                            
CONECT    9    1   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11                                                            
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0011631
HETATM    1  N1  UNL     1       2.385   1.741   0.676  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.127   0.423   0.163  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.150  -0.499   0.149  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.392  -0.118   0.632  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.959  -1.782  -0.333  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.714  -2.142  -0.809  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.691  -1.201  -0.789  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.869   0.080  -0.311  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.197   1.053  -0.289  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.022   2.198   0.162  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.536   0.685  -0.801  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.429   0.241   0.335  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.919  -0.893   1.036  1.00  0.00           N  
HETATM   14  C10 UNL     1      -3.798  -0.034  -0.160  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.376  -1.120   0.038  1.00  0.00           O  
HETATM   16  O4  UNL     1      -4.426   0.994  -0.870  1.00  0.00           O  
HETATM   17  H1  UNL     1       2.414   2.497  -0.055  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.532   1.953   1.667  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.580   0.790   0.989  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.790  -2.495  -0.332  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.539  -3.134  -1.190  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.278  -1.519  -1.171  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.544  -0.018  -1.630  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.968   1.642  -1.212  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.508   1.090   1.045  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.361  -0.687   1.870  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.539  -1.705   1.083  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.281   1.959  -0.587  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3    3    8
CONECT    3    4    5
CONECT    4   19
CONECT    5    6    6   20
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   23   24
CONECT   12   13   14   25
CONECT   13   26   27
CONECT   14   15   15   16
CONECT   16   28
END

Synonyms

Value	Source
(2S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid	ChEBI
3-(3-Hydroxyanthraniloyl)-L-alanine	ChEBI
(2S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoate	Generator
3-(2-Amino-3-hydroxybenzoyl)-L-alanine	HMDB
3-Hydroxy-L-kynurenine	HMDB
L-3-HK	HMDB

Molecular Formula

C₁₀H₁₂N₂O₄

Average Mass

224.2133

Monoisotopic Mass

224.079706882

IUPAC Name

(2S)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid

Traditional Name

3-hydroxy-L-kynurenine

CAS Registry Number

606-14-4

SMILES

N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(O)=O

InChI Identifier

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

InChI Key

VCKPUUFAIGNJHC-LURJTMIESA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
L-alpha-amino acid
Alpha-amino acid
Alpha-amino acid or derivatives
O-aminophenol
Gamma-keto acid
Aminophenol
Aniline or substituted anilines
Aryl alkyl ketone
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Keto acid
Beta-aminoketone
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Amino acid or derivatives
Amino acid
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

3-hydroxykynurenine (CHEBI:17380 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.33 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-2.2	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	0.99	ChemAxon
pKa (Strongest Basic)	8.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.03 m³·mol⁻¹	ChemAxon
Polarizability	21.67 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191994	Kynureninase	Unknown	Q16719	Homo sapiens
MMDBp0192045	Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Enzyme	Q8N5Z0	Homo sapiens
MMDBp0192123	Kynurenine--oxoglutarate transaminase 1	Enzyme	Q16773	Homo sapiens
MMDBp0193603	Kynurenine 3-monooxygenase	Unknown	O15229	Homo sapiens
MMDBp0195726	Kynurenine--oxoglutarate transaminase 3	Enzyme	Q6YP21	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019601	L-3-Hydroxykynurenine	L-Alanine	Kynureninase	Cleavage of kynurenine	PathBank	31602464
MMDBr0019602	L-Kynurenine	L-3-Hydroxykynurenine	Kynurenine 3-monooxygenase	Oxygenation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	25	Human feces; Human saliva	Unknown
Bacteria/Eubacteria	Proteobacteria	38	Human feces; Human sputum; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	40	Human ; Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	7	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Firmicutes	2	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	6	Human feces	Metabolic reconstruction
Bacteria	Proteobacteria	1	Human feces; Human sputum; Human ; Human subgingival plaque	Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	3
Bacteria/Eubacteria	Deinococcus-thermus	1
Bacteria/Eubacteria	Acidobacteria	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human Blood	Detected and Quantified	0.0984			uM	Infant (0-1 year old)	Female	Nicotinamide Adenine Dinucleotide Deficiency	HMDB	28792876
Human Urine	Detected and Quantified	2.2	1.0	3.4	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0011631

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

3-HYDROXY-L-KYNURENINE

BiGG ID

Not Available

Wikipedia Link

3-Hydroxykynurenine

METLIN ID

Not Available

PubChem Compound

11811

PDB ID

3DJ

ChEBI ID

17380

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sardar AM, Bell JE, Reynolds GP: Increased concentrations of the neurotoxin 3-hydroxykynurenine in the frontal cortex of HIV-1-positive patients. J Neurochem. 1995 Feb;64(2):932-5. doi: 10.1046/j.1471-4159.1995.64020932.x. [PubMed:7830088 ]
Guidetti P, Schwarcz R: 3-Hydroxykynurenine potentiates quinolinate but not NMDA toxicity in the rat striatum. Eur J Neurosci. 1999 Nov;11(11):3857-63. doi: 10.1046/j.1460-9568.1999.00806.x. [PubMed:10583474 ]

Showing metabocard for L-3-Hydroxykynurenine (MMDBc0032921)

MOL for #<Metabolite:0x00007f91e67d6840>

3D MOL for #<Metabolite:0x00007f91e67d6840>

3D SDF for #<Metabolite:0x00007f91e67d6840>

3D-SDF for #<Metabolite:0x00007f91e67d6840>

PDB for #<Metabolite:0x00007f91e67d6840>

3D PDB for #<Metabolite:0x00007f91e67d6840>

SMILES for #<Metabolite:0x00007f91e67d6840>

INCHI for #<Metabolite:0x00007f91e67d6840>

Structure for #<Metabolite:0x00007f91e67d6840>

3D Structure for #<Metabolite:0x00007f91e67d6840>