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

Human

Record Information

Version

2.0

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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-057u-7910000000-88ad37433d9fe2009b5e	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0596-8379000000-0b0a9595aae2502a55ac	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0960000000-c33d63911a63b0e55059	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0209-2900000000-733debea97f59a15a620	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-6900000000-908957a56bc62255065a	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1290000000-49db02e2f97330c6041f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9650000000-45bd0384724255104d6c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-7900000000-e62c0de8b7c63b9e4066	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0890000000-24d8093dfa7cd7471959	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-070i-1900000000-3159845d0fd09fc5476c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9700000000-c823da7e7ec85255fba0	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-0690000000-e55cff3d90188bbe1b4f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1910000000-15ef15dcef2ce9fdfef5	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-6900000000-2b99b24490fd7fc7a3f9	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	456.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	221.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	82.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	293.1
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	271.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	254.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	751.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	701.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	608.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	147.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	439.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	163.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	69.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	340.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	479.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	68.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	210.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	820.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	622.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	L-3-Hydroxykynurenine_TMS_1	C[Si](C)(C)OC1=CC=CC(C(=O)C[C@H](N)C(=O)O)=C1N	standard non polar	2025-10-24	2140.56
Gas Chromatography	L-3-Hydroxykynurenine_TMS_2	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC(O)=C1N	standard non polar	2025-10-24	2353.14
Gas Chromatography	L-3-Hydroxykynurenine_TMS_3	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(=O)O	standard non polar	2025-10-24	1788.58
Gas Chromatography	L-3-Hydroxykynurenine_TMS_4	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@H](N)C(=O)O	standard non polar	2025-10-24	1900.61
Gas Chromatography	L-3-Hydroxykynurenine_TMS_5	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N	standard non polar	2025-10-24	2474.81
Gas Chromatography	L-3-Hydroxykynurenine_TMS_6	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N)C(=O)O	standard non polar	2025-10-24	2137.16
Gas Chromatography	L-3-Hydroxykynurenine_TMS_7	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@H](N)C(=O)O	standard non polar	2025-10-24	1805.26
Gas Chromatography	L-3-Hydroxykynurenine_TMS_8	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1475.58
Gas Chromatography	L-3-Hydroxykynurenine_TMS_9	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1855.36
Gas Chromatography	L-3-Hydroxykynurenine_TMS_10	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	2011.71
Gas Chromatography	L-3-Hydroxykynurenine_TMS_11	C[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC(O)=C1N)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2033.64
Gas Chromatography	L-3-Hydroxykynurenine_TMS_12	C[Si](C)(C)N(C1=C(O)C=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1958.23
Gas Chromatography	L-3-Hydroxykynurenine_TMS_13	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1391.94
Gas Chromatography	L-3-Hydroxykynurenine_TMS_14	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1837.84
Gas Chromatography	L-3-Hydroxykynurenine_TMS_15	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1321.24
Gas Chromatography	L-3-Hydroxykynurenine_TMS_16	C[Si](C)(C)OC1=CC=CC(C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1N	standard non polar	2025-10-24	2188.73
Gas Chromatography	L-3-Hydroxykynurenine_TMS_17	C[Si](C)(C)OC1=CC=CC(C(=O)C[C@H](N)C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1900.73
Gas Chromatography	L-3-Hydroxykynurenine_TMS_18	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1982.18
Gas Chromatography	L-3-Hydroxykynurenine_TMS_19	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC(O)=C1N)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1734.98
Gas Chromatography	L-3-Hydroxykynurenine_TMS_20	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1494.02
Gas Chromatography	L-3-Hydroxykynurenine_TMS_21	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	2712.51
Gas Chromatography	L-3-Hydroxykynurenine_TMS_22	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2131.53
Gas Chromatography	L-3-Hydroxykynurenine_TMS_23	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1309.86
Gas Chromatography	L-3-Hydroxykynurenine_TMS_24	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1901.66
Gas Chromatography	L-3-Hydroxykynurenine_TMS_25	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2473.22
Gas Chromatography	L-3-Hydroxykynurenine_TMS_26	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1722.61
Gas Chromatography	L-3-Hydroxykynurenine_TMS_27	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1735.34
Gas Chromatography	L-3-Hydroxykynurenine_TMS_28	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2307.24
Gas Chromatography	L-3-Hydroxykynurenine_TMS_29	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2504.54
Gas Chromatography	L-3-Hydroxykynurenine_TMS_30	C[Si](C)(C)N(C1=C(O)C=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2747.91
Gas Chromatography	L-3-Hydroxykynurenine_TMS_31	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2277.33
Gas Chromatography	L-3-Hydroxykynurenine_TMS_32	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1969.06
Gas Chromatography	L-3-Hydroxykynurenine_TMS_33	C[Si](C)(C)OC1=CC=CC(C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2167.51
Gas Chromatography	L-3-Hydroxykynurenine_TMS_34	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2507.49
Gas Chromatography	L-3-Hydroxykynurenine_TMS_35	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1768.81
Gas Chromatography	L-3-Hydroxykynurenine_TMS_1	C[Si](C)(C)OC1=CC=CC(C(=O)C[C@H](N)C(=O)O)=C1N	standard polar	2025-10-24	1639.58
Gas Chromatography	L-3-Hydroxykynurenine_TMS_2	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC(O)=C1N	standard polar	2025-10-24	2155.3
Gas Chromatography	L-3-Hydroxykynurenine_TMS_3	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(=O)O	standard polar	2025-10-24	2000.92
Gas Chromatography	L-3-Hydroxykynurenine_TMS_4	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@H](N)C(=O)O	standard polar	2025-10-24	1605.07
Gas Chromatography	L-3-Hydroxykynurenine_TMS_5	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N	standard polar	2025-10-24	1816.62
Gas Chromatography	L-3-Hydroxykynurenine_TMS_6	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N)C(=O)O	standard polar	2025-10-24	2373.76
Gas Chromatography	L-3-Hydroxykynurenine_TMS_7	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@H](N)C(=O)O	standard polar	2025-10-24	1546.59
Gas Chromatography	L-3-Hydroxykynurenine_TMS_8	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2521.62
Gas Chromatography	L-3-Hydroxykynurenine_TMS_9	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1316.42
Gas Chromatography	L-3-Hydroxykynurenine_TMS_10	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2093.2
Gas Chromatography	L-3-Hydroxykynurenine_TMS_11	C[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC(O)=C1N)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2493.09
Gas Chromatography	L-3-Hydroxykynurenine_TMS_12	C[Si](C)(C)N(C1=C(O)C=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2066.87
Gas Chromatography	L-3-Hydroxykynurenine_TMS_13	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2432.89
Gas Chromatography	L-3-Hydroxykynurenine_TMS_14	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1914.73
Gas Chromatography	L-3-Hydroxykynurenine_TMS_15	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	1553.4
Gas Chromatography	L-3-Hydroxykynurenine_TMS_16	C[Si](C)(C)OC1=CC=CC(C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1N	standard polar	2025-10-24	2273.12
Gas Chromatography	L-3-Hydroxykynurenine_TMS_17	C[Si](C)(C)OC1=CC=CC(C(=O)C[C@H](N)C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1829.66
Gas Chromatography	L-3-Hydroxykynurenine_TMS_18	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1390.06
Gas Chromatography	L-3-Hydroxykynurenine_TMS_19	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC(O)=C1N)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2238.09
Gas Chromatography	L-3-Hydroxykynurenine_TMS_20	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2263.49
Gas Chromatography	L-3-Hydroxykynurenine_TMS_21	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2417.12
Gas Chromatography	L-3-Hydroxykynurenine_TMS_22	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2045.12
Gas Chromatography	L-3-Hydroxykynurenine_TMS_23	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1912.52
Gas Chromatography	L-3-Hydroxykynurenine_TMS_24	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2430.58
Gas Chromatography	L-3-Hydroxykynurenine_TMS_25	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1606.58
Gas Chromatography	L-3-Hydroxykynurenine_TMS_26	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	1907.49
Gas Chromatography	L-3-Hydroxykynurenine_TMS_27	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1083.05
Gas Chromatography	L-3-Hydroxykynurenine_TMS_28	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1452.62
Gas Chromatography	L-3-Hydroxykynurenine_TMS_29	C[Si](C)(C)NC1=C(O)C=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1834.88
Gas Chromatography	L-3-Hydroxykynurenine_TMS_30	C[Si](C)(C)N(C1=C(O)C=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2809.29
Gas Chromatography	L-3-Hydroxykynurenine_TMS_31	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1944.75
Gas Chromatography	L-3-Hydroxykynurenine_TMS_32	C[Si](C)(C)NC1=C(O[Si](C)(C)C)C=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2344.49
Gas Chromatography	L-3-Hydroxykynurenine_TMS_33	C[Si](C)(C)OC1=CC=CC(C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1583.99
Gas Chromatography	L-3-Hydroxykynurenine_TMS_34	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC(O)=C1N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1715.93
Gas Chromatography	L-3-Hydroxykynurenine_TMS_35	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC(O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2285.24

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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	39	Human feces; Human sputum; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	42	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	8	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	6	Human feces	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

CMMC Knowledgebase

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:0x00007f2e28016c30>

3D MOL for #<Metabolite:0x00007f2e28016c30>

3D SDF for #<Metabolite:0x00007f2e28016c30>

3D-SDF for #<Metabolite:0x00007f2e28016c30>

PDB for #<Metabolite:0x00007f2e28016c30>

3D PDB for #<Metabolite:0x00007f2e28016c30>

SMILES for #<Metabolite:0x00007f2e28016c30>

INCHI for #<Metabolite:0x00007f2e28016c30>

Structure for #<Metabolite:0x00007f2e28016c30>

3D Structure for #<Metabolite:0x00007f2e28016c30>