MiMeDB: Showing metabocard for L-Kynurenine (MMDBc0032971)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:29:24 UTC

Update Date

2024-04-30 19:56:59 UTC

Metabolite ID

MMDBc0032971

Metabolite Identification

Common Name

L-Kynurenine

Description

L-Kynurenine, which is also known as Kynurenine or 3-Anthraniloylalanine, belongs to the class of compounds known as alkyl-phenylketones. Alkyl-phenylketones are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Kynurenine is a metabolite of the amino acid L-tryptophan and is used in the production of niacin. Specifically, kynurenine is synthesized by the enzyme tryptophan dioxygenase, which is made primarily but not exclusively in the liver. Kynurenine is also synthesized by indoleamine 2,3-dioxygenase (IDO), which is found in many tissues and is often overexpressed in response to immune activation. Kynurenine and its other tryptophan breakdown products (Trp catabolites) carry out a wide range of biological functions, including dilating blood vessels during inflammation (PMID: 20190767 ) and regulating the immune response (PMID: 21041655 ). Kynurenine is the precursor to the neuroprotective agent known as kynurenic acid. Kynurenine is also the precursor to the neurotoxic agent quinolinic acid. Dysregulation in the balance between these two kynurenine derivatives can be observable in many disorders such as stroke, epilepsy, multiple sclerosis, and amyotrophic lateral sclerosis. Blood levels of kynurenine are reduced in people with bipolar disorder (PMID: 33077852 ) and schizophrenia (PMID: 21727251 ). On the other hand, kynurenine production is increased in Alzheimer's disease (PMID: 16008823 ). and cardiovascular disease (PMID: 12814390 ), where its metabolites are associated with cognitive deficits (PMID: 20639188 ) and depressive symptoms. Kynurenine and its precursor (tryptophan) also play important roles in regulating inflammation and the immune responses to infectious organisms. Reduced levels of tryptophan in the blood are typically seen when individuals are fighting chronic infections, suffering from traumatic injuries (burns or wounds) or experiencing sepsis (PMID: 26309411 ). Tryptophan is mainly catabolized to kynurenine by the enzyme known as indoleamine-2,3-dioxygenase (IDO) which is induced by interferon gamma (IFN-gamma or IFNG). Kynurenine activates the aryl hydrocarbon receptor (AhR), which plays a key role immune suppression. The role of IDO is to effectively deplete tryptophan levels to starve infectious organisms (bacteria and parasites), thereby killing them or slowing their growth. On the other hand, the AhR activation by kynurenine leads to a state of immunosuppression and is intended to serve as a brake on the immune response to the infectious organisms (overexpression of IFNG and IL-1B). Unfortunately, tryptophan starvation is often not effective against viruses or even all infectious microbes. As a result, this AhR activation by kynurenine can lead to a situation where viruses (or certain pathogens) continue to survive and multiply even while the immune system is effectively turning off. As a result, high levels of kynurenine and low levels of tryptophan (a high kynurenine to tryptophan or KT ratio) can lead to or even be symptomatic of chronic viral or pathogenic infections or, at worse, sepsis and septic shock (PMID: 33338598 ; PMID: 21731667 ). Kynurenine and its metabolites are also known as uremic toxins (PMID: 12092667 ). Chronically high levels of uremic toxins are known to cause damage to kidneys, liver, heart and the brain. Serum albumin binds to most uremic toxins quite strongly and can act as a first line of defense against transient rises in these compounds.

Structure

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


  Mrv1652305271900182D          

 15 15  0  0  1  0            999 V2000
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032971

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1

> <INCHI_KEY>
YGPSJZOEDVAXAB-QMMMGPOBSA-N

> <FORMULA>
C10H12N2O3

> <MOLECULAR_WEIGHT>
208.2139

> <EXACT_MASS>
208.08479226

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.588301379965444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.93

> <JCHEM_LOGP>
-1.9081918809836254

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.06926978291992

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.193089749657625

> <JCHEM_PKA_STRONGEST_BASIC>
8.96449885088756

> <JCHEM_POLAR_SURFACE_AREA>
106.41

> <JCHEM_REFRACTIVITY>
55.05020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-kynurenine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -6.668   2.310   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0000684
HETATM    1  N1  UNL     1       1.907   2.247   0.936  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.227   0.926   0.493  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.579   0.592   0.412  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.943  -0.661   0.003  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.967  -1.580  -0.325  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.631  -1.234  -0.240  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.238   0.033   0.173  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.165   0.426   0.275  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.394   1.623   0.649  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.297  -0.443  -0.009  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.447  -0.428   0.933  1.00  0.00           C  
HETATM   12  N2  UNL     1      -3.404  -1.427   0.389  1.00  0.00           N  
HETATM   13  C10 UNL     1      -3.204   0.831   1.021  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.736   1.902   1.447  1.00  0.00           O  
HETATM   15  O3  UNL     1      -4.560   0.826   0.598  1.00  0.00           O  
HETATM   16  H1  UNL     1       1.435   2.364   1.849  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.143   3.082   0.350  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.331   1.318   0.670  1.00  0.00           H  
HETATM   19  H4  UNL     1       5.005  -0.920  -0.057  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.245  -2.586  -0.657  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.908  -1.972  -0.503  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.723  -0.099  -1.008  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.011  -1.498  -0.204  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.156  -0.772   1.963  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.192  -1.677  -0.592  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.388  -2.294   0.959  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.882   1.420  -0.126  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3    3    7
CONECT    3    4   18
CONECT    4    5    5   19
CONECT    5    6   20
CONECT    6    7    7   21
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   22   23
CONECT   11   12   13   24
CONECT   12   25   26
CONECT   13   14   14   15
CONECT   15   27
END

Synonyms

Value	Source
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid	ChEBI
3-Anthraniloyl-L-alanine	ChEBI
KYNURENINE	ChEBI
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoate	Generator
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoate	HMDB
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoic acid	HMDB
3-Anthraniloyl-alanine	HMDB
3-Anthraniloylalanine	HMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoate	HMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoic acid	HMDB
DL-Kynurenine	HMDB
Kynurenin	HMDB
Quinurenine	HMDB
L-Kynurenine	HMDB
3-(2-aminobenzoyl)-L-alanine	HMDB
KYNA	HMDB

Molecular Formula

C₁₀H₁₂N₂O₃

Average Mass

208.2139

Monoisotopic Mass

208.08479226

IUPAC Name

(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid

Traditional Name

L-kynurenine

CAS Registry Number

343-65-7

SMILES

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

InChI Identifier

InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1

InChI Key

YGPSJZOEDVAXAB-QMMMGPOBSA-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
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Benzoyl
Gamma-keto acid
Aniline or substituted anilines
Aryl alkyl ketone
Monocyclic benzene moiety
Beta-aminoketone
Keto acid
Benzenoid
Vinylogous amide
Amino acid
Amino acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Primary aliphatic amine
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:16946 )
kynurenine (CHEBI:16946 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.67 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.9	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.19	ChemAxon
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.05 m³·mol⁻¹	ChemAxon
Polarizability	20.59 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014l-0931000000-29fa7c323b035cb399d3	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014l-0931000000-29fa7c323b035cb399d3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014l-0931000000-a43ae0acafac266101c4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-1910000000-fdc25d09b4da4b1d7657	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9500000000-d7bf6a26c74e0dcabf40	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-4920000000-cb575b96b16b3ef9130f	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-2910000000-366ce08b5736d68dfad0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01bd-5900000000-c18e10be7e029474cf03	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kf-9300000000-0f8238d38819f6f30d12	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0a4i-0790000000-3fa45266412288bf1c62	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0007-3900000000-a66f45aff81960af7575	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00xv-5900000000-15442ec5aaef005401ae	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00r7-7900000000-0833fe9d2739d329f197	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9400000000-d5d45364462a730de436	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0006-0900000000-13929f0bde71b6326d3f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0f6w-2900000000-b2d4f361ffee9fd93bb7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-004j-0900000000-96930a886f7bbcc44df3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-2441a358973abdb063da	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0udi-0900000000-dc4fee4751d629575157	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0006-0900000000-4ec06cc06a3eab2625d6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0006-0900000000-319acefac99779fa7552	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0059-0890000000-4280b92b875a6f754a91	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0059-0890000000-664e2c8904363418682e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00dj-0139000000-aa6188977ba2f460f5bc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00dj-0139000000-ee71a364df13bd095feb	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06r7-0920000000-f2e6efdd3988d3010e33	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-022a-3900000000-e1c06099462847ad5b97	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9700000000-a9df2d5ca325f97f69f1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2490000000-9604ae0cc9d437acd878	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-9520000000-8f0ea7d174290496860d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9400000000-9721076505654380d2de	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Brain
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Fibroblasts
Intestine
Liver
Neuron
Placenta
Spleen
Urine

Tissue Locations

Brain
Epidermis
Fibroblasts
Intestine
Liver
Neuron
Placenta
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191954	Aspartate aminotransferase, mitochondrial	Enzyme	P00505	Homo sapiens
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
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo sapiens
MMDBp0193603	Kynurenine 3-monooxygenase	Unknown	O15229	Homo sapiens
MMDBp0193784	Aminoadipate aminotransferase, isoform CRA_b	Enzyme	Q4W5N8	Homo sapiens
MMDBp0194173	Kynurenine formamidase	Unknown	Q63HM1	Homo sapiens
MMDBp0195726	Kynurenine--oxoglutarate transaminase 3	Enzyme	Q6YP21	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Anti-inflammatory pathway
Viral Sepsis

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001216	Water	Formic acid	Not Available		VMH; KEGG	30371894
MMDBr0001532	Water	L-Alanine	Kynureninase		VMH; KEGG	30371894
MMDBr0001533	Hydrogen Ion	Water	Not Available		VMH; KEGG	30371894
MMDBr0001534	Oxoglutaric acid	4-(2-Aminophenyl)-2,4-dioxobutanoic acid	Aminoadipate aminotransferase		VMH	15016471
MMDBr0003964	Oxoglutaric acid	L-Glutamic acid	Cysteine conjugate-beta lyase, cytoplasmic		VMH	10756023
MMDBr0003965	Oxoglutaric acid	L-Glutamic acid	Aminoadipate aminotransferase		VMH	10756023
MMDBr0005567	L-Kynurenine	L-Kynurenine	Solute carrier family 43 (amino acid system l transporter), member 1		VMH	30371894
MMDBr0005568	L-Kynurenine	L-Kynurenine	Solute carrier family 7 (amino acid transporter light chain, l system), member 8		VMH	30371894
MMDBr0005569	L-Leucine	L-Leucine	Solute carrier family 43 (amino acid system l transporter), member 1		VMH	30371894
MMDBr0010405	Hydrogen Ion	3-Hydroxykynurenine-O-Beta-D-Glucoside	Not Available		VMH	30371894
MMDBr0012633	Hydrogen Ion	Hydrogen Ion	Not Available		VMH	30371894
MMDBr0013172	Water	formate	Kynurenine formamidase	Amide hydrolysis	RHEA	34755880
MMDBr0013570	Water	2-Aminobenzoic acid	Kynureninase	Cleavage of kynurenine	RHEA	34755880
MMDBr0014001	Hydrogen Ion	L-3-Hydroxykynurenine	Kynurenine 3-monooxygenase	Oxygenation	RHEA	34755880
MMDBr0017542	alpha-Ketoglutarate	Water	Aromatic amino acid aminotransferase 2	Amine group addition	RHEA	34755880
MMDBr0019602	Hydrogen Ion	NADP	Kynurenine 3-monooxygenase	Oxygenation	PathBank	31602464
MMDBr0019603	Water	Formic acid	Kynurenine formamidase	Amide hydrolysis	PathBank	31602464
MMDBr0019638	Water	L-Alanine	Kynureninase	Cleavage of kynurenine	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Hydrocephalus	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	8583213
Intraventricular hemorrhage	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	8583213
Schizophrenia	Increased	Association	Human Blood	HMDB	25004141
Sepsis	Increased	Association	Human Blood	HMDB	26847922
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	25	Human feces; Human saliva	Unknown
Bacteria	Proteobacteria	95	Human feces; Human sputum; Human ; Turkey ; Human subgingival plaque	Metabolic reconstruction
Bacteria	Firmicutes	68	Human ; Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	8	Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	9	Human feces	Metabolic reconstruction
Bacteria	Deinococcus-thermus	2
Eukaryota/Fungi	Basidiomycota	3
Bacteria	Acidobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	2.6	1.06			uM	Adult (>18 years old)	Not Specified	CNS Infections	HMDB	8583213
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.6	0.58			uM	Adult (>18 years old)	Not Specified	CNS Tumors	HMDB	8583213
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.18	0.040			uM	Adult (>18 years old)	Not Specified	Hydrocephalus	HMDB	8583213
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.25	0.12			uM	Adult (>18 years old)	Not Specified	Intraventricular hemorrhage	HMDB	8583213
Human Blood	Detected and Quantified	1.6				uM	Infant (0-1 year old)	Female	Nicotinamide Adenine Dinucleotide Deficiency	HMDB	28792876
Human Blood	Detected and Quantified	2.35	0.162			uM	Adult (>18 years old)	Both	Schizophrenia	HMDB	25004141
Human Blood	Detected and Quantified	12.5		3.5	27	uM	Adult (>18 years old)	Both	Sepsis	HMDB	26847922
Human Urine	Detected and Quantified			0.256	0.800	umol/mmol creatinine	Children (1-13 years old)	Female	Tryptophanuria with dwarfism	HMDB	14055140
Human Urine	Detected and Quantified	0.41				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0019	0.00021			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	9784247
Human Urine	Detected and Quantified			0.02	0.71	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.052	0.0031			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	1422788
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.054	0.007			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	8583213
Human Urine	Detected and Quantified	0.10		0.02	0.71	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.13		0.02	0.68	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.41		0.08	1.31	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	0.56	0.91			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Urine	Detected and Quantified			0.63	1.6	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.71	0.95	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified	1.345		0.864	1.825	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	14055140
Human Blood	Detected and Quantified	1.4		0.7	3.0	uM	Adult (>18 years old)	Both	Normal	HMDB	8634758
Human Blood	Detected and Quantified	1.6	0.1			uM	Adult (>18 years old)	Both	Normal	HMDB	9784247
Human Urine	Detected and Quantified	1.7		1.1	2.5	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	1.74	0.121			uM	Adult (>18 years old)	Both	Normal	HMDB	25004141
Human Blood	Detected and Quantified	2.21	0.57			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	2.61		2.02	3.16	uM	Children (1-13 uears old)	Both	Normal	HMDB	27294788
Human Blood	Detected and Quantified	4.13		3.44	4.91	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	5.89		4.89	7.05	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Urine	Detected and Quantified	0.7154	0.8277			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	0.7503	0.3831			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	2.4	0.5			uM	Adult (>18 years old)	Male	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 and Quantified	2.85	1.94			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 Blood	Detected and Quantified			1.1	3.2	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Both	Normal	HMDB	27609529
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
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

HMDB0000684

DrugBank ID

DB02070

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

161166

PDB ID

Not Available

ChEBI ID

16946

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Joseph MH: Determination of kynurenine by a simple gas-liquid chromatographic method applicable to urine, plasma, brain and cerebrospinal fluid. J Chromatogr. 1978 Jul 1;146(1):33-41. doi: 10.1016/s0378-4347(00)81287-6. [PubMed:670356 ]
Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [PubMed:1244085 ]
Heyes MP, Saito K, Crowley JS, Davis LE, Demitrack MA, Der M, Dilling LA, Elia J, Kruesi MJ, Lackner A, et al.: Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Brain. 1992 Oct;115 ( Pt 5):1249-73. doi: 10.1093/brain/115.5.1249. [PubMed:1422788 ]
Okuno E, Nakamura M, Schwarcz R: Two kynurenine aminotransferases in human brain. Brain Res. 1991 Mar 1;542(2):307-12. doi: 10.1016/0006-8993(91)91583-m. [PubMed:2029638 ]
Heinmets F: Computer simulation and analysis of tryptophan metabolism via kynurenine pathway in liver. Comput Biol Med. 1974 Sep;1(4):323-36. doi: 10.1016/0010-4825(71)90007-2. [PubMed:4600391 ]
Greengard O: Relationship between urinary excretion of kynurenine and liver tryptophan oxygenase activity. Am J Clin Nutr. 1971 Jun;24(6):709-11. doi: 10.1093/ajcn/24.6.709. [PubMed:5581008 ]
Altman K, Greengard O: Correlation of kynurenine excretion with liver tryptophan pyrrolase levels in disease and after hydrocortisone induction. J Clin Invest. 1966 Oct;45(10):1527-34. doi: 10.1172/JCI105459. [PubMed:5925511 ]
Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. doi: 10.1016/0022-510x(95)00164-w. [PubMed:8583213 ]
Pearson SJ, Meldrum A, Reynolds GP: An investigation of the activities of 3-hydroxykynureninase and kynurenine aminotransferase in the brain in Huntington's disease. J Neural Transm Gen Sect. 1995;102(1):67-73. doi: 10.1007/BF01276566. [PubMed:8785025 ]
Moroni F, Carpenedo R, Chiarugi A: Kynurenine hydroxylase and kynureninase inhibitors as tools to study the role of kynurenine metabolites in the central nervous system. Adv Exp Med Biol. 1996;398:203-10. doi: 10.1007/978-1-4613-0381-7_33. [PubMed:8906267 ]
Heyes MP, Saito K, Lackner A, Wiley CA, Achim CL, Markey SP: Sources of the neurotoxin quinolinic acid in the brain of HIV-1-infected patients and retrovirus-infected macaques. FASEB J. 1998 Jul;12(10):881-96. doi: 10.1096/fasebj.12.10.881. [PubMed:9657528 ]
Fujigaki S, Saito K, Takemura M, Fujii H, Wada H, Noma A, Seishima M: Species differences in L-tryptophan-kynurenine pathway metabolism: quantification of anthranilic acid and its related enzymes. Arch Biochem Biophys. 1998 Oct 15;358(2):329-35. doi: 10.1006/abbi.1998.0861. [PubMed:9784247 ]
Widner B, Sepp N, Kowald E, Kind S, Schmuth M, Fuchs D: Degradation of tryptophan in patients with systemic lupus erythematosus. Adv Exp Med Biol. 1999;467:571-7. doi: 10.1007/978-1-4615-4709-9_71. [PubMed:10721102 ]
Martinsons A, Rudzite V, Groma V, Bratslavska O, Widner B, Fuchs D: Kynurenine and neopterin in chronic glomerulonephritis. Adv Exp Med Biol. 1999;467:579-86. doi: 10.1007/978-1-4615-4709-9_72. [PubMed:10721103 ]
Widner B, Werner ER, Schennach H, Fuchs D: An HPLC method to determine tryptophan and kynurenine in serum simultaneously. Adv Exp Med Biol. 1999;467:827-32. doi: 10.1007/978-1-4615-4709-9_105. [PubMed:10721136 ]
Widner B, Sepp N, Kowald E, Ortner U, Wirleitner B, Fritsch P, Baier-Bitterlich G, Fuchs D: Enhanced tryptophan degradation in systemic lupus erythematosus. Immunobiology. 2000 Apr;201(5):621-30. doi: 10.1016/S0171-2985(00)80079-0. [PubMed:10834318 ]
Saito K, Fujigaki S, Heyes MP, Shibata K, Takemura M, Fujii H, Wada H, Noma A, Seishima M: Mechanism of increases in L-kynurenine and quinolinic acid in renal insufficiency. Am J Physiol Renal Physiol. 2000 Sep;279(3):F565-72. doi: 10.1152/ajprenal.2000.279.3.F565. [PubMed:10966936 ]
Pawlak D, Pawlak K, Malyszko J, Mysliwiec M, Buczko W: Accumulation of toxic products degradation of kynurenine in hemodialyzed patients. Int Urol Nephrol. 2001;33(2):399-404. doi: 10.1023/a:1015238418500. [PubMed:12092667 ]
Wirleitner B, Rudzite V, Neurauter G, Murr C, Kalnins U, Erglis A, Trusinskis K, Fuchs D: Immune activation and degradation of tryptophan in coronary heart disease. Eur J Clin Invest. 2003 Jul;33(7):550-4. doi: 10.1046/j.1365-2362.2003.01186.x. [PubMed:12814390 ]
Medana IM, Day NP, Salahifar-Sabet H, Stocker R, Smythe G, Bwanaisa L, Njobvu A, Kayira K, Turner GD, Taylor TE, Hunt NH: Metabolites of the kynurenine pathway of tryptophan metabolism in the cerebrospinal fluid of Malawian children with malaria. J Infect Dis. 2003 Sep 15;188(6):844-9. doi: 10.1086/377583. Epub 2003 Sep 9. [PubMed:12964115 ]
Manuelpillai U, Nicholls T, Wallace EM, Phillips DJ, Guillemin G, Walker D: Increased mRNA expression of kynurenine pathway enzymes in human placentae exposed to bacterial endotoxin. Adv Exp Med Biol. 2003;527:85-9. doi: 10.1007/978-1-4615-0135-0_9. [PubMed:15206719 ]
Guillemin GJ, Brew BJ, Noonan CE, Takikawa O, Cullen KM: Indoleamine 2,3 dioxygenase and quinolinic acid immunoreactivity in Alzheimer's disease hippocampus. Neuropathol Appl Neurobiol. 2005 Aug;31(4):395-404. doi: 10.1111/j.1365-2990.2005.00655.x. [PubMed:16008823 ]
Hartai Z, Klivenyi P, Janaky T, Penke B, Dux L, Vecsei L: Kynurenine metabolism in plasma and in red blood cells in Parkinson's disease. J Neurol Sci. 2005 Dec 15;239(1):31-5. doi: 10.1016/j.jns.2005.07.006. Epub 2005 Aug 15. [PubMed:16099471 ]
Wang Y, Liu H, McKenzie G, Witting PK, Stasch JP, Hahn M, Changsirivathanathamrong D, Wu BJ, Ball HJ, Thomas SR, Kapoor V, Celermajer DS, Mellor AL, Keaney JF Jr, Hunt NH, Stocker R: Kynurenine is an endothelium-derived relaxing factor produced during inflammation. Nat Med. 2010 Mar;16(3):279-85. doi: 10.1038/nm.2092. Epub 2010 Feb 28. [PubMed:20190767 ]
Gulaj E, Pawlak K, Bien B, Pawlak D: Kynurenine and its metabolites in Alzheimer's disease patients. Adv Med Sci. 2010;55(2):204-11. doi: 10.2478/v10039-010-0023-6. [PubMed:20639188 ]
Nguyen NT, Kimura A, Nakahama T, Chinen I, Masuda K, Nohara K, Fujii-Kuriyama Y, Kishimoto T: Aryl hydrocarbon receptor negatively regulates dendritic cell immunogenicity via a kynurenine-dependent mechanism. Proc Natl Acad Sci U S A. 2010 Nov 16;107(46):19961-6. doi: 10.1073/pnas.1014465107. Epub 2010 Nov 1. [PubMed:21041655 ]
Wonodi I, Stine OC, Sathyasaikumar KV, Roberts RC, Mitchell BD, Hong LE, Kajii Y, Thaker GK, Schwarcz R: Downregulated kynurenine 3-monooxygenase gene expression and enzyme activity in schizophrenia and genetic association with schizophrenia endophenotypes. Arch Gen Psychiatry. 2011 Jul;68(7):665-74. doi: 10.1001/archgenpsychiatry.2011.71. [PubMed:21727251 ]
Darcy CJ, Davis JS, Woodberry T, McNeil YR, Stephens DP, Yeo TW, Anstey NM: An observational cohort study of the kynurenine to tryptophan ratio in sepsis: association with impaired immune and microvascular function. PLoS One. 2011;6(6):e21185. doi: 10.1371/journal.pone.0021185. Epub 2011 Jun 22. [PubMed:21731667 ]
Mehraj V, Routy JP: Tryptophan Catabolism in Chronic Viral Infections: Handling Uninvited Guests. Int J Tryptophan Res. 2015 Aug 4;8:41-8. doi: 10.4137/IJTR.S26862. eCollection 2015. [PubMed:26309411 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Bartoli F, Misiak B, Callovini T, Cavaleri D, Cioni RM, Crocamo C, Savitz JB, Carra G: The kynurenine pathway in bipolar disorder: a meta-analysis on the peripheral blood levels of tryptophan and related metabolites. Mol Psychiatry. 2021 Jul;26(7):3419-3429. doi: 10.1038/s41380-020-00913-1. Epub 2020 Oct 19. [PubMed:33077852 ]
Lionetto L, Ulivieri M, Capi M, De Bernardini D, Fazio F, Petrucca A, Pomes LM, De Luca O, Gentile G, Casolla B, Curto M, Salerno G, Schillizzi S, Torre MS, Santino I, Rocco M, Marchetti P, Aceti A, Ricci A, Bonfini R, Nicoletti F, Simmaco M, Borro M: Increased kynurenine-to-tryptophan ratio in the serum of patients infected with SARS-CoV2: An observational cohort study. Biochim Biophys Acta Mol Basis Dis. 2021 Mar 1;1867(3):166042. doi: 10.1016/j.bbadis.2020.166042. Epub 2020 Dec 16. [PubMed:33338598 ]

Showing metabocard for L-Kynurenine (MMDBc0032971)

MOL for #<Metabolite:0x000055e8c5d85640>

3D MOL for #<Metabolite:0x000055e8c5d85640>

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3D-SDF for #<Metabolite:0x000055e8c5d85640>

PDB for #<Metabolite:0x000055e8c5d85640>

3D PDB for #<Metabolite:0x000055e8c5d85640>

SMILES for #<Metabolite:0x000055e8c5d85640>

INCHI for #<Metabolite:0x000055e8c5d85640>

Structure for #<Metabolite:0x000055e8c5d85640>

3D Structure for #<Metabolite:0x000055e8c5d85640>