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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-07-07 20:53:57 UTC

HMDB ID

HMDB0000684

Secondary Accession Numbers

HMDB0000183
HMDB00183
HMDB00684

Metabolite Identification

Common Name

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>
HMDB0000684

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₁₀H₁₂N₂O₃

Average Molecular Weight

208.2139

Monoisotopic Molecular Weight

208.08479226

IUPAC Name

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

Traditional Name

L-kynurenine

CAS Registry Number

2922-83-0

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 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Cns tumor (HMDB: HMDB0000684)
Cns infection (HMDB: HMDB0000684)
Intraventricular hemorrhage (HMDB: HMDB0000684)
Hydrocephalus (HMDB: HMDB0000684)

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000684)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8634758)
Cerebrospinal Fluid (CSF) (PMID: 1422788)
Cerebrospinal fluid (HMDB: HMDB0000684)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000684)

Organ

Tissue

Epithelium

Epidermis (HMDB: HMDB0000684)

Excreta

Biofluid or Excreta

Urine (PMID: 2026685)
Feces (PMID: 27609529)

Cellular substructure

Cytoplasm (HMDB: HMDB0000684)

Organelle

Mitochondrion (HMDB: HMDB0000684)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000684)

Source

Exogenous

Exogenous (HMDB: HMDB0000684)

Food

Food (HMDB: HMDB0000684)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Endogenous

Endogenous (HMDB: HMDB0000684)

Animal

Animal (HMDB: HMDB0000684)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0000684)
NAD Metabolism (PathBank: SMP0002338)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000684)

Biomarker

Schizophrenia (MarkerDB: MDB00029988)
Hydrocephalus (MarkerDB: MDB00029988)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	191 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	149.059	30932474
[M+H]+	Not Available	149.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000515

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	148.699	31661259
DarkChem	[M-H]-	146.271	31661259
AllCCS	[M+H]+	146.937	32859911
AllCCS	[M-H]-	144.926	32859911
DeepCCS	[M+H]+	144.259	30932474
DeepCCS	[M-H]-	141.864	30932474
DeepCCS	[M-2H]-	175.569	30932474
DeepCCS	[M+Na]+	150.262	30932474
AllCCS	[M+H]+	146.9	32859911
AllCCS	[M+H-H2O]+	143.0	32859911
AllCCS	[M+NH4]+	150.6	32859911
AllCCS	[M+Na]+	151.7	32859911
AllCCS	[M-H]-	144.9	32859911
AllCCS	[M+Na-2H]-	145.4	32859911
AllCCS	[M+HCOO]-	146.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Kynurenine	N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O	3267.7	Standard polar	33892256
L-Kynurenine	N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O	1988.3	Standard non polar	33892256
L-Kynurenine	N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O	2180.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Kynurenine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N	2063.8	Semi standard non polar	33892256
L-Kynurenine,1TMS,isomer #2	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O	2111.3	Semi standard non polar	33892256
L-Kynurenine,1TMS,isomer #3	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O	2162.4	Semi standard non polar	33892256
L-Kynurenine,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C	2096.5	Semi standard non polar	33892256
L-Kynurenine,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C	2129.6	Standard non polar	33892256
L-Kynurenine,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C	2993.1	Standard polar	33892256
L-Kynurenine,2TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C	2135.3	Semi standard non polar	33892256
L-Kynurenine,2TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C	2180.7	Standard non polar	33892256
L-Kynurenine,2TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C	2878.8	Standard polar	33892256
L-Kynurenine,2TMS,isomer #3	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O	2191.3	Semi standard non polar	33892256
L-Kynurenine,2TMS,isomer #3	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O	2195.0	Standard non polar	33892256
L-Kynurenine,2TMS,isomer #3	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O	2855.4	Standard polar	33892256
L-Kynurenine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C	2207.2	Semi standard non polar	33892256
L-Kynurenine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C	2264.8	Standard non polar	33892256
L-Kynurenine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C	3148.5	Standard polar	33892256
L-Kynurenine,2TMS,isomer #5	C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C	2124.7	Semi standard non polar	33892256
L-Kynurenine,2TMS,isomer #5	C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C	2284.3	Standard non polar	33892256
L-Kynurenine,2TMS,isomer #5	C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C	3147.7	Standard polar	33892256
L-Kynurenine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2195.7	Semi standard non polar	33892256
L-Kynurenine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2192.8	Standard non polar	33892256
L-Kynurenine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2572.7	Standard polar	33892256
L-Kynurenine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C)[Si](C)(C)C	2247.5	Semi standard non polar	33892256
L-Kynurenine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C)[Si](C)(C)C	2262.4	Standard non polar	33892256
L-Kynurenine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C)[Si](C)(C)C	2889.3	Standard polar	33892256
L-Kynurenine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2105.8	Semi standard non polar	33892256
L-Kynurenine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2289.6	Standard non polar	33892256
L-Kynurenine,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2673.6	Standard polar	33892256
L-Kynurenine,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2156.4	Semi standard non polar	33892256
L-Kynurenine,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2300.8	Standard non polar	33892256
L-Kynurenine,3TMS,isomer #4	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2646.9	Standard polar	33892256
L-Kynurenine,3TMS,isomer #5	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2307.0	Semi standard non polar	33892256
L-Kynurenine,3TMS,isomer #5	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2318.0	Standard non polar	33892256
L-Kynurenine,3TMS,isomer #5	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2707.2	Standard polar	33892256
L-Kynurenine,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2189.6	Semi standard non polar	33892256
L-Kynurenine,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2286.1	Standard non polar	33892256
L-Kynurenine,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2395.1	Standard polar	33892256
L-Kynurenine,4TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2377.8	Semi standard non polar	33892256
L-Kynurenine,4TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2312.8	Standard non polar	33892256
L-Kynurenine,4TMS,isomer #2	C[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2514.6	Standard polar	33892256
L-Kynurenine,4TMS,isomer #3	C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2332.8	Semi standard non polar	33892256
L-Kynurenine,4TMS,isomer #3	C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2423.3	Standard non polar	33892256
L-Kynurenine,4TMS,isomer #3	C[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2507.8	Standard polar	33892256
L-Kynurenine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2408.2	Semi standard non polar	33892256
L-Kynurenine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2406.6	Standard non polar	33892256
L-Kynurenine,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2335.5	Standard polar	33892256
L-Kynurenine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N	2334.7	Semi standard non polar	33892256
L-Kynurenine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O	2350.9	Semi standard non polar	33892256
L-Kynurenine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O	2406.2	Semi standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C(C)(C)C	2574.2	Semi standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C(C)(C)C	2586.3	Standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O[Si](C)(C)C(C)(C)C	3063.7	Standard polar	33892256
L-Kynurenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2599.4	Semi standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2659.4	Standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	3001.3	Standard polar	33892256
L-Kynurenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2651.6	Semi standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2645.1	Standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2993.1	Standard polar	33892256
L-Kynurenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C(C)(C)C	2703.7	Semi standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C(C)(C)C	2684.5	Standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC(=O)C1=CC=CC=C1N)C(=O)O)[Si](C)(C)C(C)(C)C	3130.1	Standard polar	33892256
L-Kynurenine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2613.2	Semi standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2665.1	Standard non polar	33892256
L-Kynurenine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	3142.6	Standard polar	33892256
L-Kynurenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2840.4	Semi standard non polar	33892256
L-Kynurenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2826.9	Standard non polar	33892256
L-Kynurenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2896.3	Standard polar	33892256
L-Kynurenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2913.4	Semi standard non polar	33892256
L-Kynurenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2889.5	Standard non polar	33892256
L-Kynurenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3042.5	Standard polar	33892256
L-Kynurenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2774.4	Semi standard non polar	33892256
L-Kynurenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2879.0	Standard non polar	33892256
L-Kynurenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2919.4	Standard polar	33892256
L-Kynurenine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2831.6	Semi standard non polar	33892256
L-Kynurenine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2875.4	Standard non polar	33892256
L-Kynurenine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2916.0	Standard polar	33892256
L-Kynurenine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3000.2	Semi standard non polar	33892256
L-Kynurenine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2899.7	Standard non polar	33892256
L-Kynurenine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2960.0	Standard polar	33892256
L-Kynurenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3011.5	Semi standard non polar	33892256
L-Kynurenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3022.1	Standard non polar	33892256
L-Kynurenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2816.4	Standard polar	33892256
L-Kynurenine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3208.3	Semi standard non polar	33892256
L-Kynurenine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3061.9	Standard non polar	33892256
L-Kynurenine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)C[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2902.5	Standard polar	33892256
L-Kynurenine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3215.5	Semi standard non polar	33892256
L-Kynurenine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3119.2	Standard non polar	33892256
L-Kynurenine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2846.8	Standard polar	33892256
L-Kynurenine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3431.7	Semi standard non polar	33892256
L-Kynurenine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3265.5	Standard non polar	33892256
L-Kynurenine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2816.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Kynurenine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014l-0931000000-29fa7c323b035cb399d3	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kynurenine GC-EI-TOF (Non-derivatized)	splash10-014l-0931000000-29fa7c323b035cb399d3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kynurenine GC-EI-TOF (Non-derivatized)	splash10-014l-0931000000-a43ae0acafac266101c4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kynurenine GC-EI-TOF (Non-derivatized)	splash10-0006-1910000000-fdc25d09b4da4b1d7657	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9500000000-d7bf6a26c74e0dcabf40	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-4920000000-cb575b96b16b3ef9130f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kynurenine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0006-2910000000-366ce08b5736d68dfad0	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-01bd-5900000000-c18e10be7e029474cf03	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00kf-9300000000-0f8238d38819f6f30d12	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0a4i-0790000000-3fa45266412288bf1c62	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-0007-3900000000-a66f45aff81960af7575	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-00xv-5900000000-15442ec5aaef005401ae	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-00r7-7900000000-0833fe9d2739d329f197	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-0006-9400000000-d5d45364462a730de436	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0006-0900000000-13929f0bde71b6326d3f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0f6w-2900000000-b2d4f361ffee9fd93bb7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-004j-0900000000-96930a886f7bbcc44df3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-000i-0900000000-2441a358973abdb063da	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0udi-0900000000-dc4fee4751d629575157	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOF	splash10-0006-0900000000-4ec06cc06a3eab2625d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOF	splash10-0006-0900000000-319acefac99779fa7552	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOF	splash10-0059-0890000000-4280b92b875a6f754a91	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOF	splash10-0059-0890000000-664e2c8904363418682e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOF	splash10-00dj-0139000000-aa6188977ba2f460f5bc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kynurenine Linear Ion Trap , negative-QTOF	splash10-00dj-0139000000-ee71a364df13bd095feb	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenine 10V, Positive-QTOF	splash10-06r7-0920000000-f2e6efdd3988d3010e33	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenine 20V, Positive-QTOF	splash10-022a-3900000000-e1c06099462847ad5b97	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenine 40V, Positive-QTOF	splash10-00di-9700000000-a9df2d5ca325f97f69f1	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenine 10V, Negative-QTOF	splash10-0a4i-2490000000-9604ae0cc9d437acd878	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenine 20V, Negative-QTOF	splash10-00dl-9520000000-8f0ea7d174290496860d	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kynurenine 40V, Negative-QTOF	splash10-006x-9400000000-9721076505654380d2de	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Brain
Epidermis
Fibroblasts
Intestine
Liver
Neuron
Placenta
Spleen

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.6 +/- 0.1 uM	Adult (>18 years old)	Both	Normal	9784247	details
Blood	Detected and Quantified	1.4 (0.7-3.0) uM	Adult (>18 years old)	Both	Normal	8634758	details
Blood	Detected and Quantified	5.89 (4.89-7.05) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	2.4 +/- 0.5 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	1.74 +/- 0.121 uM	Adult (>18 years old)	Both	Normal	25004141	details
Blood	Detected and Quantified	4.13 (3.44-4.91) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	2.21 +/- 0.57 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	2.61(2.02-3.16) uM	Children (1-13 uears old)	Both	Normal	27294788	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	1.1-3.2 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0019 +/- 0.00021 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9784247	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.052 +/- 0.0031 uM	Adult (>18 years old)	Not Specified	Normal	1422788	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.054 +/- 0.007 uM	Adult (>18 years old)	Not Specified	Normal	8583213	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Urine	Detected and Quantified	0.7503 +/- 0.3831 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.41 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected and Quantified	2.85 +/- 1.94 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.02-0.71 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.13(0.02-0.68) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.10(0.02-0.71) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	1.345 (0.864-1.825) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	14055140	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.63-1.6 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	0.18 (0.08-0.70) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	1.7 (1.1-2.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.41 (0.08-1.31) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.71-0.95 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	0.56 +/- 0.91 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	12.5(3.5-27) uM	Adult (>18 years old)	Both	Sepsis	26847922	details
Blood	Detected and Quantified	2.35 +/- 0.162 uM	Adult (>18 years old)	Both	Schizophrenia	25004141	details
Blood	Detected and Quantified	2.82(2.09-3.58) uM	Children (1-13 uears old)	Both	Environmental enteric dysfunction	27294788	details
Blood	Detected and Quantified	1.6 uM	Infant (0-1 year old)	Female	Nicotinamide Adenine Dinucleotide Deficiency	28792876	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.18 +/- 0.040 uM	Adult (>18 years old)	Not Specified	Hydrocephalus	8583213	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.25 +/- 0.12 uM	Adult (>18 years old)	Not Specified	Intraventricular hemorrhage	8583213	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.6 +/- 0.58 uM	Adult (>18 years old)	Not Specified	CNS Tumors	8583213	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.6 +/- 1.06 uM	Adult (>18 years old)	Not Specified	CNS Infections	8583213	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Enthesitis-related arthritis	27786174	details
Urine	Detected and Quantified	0.7154 +/- 0.8277 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.6012 +/- 0.6597 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	0.256-0.800 umol/mmol creatinine	Children (1-13 years old)	Female	Tryptophanuria with dwarfism	14055140	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
Nicotinamide Adenine Dinucleotide Deficiency
Shi H, Enriquez A, Rapadas M, Martin EMMA, Wang R, Moreau J, Lim CK, Szot JO, Ip E, Hughes JN, Sugimoto K, Humphreys DT, McInerney-Leo AM, Leo PJ, Maghzal GJ, Halliday J, Smith J, Colley A, Mark PR, Collins F, Sillence DO, Winlaw DS, Ho JWK, Guillemin GJ, Brown MA, Kikuchi K, Thomas PQ, Stocker R, Giannoulatou E, Chapman G, Duncan EL, Sparrow DB, Dunwoodie SL: NAD Deficiency, Congenital Malformations, and Niacin Supplementation. N Engl J Med. 2017 Aug 10;377(6):544-552. doi: 10.1056/NEJMoa1616361. [PubMed:28792876 ]
Sepsis
Ferrario M, Cambiaghi A, Brunelli L, Giordano S, Caironi P, Guatteri L, Raimondi F, Gattinoni L, Latini R, Masson S, Ristagno G, Pastorelli R: Mortality prediction in patients with severe septic shock: a pilot study using a target metabolomics approach. Sci Rep. 2016 Feb 5;6:20391. doi: 10.1038/srep20391. [PubMed:26847922 ]
Hydrocephalus
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. [PubMed:8583213 ]
Intraventricular hemorrhage
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. [PubMed:8583213 ]
CNS tumors
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. [PubMed:8583213 ]
CNS infections
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. [PubMed:8583213 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Tryptophanuria with dwarfism
TADA K, ITO H, WADA Y, ARAKAWA T: CONGENITAL TRYPTOPHANURIA WITH DWARFISM ("H" DISEASE-LIKE CLINICAL FEATURES WITHOUT INDICANURIA AND GENERALIZED AMINOACIDURIA):--A PROBABLY NEW INBORN ERROR OF TRYPTOPHAN METABOLISM. Tohoku J Exp Med. 1963 Jul 25;80:118-34. [PubMed:14055140 ]

Associated OMIM IDs

181500 (Schizophrenia)
266600 (Crohn's disease)
610247 (Eosinophilic esophagitis)
276100 (Tryptophanuria with dwarfism)

External Links

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

VMH ID

LKYNR

MarkerDB ID

MDB00029988

Good Scents ID

Not Available

References

Synthesis Reference

Hayaishi, Osamu. L-Kynurenine sulfate monohydrate. Biochemical Preparations (1953), 3 108-11.

Material Safety Data Sheet (MSDS)

Not Available

General References

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. Epub 2003 Sep 9. [PubMed:12964115 ]
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. [PubMed:10834318 ]
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. [PubMed:10721102 ]
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. [PubMed:670356 ]
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. [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. [PubMed:9784247 ]
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. [PubMed:10721136 ]
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. [PubMed:10966936 ]
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. [PubMed:8583213 ]
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. [PubMed:10721103 ]
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. [PubMed:1422788 ]
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. [PubMed:8906267 ]
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 ]
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. [PubMed:15206719 ]
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Okuno E, Nakamura M, Schwarcz R: Two kynurenine aminotransferases in human brain. Brain Res. 1991 Mar 1;542(2):307-12. [PubMed:2029638 ]
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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. [PubMed:8785025 ]
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. Epub 2005 Aug 15. [PubMed:16099471 ]
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. [PubMed:12092667 ]
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 ]
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Enzymes

Enzyme Details

1. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Reactions

Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic acid	details

Enzyme Details

2. Kynureninase

General function:: Involved in metabolic process
Specific function:: Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:: KYNU
Uniprot ID:: Q16719
Molecular weight:: 34634.47

Reactions

Kynurenine + Water → 2-Aminobenzoic acid + L-Alanine	details

Enzyme Details

3. Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Transaminase with broad substrate specificity. Has transaminase activity towards aminoadipate, kynurenine, methionine and glutamate. Shows activity also towards tryptophan, aspartate and hydroxykynurenine. Accepts a variety of oxo-acids as amino-group acceptors, with a preference for 2-oxoglutarate, 2-oxocaproic acid, phenylpyruvate and alpha-oxo-gamma-methiol butyric acid. Can also use glyoxylate as amino-group acceptor (in vitro).
Gene Name:: AADAT
Uniprot ID:: Q8N5Z0
Molecular weight:: 47351.17

Reactions

Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic acid	details

Enzyme Details

4. Kynurenine--oxoglutarate transaminase 1

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:: CCBL1
Uniprot ID:: Q16773
Molecular weight:: 47874.765

Reactions

Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic acid	details

Enzyme Details

5. Aryl hydrocarbon receptor

General function:: Involved in transcription regulator activity
Specific function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:: AHR
Uniprot ID:: P35869
Molecular weight:: 96146.7

Enzyme Details

6. Kynurenine 3-monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the hydroxylation of L-kynurenine (L-Kyn) to form 3-hydroxy-L-kynurenine (L-3OHKyn). Required for synthesis of quinolinic acid, a neurotoxic NMDA receptor antagonist and potential endogenous inhibitor of NMDA receptor signaling in axonal targeting, synaptogenesis and apoptosis during brain development. Quinolinic acid may also affect NMDA receptor signaling in pancreatic beta cells, osteoblasts, myocardial cells, and the gastrointestinal tract.
Gene Name:: KMO
Uniprot ID:: O15229
Molecular weight:: 55809.445

Reactions

Kynurenine + NADPH + Oxygen → L-3-Hydroxykynurenine + NADP + Water	details
Kynurenine + Oxygen + NADPH + Hydrogen Ion → L-3-Hydroxykynurenine + NADP + Water	details

Enzyme Details

7. Aminoadipate aminotransferase, isoform CRA_b

General function:: Transcription
Specific function:: Not Available
Gene Name:: AADAT
Uniprot ID:: Q4W5N8
Molecular weight:: 47351.2

Enzyme Details

8. Kynurenine formamidase

General function:: Involved in hydrolase activity
Specific function:: Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites (By similarity).
Gene Name:: AFMID
Uniprot ID:: Q63HM1
Molecular weight:: 33991.5

Reactions

L-Formylkynurenine + Water → Formic acid + Kynurenine	details

Enzyme Details

9. Kynurenine--oxoglutarate transaminase 3

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:: CCBL2
Uniprot ID:: Q6YP21
Molecular weight:: 51399.855

Reactions

Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic acid	details
Kynurenine + Glyoxylic acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glycine	details

Showing metabocard for Kynurenine (HMDB0000684)

MOL for HMDB0000684 (Kynurenine)

3D MOL for HMDB0000684 (Kynurenine)

3D SDF for HMDB0000684 (Kynurenine)

3D-SDF for HMDB0000684 (Kynurenine)

PDB for HMDB0000684 (Kynurenine)

3D PDB for HMDB0000684 (Kynurenine)

SMILES for HMDB0000684 (Kynurenine)

INCHI for HMDB0000684 (Kynurenine)

Structure for HMDB0000684 (Kynurenine)

3D Structure for HMDB0000684 (Kynurenine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

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