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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:16 UTC

HMDB ID

HMDB0000881

Secondary Accession Numbers

HMDB00881

Metabolite Identification

Common Name

Xanthurenic acid

Description

Xanthurenic acid, also known as xanthurenate or 8-hydroxykynurenic acid, is a member of the class of compounds known as quinoline carboxylic acids. Quinoline carboxylic acids are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Xanthurenic acid is slightly soluble (in water). Xanthurenic acid can be found primarily in blood, feces, and urine, as well as in human epidermis tissue. Within the cell, xanthurenic acid is primarily located in the membrane. Xanthurenic acid exists in all eukaryotes, ranging from yeast to humans. In humans, xanthurenic acid is involved in the tryptophan metabolism. Moreover, xanthurenic acid is found to be associated with citrullinemia type I, which is an inborn error of metabolism. Xanthurenic acid is a metabolite from tryptophan catabolism. It is a substrate of the enzyme methyltransferases (EC 2.1.1.-) in pathway tryptophan metabolism (KEGG).

Structure

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

Xylulose-5-phosphate.mol
  Mrv1652305271900322D          

 15 16  0  0  0  0            999 V2000
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  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  1  0  0  0  0
 10 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  2  0  0  0  0
  1 14  2  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000881

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)

> <INCHI_KEY>
FBZONXHGGPHHIY-UHFFFAOYSA-N

> <FORMULA>
C10H7NO4

> <MOLECULAR_WEIGHT>
205.1669

> <EXACT_MASS>
205.037507717

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
19.064003634931545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dihydroxyquinoline-2-carboxylic acid

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
-0.16662861726590097

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.066086911279461

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1352227807412834

> <JCHEM_PKA_STRONGEST_BASIC>
5.753313640791366

> <JCHEM_POLAR_SURFACE_AREA>
90.65

> <JCHEM_REFRACTIVITY>
50.8253

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthurenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Xylulose-5-phosphate.mol                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2   14   15                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12    2                                                       
CONECT   14    1                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Xanthurenate	Kegg
8-Hydroxykynurenic acid	HMDB
Gametocyte activating factor (gaf)	HMDB
4,8-Dihydroxy-2-quinolinecarboxylate	HMDB
4,8-Dihydroxy-2-quinolinecarboxylic acid	HMDB
4,8-Dihydroxy-quinaldate	HMDB
4,8-Dihydroxy-quinaldic acid	HMDB
4,8-Dihydroxyquinaldate	HMDB
4,8-Dihydroxyquinaldic acid	HMDB
4,8-Dihydroxyquinaldinate	HMDB
4,8-Dihydroxyquinaldinic acid	HMDB
4,8-Dihydroxyquinoline-2-carboxylate	HMDB
4,8-Dihydroxyquinoline-2-carboxylic acid	HMDB
4-Oxoxanthurenic acid	HMDB
8-Hydroxykynurenate	HMDB
Oxoxanthurenate	HMDB
Xanthurate	HMDB
Xanthuric acid	HMDB

Chemical Formula

C₁₀H₇NO₄

Average Molecular Weight

205.1669

Monoisotopic Molecular Weight

205.037507717

IUPAC Name

4,8-dihydroxyquinoline-2-carboxylic acid

Traditional Name

xanthurenic acid

CAS Registry Number

59-00-7

SMILES

OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1

InChI Identifier

InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)

InChI Key

FBZONXHGGPHHIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Substituents

Quinoline-2-carboxylic acid
Dihydroquinolone
Hydroxyquinoline
8-hydroxyquinoline
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolinemonocarboxylic acid (CHEBI:10072 )
dihydroxyquinoline (CHEBI:10072 )

Ontology

Physiological effect

Health effect

Hemodialysis (HMDB: HMDB0000881)

Genetic disorder

Inborn errors of metabolism

Kynureninase deficiency (HMDB: HMDB0000881)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000881)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0000881)
Urine (HMDB: HMDB0000881)

Tissue

Epithelium

Epidermis (HMDB: HMDB0000881)

Cellular substructure

Cell membrane (HMDB: HMDB0000881)
Membrane (HMDB: HMDB0000881)

Source

Endogenous

Endogenous (HMDB: HMDB0000881)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (HMDB: HMDB0000881)
Tryptophan Metabolism (HMDB: HMDB0000881)

Role

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000273)
Kynureninase deficiency (MarkerDB: MDB00000273)
Hemodialysis (MarkerDB: MDB00000273)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	289 °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_neg	132.513	30932474
[M+H]+	MetCCS_train_pos	140.469	30932474
[M-H]-	Not Available	134.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000333
[M+H]+	Not Available	140.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000333

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.63 g/L	ALOGPS
logP	2.01	ALOGPS
logP	-0.17	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.14	ChemAxon
pKa (Strongest Basic)	5.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.65 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	50.83 m³·mol⁻¹	ChemAxon
Polarizability	19.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	145.772	31661259
DarkChem	[M-H]-	144.085	31661259
AllCCS	[M+H]+	143.632	32859911
AllCCS	[M-H]-	140.607	32859911
DeepCCS	[M+H]+	143.634	30932474
DeepCCS	[M-H]-	141.238	30932474
DeepCCS	[M-2H]-	174.513	30932474
DeepCCS	[M+Na]+	149.547	30932474
AllCCS	[M+H]+	143.6	32859911
AllCCS	[M+H-H2O]+	139.3	32859911
AllCCS	[M+NH4]+	147.6	32859911
AllCCS	[M+Na]+	148.8	32859911
AllCCS	[M-H]-	140.6	32859911
AllCCS	[M+Na-2H]-	140.5	32859911
AllCCS	[M+HCOO]-	140.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xanthurenic acid	OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1	3411.3	Standard polar	33892256
Xanthurenic acid	OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1	2040.7	Standard non polar	33892256
Xanthurenic acid	OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1	2045.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xanthurenic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O)=C2C=CC=C(O)C2=N1	2301.7	Semi standard non polar	33892256
Xanthurenic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC2=C(O)C=C(C(=O)O)N=C12	2272.1	Semi standard non polar	33892256
Xanthurenic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC(C(=O)O)=NC2=C(O)C=CC=C12	2267.1	Semi standard non polar	33892256
Xanthurenic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=C2C=CC=C(O)C2=N1	2200.9	Semi standard non polar	33892256
Xanthurenic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(O)=C2C=CC=C(O[Si](C)(C)C)C2=N1	2220.0	Semi standard non polar	33892256
Xanthurenic acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC(C(=O)O)=NC2=C(O[Si](C)(C)C)C=CC=C12	2241.8	Semi standard non polar	33892256
Xanthurenic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=C2C=CC=C(O[Si](C)(C)C)C2=N1	2257.8	Semi standard non polar	33892256
Xanthurenic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=C2C=CC=C(O)C2=N1	2558.9	Semi standard non polar	33892256
Xanthurenic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C(O)C=C(C(=O)O)N=C12	2563.2	Semi standard non polar	33892256
Xanthurenic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O)=NC2=C(O)C=CC=C12	2533.0	Semi standard non polar	33892256
Xanthurenic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C2C=CC=C(O)C2=N1	2767.0	Semi standard non polar	33892256
Xanthurenic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=C2C=CC=C(O[Si](C)(C)C(C)(C)C)C2=N1	2775.9	Semi standard non polar	33892256
Xanthurenic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O)=NC2=C(O[Si](C)(C)C(C)(C)C)C=CC=C12	2804.3	Semi standard non polar	33892256
Xanthurenic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C2C=CC=C(O[Si](C)(C)C(C)(C)C)C2=N1	3001.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Xanthurenic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0563900000-9a574c7d3effa0b19274	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Xanthurenic acid GC-MS (3 TMS)	splash10-0a4i-1563900000-1b0b2fc6caac1ac637a5	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Xanthurenic acid EI-B (Non-derivatized)	splash10-0a4i-0232900000-540a2f1838749e5da291	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Xanthurenic acid GC-EI-TOF (Non-derivatized)	splash10-0a4i-0563900000-9a574c7d3effa0b19274	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Xanthurenic acid GC-MS (Non-derivatized)	splash10-0a4i-1563900000-1b0b2fc6caac1ac637a5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vi-0910000000-eb5f12387da253ffea09	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (3 TMS) - 70eV, Positive	splash10-00di-5009200000-7ce87a515165642720dd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthurenic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4i-0590000000-e130e584059a7dd08226	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a59-0900000000-bd9a9768f7b716a5eb2b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-003r-5900000000-6120cbfe1c7c51793910	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0006-0910000000-15a7a4353f513ac53e48	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0006-0900000000-37c7cba5a7933c291829	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0006-0900000000-fb1104898a85e262eb32	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0006-1900000000-aa8f1e95e14bd25bb8c4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0006-3900000000-693b38057f05e771cc54	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-004i-0910000000-1b3d8f0b5d44d2f4f7fb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-qTOF , Positive-QTOF	splash10-001i-0900000000-c536b681ae0310232582	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QTOF , negative-QTOF	splash10-0udi-0390000000-14cea774f303a59fa905	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QTOF , negative-QTOF	splash10-03di-0900000000-15824b481226de9cecf2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QTOF , negative-QTOF	splash10-03di-0900000000-8f47ef6ebecafe34e315	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QTOF , negative-QTOF	splash10-07w9-0900000000-fbce68ee4689a56033fc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QTOF , negative-QTOF	splash10-00lr-0900000000-100f6b77c591b2664152	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QQ , negative-QTOF	splash10-0006-0910000000-15a7a4353f513ac53e48	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QQ , negative-QTOF	splash10-0006-0900000000-37c7cba5a7933c291829	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QQ , negative-QTOF	splash10-0006-0900000000-fb1104898a85e262eb32	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xanthurenic acid LC-ESI-QQ , negative-QTOF	splash10-0006-1900000000-aa8f1e95e14bd25bb8c4	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthurenic acid 10V, Positive-QTOF	splash10-0a4i-0590000000-726653998e487aeb2197	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthurenic acid 20V, Positive-QTOF	splash10-03di-0920000000-1851142dfaf7cd699152	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthurenic acid 40V, Positive-QTOF	splash10-03di-0900000000-734222988fd38fa8fcf1	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthurenic acid 10V, Negative-QTOF	splash10-0udi-0390000000-ae1209f92413230a3a3c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthurenic acid 20V, Negative-QTOF	splash10-0w29-0960000000-40a305f409d409092657	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthurenic acid 40V, Negative-QTOF	splash10-08gl-2900000000-21ba1ed88fab855ade65	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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

Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Epidermis

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.022 +/- 0.001 uM	Adult (>18 years old)	Not Specified	Normal	12092667	details
Blood	Detected and Quantified	0 uM	Children (1 - 13 years old)	Both	Normal	17334708	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	1.28 +/- 0.44 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19754154	details
Urine	Detected and Quantified	2.0 (0.0 - 4.0) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	17334708	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0550 (0.00400-0.100) umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	5.537 +/- 6.597 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.10 +/- 0.17 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	0.17 +/- 0.06 uM	Adult (>18 years old)	Both	Hemodialysis	12092667	details
Blood	Detected and Quantified	3.0 (2.0 - 4.0) uM	Children (1-13 years old)	Not Specified	Kynureninase deficiency	17334708	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Enthesitis-related arthritis	27786174	details
Urine	Detected and Quantified	200.0 (194.0 - 260.0) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Kynureninase deficiency	17334708	details
Urine	Detected and Quantified	5.643 +/- 3.642 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Hemodialysis
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 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Kynureninase deficiency
Christensen M, Duno M, Lund AM, Skovby F, Christensen E: Xanthurenic aciduria due to a mutation in KYNU encoding kynureninase. J Inherit Metab Dis. 2007 Apr;30(2):248-55. Epub 2007 Mar 1. [PubMed:17334708 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
236800 (Kynureninase deficiency)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022297

KNApSAcK ID

Not Available

Chemspider ID

5497

KEGG Compound ID

C02470

BioCyc ID

XANTHURENATE

BiGG ID

Not Available

Wikipedia Link

Xanthurenic_acid

METLIN ID

5841

PubChem Compound

5699

PDB ID

Not Available

ChEBI ID

10072

Food Biomarker Ontology

Not Available

VMH ID

C02470

MarkerDB ID

MDB00000273

Good Scents ID

Not Available

References

Synthesis Reference

Furst, Arthur; Olsen, Carl J. A convenient synthesis of xanthurenic acid. Journal of Organic Chemistry (1951), 16 412-14.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Igari T, Tsuchizawa M, Shimamura T: Alteration of tryptophan metabolism in the synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Tohoku J Exp Med. 1987 Oct;153(2):79-86. [PubMed:3500530 ]
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 ]
Bapurao S, Krishnaswamy K: Vitamin B6 nutritional status of pellagrins and their leucine tolerance. Am J Clin Nutr. 1978 May;31(5):819-24. [PubMed:206127 ]
Shibata K, Fukuwatari T, Murakami M, Sasaki R: Increase in conversion of tryptophan to niacin in pregnant rats. Adv Exp Med Biol. 2003;527:435-41. [PubMed:15206761 ]
Forrest CM, Gould SR, Darlington LG, Stone TW: Levels of purine, kynurenine and lipid peroxidation products in patients with inflammatory bowel disease. Adv Exp Med Biol. 2003;527:395-400. [PubMed:15206756 ]
Hoes MJ, Loeffen T, Vree TB: Kinetics of L-tryptophan in depressive patients: a possible correlation between the plasma concentrations of L-tryptophan and some psychiatric rating scales. Psychopharmacology (Berl). 1981;75(4):350-3. [PubMed:6803278 ]
Malina HZ, Hess OM: Xanthurenic acid translocates proapoptotic Bcl-2 family proteins into mitochondria and impairs mitochondrial function. BMC Cell Biol. 2004 Apr 6;5:14. [PubMed:15068490 ]
Bapurao S, Raman L, Tulpule PG: Biochemical assessment of vitamin B6 nutritional status in pregnant women with orolingual manifestations. Am J Clin Nutr. 1982 Oct;36(4):581-6. [PubMed:7124659 ]
Malina HZ: Comment on 'The photosensitiser xanthurenic acid is not present in normal human lenses' by P.G. Hains et al. [Exp. Eye Res. 77 (2003) 547-553]. Exp Eye Res. 2004 Sep;79(3):443-5; author reply 447-8. [PubMed:15336509 ]
Forrest CM, Kennedy A, Stone TW, Stoy N, Darlington LG: Kynurenine and neopterin levels in patients with rheumatoid arthritis and osteoporosis during drug treatment. Adv Exp Med Biol. 2003;527:287-95. [PubMed:15206742 ]

Enzymes

Enzyme Details

1. HemK methyltransferase family member 1

General function:: Not Available
Specific function:: N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:: HEMK1
Uniprot ID:: Q9Y5R4
Molecular weight:: Not Available

Reactions

Xanthurenic acid + S-Adenosylmethionine → 8-Methoxykynurenate + S-Adenosylhomocysteine	details

Enzyme Details

2. Methyltransferase-like protein 2B

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL2B
Uniprot ID:: Q6P1Q9
Molecular weight:: Not Available

Reactions

Xanthurenic acid + S-Adenosylmethionine → 8-Methoxykynurenate + S-Adenosylhomocysteine	details

Enzyme Details

3. Methyltransferase-like protein 6

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL6
Uniprot ID:: Q8TCB7
Molecular weight:: Not Available

Reactions

Xanthurenic acid + S-Adenosylmethionine → 8-Methoxykynurenate + S-Adenosylhomocysteine	details

Enzyme Details

4. Uncharacterized methyltransferase WBSCR22

General function:: Not Available
Specific function:: Methyltransferase that may act on DNA.
Gene Name:: WBSCR22
Uniprot ID:: O43709
Molecular weight:: Not Available

Reactions

Xanthurenic acid + S-Adenosylmethionine → 8-Methoxykynurenate + S-Adenosylhomocysteine	details

Showing metabocard for Xanthurenic acid (HMDB0000881)

MOL for HMDB0000881 (Xanthurenic acid)

3D MOL for HMDB0000881 (Xanthurenic acid)

3D SDF for HMDB0000881 (Xanthurenic acid)

3D-SDF for HMDB0000881 (Xanthurenic acid)

PDB for HMDB0000881 (Xanthurenic acid)

3D PDB for HMDB0000881 (Xanthurenic acid)

SMILES for HMDB0000881 (Xanthurenic acid)

INCHI for HMDB0000881 (Xanthurenic acid)

Structure for HMDB0000881 (Xanthurenic acid)

3D Structure for HMDB0000881 (Xanthurenic acid)

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

Reactions

Reactions

Reactions

Reactions