Showing Compound Xanthurenic acid (FDB022297)

Record Information

Version

1.0

Creation date

2011-09-21 00:11:43 UTC

Update date

2015-10-09 22:27:28 UTC

Primary ID

FDB022297

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Xanthurenic acid

Description

Xanthurenic acid, also known as xanthurenate or 8-hydroxykynurenate, 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. Xanthurenic acid is a very strong basic compound (based on its pKa). Xanthurenic acid exists in all living species, ranging from bacteria to humans. Xanthurenic acid, with regard to humans, has been found to be associated with several diseases such as hemodialysis, eosinophilic esophagitis, and colorectal cancer; xanthurenic acid has also been linked to the inborn metabolic disorder kynureninase deficiency.

CAS Number

59-00-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
4-oxoxanthurenic acid	hmdb
4,8-dihydroxy-Quinaldate	hmdb
4,8-dihydroxy-Quinaldic acid	hmdb
oxoxanthurenate	hmdb

Predicted 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

Chemical Formula

C10H7NO4

IUPAC name

4,8-dihydroxyquinoline-2-carboxylic acid

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

Isomeric SMILES

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

Average Molecular Weight

205.1669

Monoisotopic Molecular Weight

205.037507717

Classification

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

Endogenous

Biological location:

Tissue and substructures:

Epidermis

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Xanthurenic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0563900000-9a574c7d3effa0b19274	Spectrum
GC-MS	Xanthurenic acid, 3 TMS, GC-MS Spectrum	splash10-0a4i-1563900000-1b0b2fc6caac1ac637a5	Spectrum
GC-MS	Xanthurenic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0232900000-540a2f1838749e5da291	Spectrum
GC-MS	Xanthurenic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0563900000-9a574c7d3effa0b19274	Spectrum
GC-MS	Xanthurenic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-1563900000-1b0b2fc6caac1ac637a5	Spectrum
Predicted GC-MS	Xanthurenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06vi-0910000000-eb5f12387da253ffea09	Spectrum
Predicted GC-MS	Xanthurenic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-5009200000-7ce87a515165642720dd	Spectrum
Predicted GC-MS	Xanthurenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xanthurenic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

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

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.32 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum