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Xanthurenic acid - 96%, high purity , CAS No.59-00-7
Selectively activates group II mGlu receptors
Basic Description
Synonyms
BDBM50113313 | Xanthurenate; 8-Hydroxykynurenic acid; 4,8-Dihydroxyquinaldic acid | 4-oxoxanthurenic acid | IDI1_000262 | NSC401570 | NSC-401570 | KBioSS_000733 | NCGC00094846-05 | 4,8-Dihydroxy-2-quinolinecarboxylic acid | 4,8-Dihydroxy-quinoline-2-carbo
Specifications & Purity
≥96%
Biochemical and Physiological Mechanisms
Shown to selectively activate group II mGlu receptors in transfected HEK293 cells at nanomolar concentrations. Attenuates cAMP formation in mouse cortical slices expressing mGlu2and mGlu3receptors.
Shipped In
Normal
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Organoheterocyclic compounds
Class
Quinolines and derivatives
Subclass
Quinoline carboxylic acids
Intermediate Tree Nodes
Not available
Direct Parent
Quinoline carboxylic acids
Alternative Parents
8-hydroxyquinolines Hydroxyquinolines Hydroquinolones Hydroquinolines Pyridinecarboxylic acids 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Vinylogous amides Heteroaromatic compounds Azacyclic compounds Carboxylic acids Monocarboxylic acids and derivatives Organooxygen compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Organonitrogen compounds
Molecular Framework
Aromatic heteropolycyclic compounds
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
Description
This compound 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.
External Descriptors
quinolinemonocarboxylic acid - dihydroxyquinoline
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
IUPAC Name
8-hydroxy-4-oxo-1H-quinoline-2-carboxylic acid
INCHI
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)
InChIKey
FBZONXHGGPHHIY-UHFFFAOYSA-N
Smiles
C1=CC2=C(C(=C1)O)NC(=CC2=O)C(=O)O
Isomeric SMILES
C1=CC2=C(C(=C1)O)NC(=CC2=O)C(=O)O
WGK Germany
3
RTECS
UZ9275000
PubChem CID
5699
Molecular Weight
205.17
Beilstein
185954
Reaxy-Rn
185954
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Solubility
Solvent:DMSO, Max Conc. mg/mL: 20.52, Max Conc. mM: 100
Melt Point(°C)
297-298°C
Molecular Weight
205.170 g/mol
XLogP3
0.900
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
1
Exact Mass
205.038 Da
Monoisotopic Mass
205.038 Da
Topological Polar Surface Area
86.600 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
336.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Citations of This Product
1.
Dan-Qian Chen,Gang Cao,Hua Chen,Dan Liu,Wei Su,Xiao-Yong Yu,Nosratola D Vaziri,Xiu-Hua Liu,Xu Bai,Li Zhang,Ying-Yong Zhao.
(2017-03-28)
Gene and protein expressions and metabolomics exhibit activated redox signaling and wnt/β-catenin pathway are associated with metabolite dysfunction in patients with chronic kidney disease.. Redox biology,
12
(505-521).
2.
Li Yueyue, Li Jingjie, Shi Yuhuan, Zhou Xuhui, Feng Wanqing, Han Lu, Ma Daqing, Jiang Hong, Yuan Yongfang.
(2022)
Urinary Aromatic Amino Acid Metabolites Associated With Postoperative Emergence Agitation in Paediatric Patients After General Anaesthesia: Urine Metabolomics Study. Frontiers in Pharmacology,
13
3.
Xiaoxu Cheng, Zifeng Pi, Zhong Zheng, Shu Liu, Fengrui Song, Zhiqiang Liu.
(2022)
Combined 16S rRNA gene sequencing and metabolomics to investigate the protective effects of Wu-tou decoction on rheumatoid arthritis in rats. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,
1199
(123249).
4.
Xue-Mei Han, Yan-Jie Qin, Ying Zhu, Xin-Lin Zhang, Nan-Xi Wang, Ying Rang, Xue-Jia Zhai, Yong-Ning Lu.
(2019)
Development of an underivatized LC-MS/MS method for quantitation of 14 neurotransmitters in rat hippocampus, plasma and urine: Application to CUMS induced depression rats. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,
174
(683).
5.
Dezhen Wang, Xinru Wang, Ping Zhang, Yao Wang, Renke Zhang, Jin Yan, Zhiqiang Zhou, Wentao Zhu.
(2017)
The fate of technical-grade chlordane in mice fed a high-fat diet and its roles as a candidate obesogen. ENVIRONMENTAL POLLUTION,
222
(532).
6.
Yao Wang,Wentao Zhu,Jing Qiu,Xinru Wang,Ping Zhang,Jin Yan,Zhiqiang Zhou.
(2015-04-13)
Monitoring tryptophan metabolism after exposure to hexaconazole and the enantioselective metabolism of hexaconazole in rat hepatocytes in vitro.. Journal of hazardous materials,
295
(9-16).
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6 Citations
H2429089