Kynurenic acid (YMDB01725)

Identification

YMDB ID

YMDB01725

Name

Kynurenic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Kynurenic acid, also known as kynurenate, 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. Kynurenic acid exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Kynurenic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-Carboxy-4-hydroxyquinoline
2-Quinolinecarboxylic acid, 4-hydroxy-
4-Hydroxy-2-chinolincarbonsaeure
4-hydroxy-2-quinolinecarboxylic acid
4-hydroxy-Quinaldate
4-hydroxy-Quinaldic acid
4-Hydroxyquinaldate
4-Hydroxyquinaldic acid
4-Hydroxyquinaldinate
4-Hydroxyquinaldinic acid
4-Hydroxyquinoline-2-carboxylate
4-Hydroxyquinoline-2-carboxylic acid
Kinurenic acid
kynurenate
Kynurenic acid
Kynurensaeure
Kynuronic acid
Quinaldic acid, 4-hydroxy-
Quinurenic acid
TRANSTORINE
4-Hydroxy-2-quinolinecarboxylate
Acid, kynurenic

CAS number

492-27-3

Weight

Average: 189.1675
Monoisotopic: 189.042593095

InChI Key

HCZHHEIFKROPDY-UHFFFAOYSA-N

InChI

InChI=1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)

IUPAC Name

4-oxo-1,4-dihydroquinoline-2-carboxylic acid

Traditional IUPAC Name

acid, kynurenic

Chemical Formula

C₁₀H₇NO₃

SMILES

OC(=O)C1=CC(=O)C2=C(N1)C=CC=C2

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
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monohydroxyquinoline (CHEBI:18344 )
quinolinemonocarboxylic acid (CHEBI:18344 )

Physical Properties

State

Solid

Charge

Melting point

280 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.95 g/L	ALOGPS
logP	1.16	ALOGPS
logP	1.58	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	52.32 m³·mol⁻¹	ChemAxon
Polarizability	18.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-1985000000-f1c74ffc481c3d0faaa2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0159-3895000000-6ba2750c5a9d9754abcc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0159-0498000000-3db9df2c3d8456d7ba63	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1985000000-f1c74ffc481c3d0faaa2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-3895000000-6ba2750c5a9d9754abcc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1895000000-e25b66b0b42d1928cc67	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02ga-1900000000-8c67ab2acdc02b88af2b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9740000000-a7c5c056d48055e0d44f	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-7a5c54ced5b83f291e67	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-0900000000-e6b451ee354ed2717160	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9500000000-887e5157431b2908f31e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0006-1900000000-06f7059894cc245cb344	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0006-0900000000-89a88f44f08b8b68d5c1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-014l-0900000000-3a256522dd8694fe04c0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000f-0900000000-a4b194b85fef656b9b65	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-7862c532805b6036dc67	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-5fe3171fdaece30b78c8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-df3b5b36289798800ad8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-d4c11672b9479b2cd4b6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-89a88f44f08b8b68d5c1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0006-0900000000-9c26ffa9c04aa03d60f5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0006-0900000000-6a8662ef19d900499a55	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0006-0900000000-d69a430b0eb34f38ad54	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0900000000-d0ef7c769d4985e85667	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01ox-0900000000-2a593c8017254be4a387	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01ox-0900000000-59f3559c0b95c9411d2c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-02tc-0900000000-57dbbfb8e12c60951d77	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-878dcda0ee5ec971fa72	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-92fe5294ec4a771f14e0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-1900000000-fa8b36fb6db8e403b711	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-9cede81ef6dfc45f5f7a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-0900000000-0d5cf046565b518442d5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-2900000000-2c420ff1e59666527005	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	18344
HMDB ID	HMDB00715
Pubchem Compound ID	3845
Kegg ID	C01717
ChemSpider ID	3712
FOODB ID	FDB022200
Wikipedia ID	Kynurenic_acid
BioCyc ID	Not Available

Structure for #<Compound:0xa377f7ec>