Quinolinic acid (YMDB00007)

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Identification

YMDB ID

YMDB00007

Name

Quinolinic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Quinolinic acid, also known as quinolinate, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Quinolinic acid is a very strong basic compound (based on its pKa). Quinolinic acid exists in all living species, ranging from bacteria to humans. quinolinic acid and phosphoribosyl pyrophosphate can be converted into nicotinic acid mononucleotide through the action of the enzyme nicotinate-nucleotide pyrophosphorylase [carboxylating]. In yeast, quinolinic acid is involved in the metabolic pathway called the nad metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2,3-pyridinedicarboxylate
2,3-pyridinedicarboxylic acid
3,4-Pyridinedicarboxylic acid
Pyridin-2,3-dicarbonsaeure
pyridine-2,3-carboxylate
Pyridine-2,3-dicarboxylate
Pyridine-2,3-dicarboxylic acid
Pyridine-3,4-dicarboxylic acid
Quinolinate
Quinolinic acid
Quinolinic acid, copper(2+) salt
Quinolinic acid, disodium salt
Quinolinic acid, strontium salt

CAS number

89-00-9

Weight

Average: 167.1189
Monoisotopic: 167.021857653

InChI Key

GJAWHXHKYYXBSV-UHFFFAOYSA-N

InChI

InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)

IUPAC Name

pyridine-2,3-dicarboxylic acid

Traditional IUPAC Name

quinolinic acid

Chemical Formula

C₇H₅NO₄

SMILES

[H]OC(=O)C1=NC([H])=C([H])C([H])=C1C(=O)O[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents

Substituents

Pyridine carboxylic acid
Dicarboxylic acid or derivatives
Heteroaromatic compound
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridinedicarboxylic acid (CHEBI:16675 )

Physical Properties

State

Solid

Charge

Melting point

190 °C

Experimental Properties

Property	Value	Reference
Water Solubility	11 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	4.07 g/L	ALOGPS
logP	0.15	ALOGPS
logP	-1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	0.31	ChemAxon
pKa (Strongest Basic)	5.74	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	38.04 m³·mol⁻¹	ChemAxon
Polarizability	14.34 Å³	ChemAxon
Number of Rings	1	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

Cytoplasm, Nucleus

Organoleptic Properties

Not Available

SMPDB Pathways

NAD metabolism	PW002421
Tryptophan metabolism	PW002442
beta-Alanine metabolism	PW002381

KEGG Pathways

Nicotinate and nicotinamide metabolism	ec00760
Tryptophan metabolism	ec00380
beta-Alanine metabolism	ec00410

SMPDB Reactions

Quinolinic acid + hydron + Phosphoribosyl pyrophosphate → Pyrophosphate + Carbon dioxide + Nicotinic acid mononucleotide

KEGG Reactions

Quinolinic acid + Phosphoribosyl pyrophosphate + hydron → Pyrophosphate + Carbon dioxide + Nicotinic acid mononucleotide

Dihydroxyacetone phosphate + Iminoaspartic acid → water + Quinolinic acid + phosphate

2-amino-3-(3-oxoprop-1-enyl)but-2-enedioate → Quinolinic acid + water + hydron

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) (2 TMS)	splash10-0002-0910000000-a8eacf1916c539d286b6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0910000000-64e9e4b901dd69dc90c5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006t-7910000000-0bb1a7ce8a5907feae21	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i0-9500000000-555e92ebc410fc53e92f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0100-5900000000-3d726d602fec21fd8beb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-a8eacf1916c539d286b6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-64e9e4b901dd69dc90c5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-7910000000-0bb1a7ce8a5907feae21	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1960000000-8197ee161fa149deabdd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-40d676712c981904799f	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g4j-4900000000-40b629f8c2ff96d454dc	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9680000000-e45ac969fff3f654bb49	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-0900000000-4a6d37bd8578b50cf677	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9100000000-45dc448cbedc6465ad63	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-2aa35085995bdc1801da	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-d0eb03bdfeea6084e0db	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0100-5900000000-7d59ce683134a6f33e8d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00or-9700000000-c13d2a2f6361459932db	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-016r-8900000000-d7f12324cf02b0023aed	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00or-9600000000-d51ee74ca89d43da53b4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udi-1900000000-a44a9d75afd871a62687	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0a4r-4900000000-1b71b709786880019164	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-5900000000-56f78a7bdb3c091573a7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a6r-9500000000-8140904c5eb795e92371	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9100000000-1175e50dbd23fc2a9922	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-0900000000-9a963e41421edb041561	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-0900000000-4c0c9b98c2ce00d0d282	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-d0eb03bdfeea6084e0db	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0100-5900000000-4af865513d09a8bab44f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00or-9700000000-c13d2a2f6361459932db	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-016r-8900000000-ff25a1c9823ecb018549	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-f9e1437d75c6f5b25d88	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1900000000-ad80f96e7d85d594f6cb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-9300000000-57792ffddc2cccbd77b9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-0900000000-343bdc632cd1916d92c9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-4900000000-c83c2058ae8923828aa6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00os-9100000000-840c225c8204e80727f2	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,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Panozzo, C., Nawara, M., Suski, C., Kucharczyka, R., Skoneczny, M., Becam, A. M., Rytka, J., Herbert, C. J. (2002). "Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae." FEBS Lett 517:97-102.12062417
di Luccio, E., Wilson, D. K. (2008). "Comprehensive X-ray structural studies of the quinolinate phosphoribosyl transferase (BNA6) from Saccharomyces cerevisiae." Biochemistry 47:4039-4050.18321072

Synthesis Reference:

Akhmerova, S. G.; Islamgulova, V. R.; Koksharov, V. G.; Sapozhnikov, Yu. E.; Manaeva, R. M. Methods of preparation of quinolinic acid. Bashkirskii Khimicheskii Zhurnal (2001), 8(2), 9-14.

External Links:

Resource	Link
CHEBI ID	16675
HMDB ID	HMDB00232
Pubchem Compound ID	1066
Kegg ID	C03722
ChemSpider ID	1037
FOODB ID	FDB031142
Wikipedia	Quinolinic_acid
BioCyc ID	QUINOLINATE

Enzymes

Protein Details

1. Nicotinate-nucleotide pyrophosphorylase [carboxylating]

General function:: Involved in catalytic activity
Specific function:: Involved in the catabolism of quinolinic acid (QA)
Gene Name:: BNA6
Uniprot ID:: P43619
Molecular weight:: 32364.69922

Reactions

Nicotinate D-ribonucleotide + diphosphate + CO(2) → pyridine-2,3-dicarboxylate + 5-phospho-alpha-D-ribose 1-diphosphate.

Structure for #<Compound:0xaa60b594>

Enzymes

Reactions