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Quinolinic Acid

AlkaPlorer ID: AK018597

Synonym: None

IUPAC Name: pyridine-2,3-dicarboxylate

Structure

SMILES: O=C([O-])C1=C(C(=O)[O-])N=CC=C1

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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)/p-2

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InChIKey: GJAWHXHKYYXBSV-UHFFFAOYSA-L

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Properties Information

Molecule Weight: 165.104

TPSA？: 93.15

MolLogP？: -2.191399999999999

Number of H-Donors: 0

Number of H-Acceptors: 5

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Aeromonas hydrophila Beta-lactamase Activity 130.0 % 10.1128/aac.00866-06
Aeromonas hydrophila Beta-lactamase Ki 200000.0 nM 10.1128/aac.00866-06
Agaricus bisporus Tyrosinase Inhibition 98.0 % 10.1021/jm101266s
Bacillus anthracis Anthrax lethal factor Inhibition 49.0 % 10.1021/jm101266s
Bacillus anthracis Anthrax lethal factor Potency 12589.3 nM None
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 89125.1 nM None
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 629.5 nM None
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 15811.4 nM None
Homo sapiens Advanced glycosylation end product-specific receptor Kd 43.0 nM 10.1021/acs.jmedchem.7b00058
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 14988.9 nM None
Homo sapiens Arachidonate 15-lipoxygenase Potency 39810.7 nM None
Homo sapiens Arachidonate 5-lipoxygenase Inhibition 30.0 % 10.1021/jm101266s
Homo sapiens Bloom syndrome protein Potency 100000.0 nM None
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 6309.6 nM None
Homo sapiens Cerebroside-sulfatase Potency 849.2 nM None
Homo sapiens Chromobox protein homolog 1 Potency 2818.4 nM None
Homo sapiens Cytochrome P450 1A2 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 Potency 1584.9 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 84367.9 nM None
Homo sapiens DNA polymerase iota Potency 39810.7 nM None
Homo sapiens Flap endonuclease 1 Potency 4744.4 nM None
Homo sapiens Flap endonuclease 1 Potency 89125.1 nM None
Homo sapiens Histone deacetylase 6 Inhibition -0.23 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 0.83 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 1584.9 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 3548.1 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 19952.6 nM None
Homo sapiens Lethal(3)malignant brain tumor-like protein 1 Potency 22387.2 nM None
Homo sapiens Lysine-specific demethylase 4A Potency 891.3 nM None
Homo sapiens Lysine-specific demethylase 4D-like IC50 10000000.0 nM 10.1021/acs.jmedchem.1c01694
Homo sapiens Lysine-specific demethylase 4D-like Potency 891.3 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 1778.3 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 1995.3 nM None
Homo sapiens Matrix metalloproteinase-1 Inhibition 4.0 % 10.1021/jm101266s
Homo sapiens Matrix metalloproteinase-2 Inhibition -16.0 % 10.1021/jm101266s
Homo sapiens Matrix metalloproteinase 3 Inhibition 82.0 % 10.1021/jm101266s
Homo sapiens Matrix metalloproteinase 8 Inhibition 14.0 % 10.1021/jm101266s
Homo sapiens Matrix metalloproteinase 9 Inhibition -8.0 % 10.1021/jm101266s
Homo sapiens Microtubule-associated protein tau Potency 1122.0 nM None
Homo sapiens Microtubule-associated protein tau Potency 1412.5 nM None
Homo sapiens Microtubule-associated protein tau Potency 15848.9 nM None
Homo sapiens Neuropeptide S receptor Potency 1000.0 nM None
Homo sapiens Regulator of G-protein signaling 4 Potency 9466.2 nM None
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 14125.4 nM None
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 35481.3 nM None
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 103.91 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 104.17 % 10.1124/mol.112.084152
Homo sapiens Thyroid stimulating hormone receptor Potency 5011.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 84.1 nM None
Mus musculus Mus musculus Activity 263.0 pg/ml 10.1073/pnas.0709261104
Mus musculus Mus musculus Activity 312.0 pg/ml 10.1073/pnas.0709261104
Mus musculus Mus musculus Activity 335000.0 None 10.1073/pnas.0709261104
Mus musculus Nitric oxide synthase, inducible Inhibition 5.0 % 10.1021/jm101266s
Plasmodium falciparum Plasmodium falciparum Potency 18526.0 nM None
Pseudomonas aeruginosa Metallo beta-lactamase Activity 67.0 % 10.1128/aac.00866-06
Pseudomonas aeruginosa Metallo beta-lactamase Activity 89.0 % 10.1128/aac.00866-06
Rattus norvegicus Advanced glycosylation end product-specific receptor Kd 43.0 nM 10.1021/acs.jmedchem.7b00058
Rattus norvegicus Glutamate NMDA receptor EC50 nan nM 10.1021/jm00046a009
Rattus norvegicus Glutamate NMDA receptor IC50 100000.0 nM 10.1021/jm00046a009
Rattus norvegicus Glutamate NMDA receptor IC50 100000.0 nM 10.1021/jm00086a004
Rattus norvegicus Glutamate [NMDA] receptor subunit epsilon 3 pKa 2.0 None 10.1021/jm00046a009
Rattus norvegicus Glutamate receptor ionotropic, AMPA IC50 100000.0 nM 10.1021/jm00046a009
Rattus norvegicus Rattus norvegicus EC50 1500000.0 nM 10.1021/jm00046a009
Rattus norvegicus Rattus norvegicus Enzyme activity 53.0 % 10.1021/jm00105a019
Rattus norvegicus Rattus norvegicus Enzyme activity 61.0 % 10.1021/jm00105a019
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 316.2 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 446.7 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 11.0 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 11.27 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -15.45 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.07 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.16 % 10.6019/CHEMBL4495565
Stenotrophomonas maltophilia Beta-lactamase L1 Activity 93.0 % 10.1128/aac.00866-06
None Unchecked Activity 4.19 ng/ml 10.1073/pnas.0709261104
None Unchecked Activity 8.36 ng/ml 10.1073/pnas.0709261104
None Unchecked Activity 11.3 ng/ml 10.1073/pnas.0709261104
None Unchecked Activity 15.4 ng/ml 10.1073/pnas.0709261104
None Unchecked Activity 62.0 % 10.1128/aac.00866-06
None Unchecked Activity 73.0 % 10.1128/aac.00866-06
None Unchecked Activity 98.0 % 10.1128/aac.00866-06
None Unchecked Activity 106.0 % 10.1128/aac.00866-06
None Unchecked IC50 479000.0 nM 10.1021/acs.jmedchem.1c01694
None Unchecked IC50 5000000.0 nM 10.1021/jm800936s
None Unchecked IC50 10000000.0 nM 10.1021/jm800936s
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked Ki nan None 10.1128/aac.00866-06
None Unchecked Potency 20.0 nM None
None Unchecked Potency 707.9 nM None
None Unchecked Potency 4109.5 nM None
None Unchecked Potency 8912.5 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT015833 N/C(C(=O)O)=C(/C=C\C=O)C(=O)O>>O=C(O)c1cccnc1C(=O)O R04293
AKRT015834 N/C(C(=O)O)=C(\C=C\C=O)C(=O)O>>O=C(O)c1cccnc1C(=O)O RXN-5721
AKRT015839 N=C(CC(=O)O)C(=O)O.O=C(CO)COP(=O)(O)O>>O=C(O)c1cccnc1C(=O)O QUINOLINATE-SYNTHA-RXN
AKRT018684 N[C@@H](CC(=O)O)C(=O)O.O=C(CO)COP(=O)(O)O>>O=C(O)c1cccnc1C(=O)O QUINOLINATE-SYNTHE-MULTI-RXN
AKRT020553 Nc1c(O)cccc1C(=O)O>>O=C(O)c1cccnc1C(=O)O 32283
AKRT023336 O=C(O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1.O=C=O>>O=C(O)c1cccnc1C(=O)O enzymemap_38555
AKRT023374 O=C(O)c1cccnc1.O=C=O>>O=C(O)c1cccnc1C(=O)O MNXR134285
AKRT023386 O=C(O)c1cccnc1C(=O)O.O=P(O)(O)OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)O)[C@H](O)[C@@H]1O>>O=C(O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1 QUINOPRIBOTRANS-RXN
AKRT023387 O=C(O)c1cccnc1C(=O)O.O=P(O)(O)OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)O)[C@H](O)[C@@H]1O>>O=C(O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1.O=C=O None
AKRT023388 O=C(O)c1cccnc1C(=O)O>>C#[O+] MNXR179799
AKRT023389 O=C(O)c1cccnc1C(=O)O>>N=C(CC(=O)O)C(=O)O MNXR179389
AKRT023390 O=C(O)c1cccnc1C(=O)O>>N[C@@H](CC(=O)O)C(=O)O MNXR137735
AKRT023391 O=C(O)c1cccnc1C(=O)O>>O=C(CO)COP(=O)(O)O MNXR137735
AKRT023392 O=C(O)c1cccnc1C(=O)O>>O=C=O QUINOPRIBOTRANS-RXN
AKRT023838 O=P(O)(O)OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)O)[C@H](O)[C@@H]1O.O=C(O)c1cccnc1C(=O)O>>O=C(O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1 enzymemap_38551