Showing metabocard for Quinolinic acid (MMDBc0000507)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:39:20 UTC
Update Date2024-10-09 19:22:51 UTC
Metabolite IDMMDBc0000507
Metabolite Identification
Common NameQuinolinic acid
DescriptionQuinolinic 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. It is also classified as a pyridine-2,3-dicarboxylic acid, which is a dicarboxylic acid with a pyridine backbone. Quinolinic acid is a colorless solid. In plants, it is the biosynthetic precursor to nicotine. Quinolinic acid is found in all organisms, from microbes to plants to animals. Quinolinic acid can be biosynthesized via aspartic acid in plants. Oxidation of aspartate by the enzyme aspartate oxidase gives iminosuccinate, containing the two carboxylic acid groups that are found in quinolinic acid. Condensation of iminosuccinate with glyceraldehyde-3-phosphate, mediated by quinolinate synthase, affords quinolinic acid Quinolinic acid is also a downstream product of the kynurenine pathway, which metabolizes the amino acid tryptophan ((PMID: 22678511 ). The kynurenine/tryptophan degradation pathway is important for its production of the coenzyme nicotinamide adenine dinucleotide (NAD+) and produces several neuroactive intermediates including quinolinic acid, kynurenine (KYN), kynurenic acid (KYNA), 3-hydroxykynurenine (3-HK), and 3-hydroxyanthranilic acid (3-HANA). In animals quinolinic acid acts as an NMDA receptor agonist and has a possible role in neurodegenerative disorders (PMID: 22678511 ). It also acts as a neurotoxin, gliotoxin, proinflammatory mediator, and pro-oxidant molecule (PMID: 22248144 ). Quinolinic acid can act as an endogenous brain excitotoxin when released by activated macrophages (PMID: 15013955 ). Within the brain, quinolinic acid is only produced by activated microglia and macrophages. Quinolinic acid is unable to pass through the blood-brain barrier (BBB) and must be produced within the brain by microglial cells or macrophages that have passed the BBB (PMID: 22248144 ). While quinolinic acid cannot pass through the BBB, kynurenic acid, tryptophan and 3-hydroxykynurenine can and can subsequently act as precursors to the production of quinolinic acid in the brain (PMID: 22248144 ). Quinolinic acid has potent neurotoxic effects. Studies have demonstrated that quinolinic acid may be involved in many psychiatric disorders and neurodegenerative diseases in the brain including ALS, Alzheimer’s disease, brain ischemia, Parkinson’s disease, Huntington’s disease and AIDS-dementia. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS. Indeed, levels of quinolinic acid in the CSF of AIDS patients suffering from AIDS-dementia can be up to twenty times higher than normal (PMID: 10936623 ). Quinolinic acid levels are increased in the brains of children infected with a range of bacterial infections of the central nervous system (CNS), of poliovirus patients, and of Lyme disease with CNS involvement patients. In addition, raised quinolinic acid levels have been found in traumatic CNS injury patients, patients suffering from cognitive decline with ageing, hyperammonaemia patients, hypoglycaemia patients, and systemic lupus erythematosus patients. Quinolinic acid has also been detected, but not quantified in, several different foods, such as Ceylon cinnamons, pitanga, Oregon yampahs, red bell peppers, and durians. This could make quinolinic acid a potential biomarker for the consumption of these foods.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f92520cd460>


  Mrv1652304272017442D          

 12 12  0  0  0  0            999 V2000
    1.2504   -0.1031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358   -0.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358   -1.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786   -0.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8932   -0.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931    1.1344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358    1.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503    0.7220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358    1.9594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f92520cd460>

HMDB0000232
     RDKit          3D
Quinolinic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
   -0.6362    2.9060   -0.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9864    1.6739   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3279    1.5684    0.1487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0511    0.6847   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3707    1.0614   -0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.1532   -0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0968   -1.1738   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8533   -1.5283    0.1001 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.6362    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4942   -1.1917    0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5661   -0.5960    0.5404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -2.5777    0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7301    2.1271    0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5044    2.1321   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677    0.4914   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9301   -1.8866   -0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0433   -3.2080    0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9  4  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
 12 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007f92520cd460>


  Mrv1652304272017442D          

 12 12  0  0  0  0            999 V2000
    1.2504   -0.1031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358   -0.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358   -1.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786   -0.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8932   -0.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931    1.1344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358    1.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503    0.7220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358    1.9594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000507

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C1=CC=CN=C1C(O)=O

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

> <INCHI_KEY>
GJAWHXHKYYXBSV-UHFFFAOYSA-N

> <FORMULA>
C7H5NO4

> <MOLECULAR_WEIGHT>
167.1189

> <EXACT_MASS>
167.021857653

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.34239790996518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridine-2,3-dicarboxylic acid

> <ALOGPS_LOGP>
0.15

> <JCHEM_LOGP>
-1.0261279053302073

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.095867548424451

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.30900716364465675

> <JCHEM_PKA_STRONGEST_BASIC>
5.743217331848265

> <JCHEM_POLAR_SURFACE_AREA>
87.49000000000001

> <JCHEM_REFRACTIVITY>
38.0415

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quinolinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f92520cd460>

HMDB0000232
     RDKit          3D
Quinolinic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
   -0.6362    2.9060   -0.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9864    1.6739   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3279    1.5684    0.1487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0511    0.6847   -0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3707    1.0614   -0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    0.1532   -0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0968   -1.1738   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8533   -1.5283    0.1001 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.6362    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4942   -1.1917    0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5661   -0.5960    0.5404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -2.5777    0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7301    2.1271    0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5044    2.1321   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677    0.4914   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9301   -1.8866   -0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0433   -3.2080    0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9  4  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
 12 17  1  0
M  END
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PDB for #<Metabolite:0x00007f92520cd460>

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  O   UNK     0       2.334  -0.192   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.000  -0.963   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.000  -2.503   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.333  -0.192   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.667  -0.962   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.001  -0.192   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.001   1.347   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.667   2.118   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.333   1.347   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.000   2.118   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.334   1.348   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.000   3.658   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for #<Metabolite:0x00007f92520cd460>

COMPND    HMDB0000232
HETATM    1  O1  UNL     1      -0.636   2.906  -0.360  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.986   1.674  -0.100  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.328   1.568   0.149  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.051   0.685  -0.120  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.371   1.061  -0.409  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.355   0.153  -0.432  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.097  -1.174  -0.172  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.853  -1.528   0.100  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.200  -0.636   0.138  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.494  -1.192   0.451  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.566  -0.596   0.540  1.00  0.00           O  
HETATM   12  O4  UNL     1      -1.544  -2.578   0.685  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.730   2.127   0.896  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.504   2.132  -0.605  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.368   0.491  -0.662  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.930  -1.887  -0.201  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.043  -3.208   0.102  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5    9
CONECT    5    6   14
CONECT    6    7    7   15
CONECT    7    8   16
CONECT    8    9    9
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   17
END
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SMILES for #<Metabolite:0x00007f92520cd460>

OC(=O)C1=CC=CN=C1C(O)=O
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INCHI for #<Metabolite:0x00007f92520cd460>

InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
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Synonyms
ValueSource
2,3-Pyridinedicarboxylic acidChEBI
Pyridine-2,3-dicarboxylateChEBI
2,3-PyridinedicarboxylateGenerator
QuinolinateGenerator
Pyridine-2,3-dicarboxylic acidGenerator
3,4-Pyridinedicarboxylic acidHMDB
Pyridin-2,3-dicarbonsaeureHMDB
Pyridine-2,3-carboxylateHMDB
Quinolinic acidHMDB
Molecular FormulaC7H5NO4
Average Mass167.1189
Monoisotopic Mass167.021857653
IUPAC Namepyridine-2,3-dicarboxylic acid
Traditional Namequinolinic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=CN=C1C(O)=O
InChI Identifier
InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
InChI KeyGJAWHXHKYYXBSV-UHFFFAOYSA-N