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Showing NP-Card for Glutaconic acid (NP0000344)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:14:45 UTC
NP-MRD IDNP0000344
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlutaconic acid
DescriptionGlutaconic acid is related to the fully saturated glutaric acid and belongs to the class of compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Glutaconic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Glutaconic acid has been detected in the urine of individuals with inborn errors of metabolism. When present in sufficiently high levels, glutaconic acid can act as an acidogen, a neurotoxin, and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A neurotoxin is a compound that is toxic to neural tissues and cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of glutaconic acid are associated with glutaric aciduria type I (glutaric acidemia type I, glutaryl-CoA dehydrogenase deficiency, GA1, or GAT1). GA1 is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine and tryptophan. Excessive levels of their intermediate breakdown products (e.G. Glutaric acid, glutaryl-CoA, 3-hydroxyglutaric acid, glutaconic acid) can accumulate and cause damage to the brain (and also other organs). Babies with glutaric acidemia type I are often born with unusually large heads (macrocephaly). Macrocephaly is amongst the earliest signs of GA1. GA1 also causes secondary carnitine deficiency because glutaconic acid, like other organic acids, is detoxified by carnitine. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated glutaric aciduria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. Glutaconic acid's neurotoxicity is thought to be partially caused by an excitotoxic mechanism in which glutaconic acid overactivates N-methyl-D-aspartate (NMDA) receptors. Accumulating trans-glutaconic (TG) acids have been proposed to be involved in the development of the striatal degeneration seen in children with glutaric acidemia type I via an excitotoxic mechanism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000344 (Glutaconic acid)


  Mrv1652309042000042D          

  9  8  0  0  0  0            999 V2000
   10.8430   -8.0369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8430   -8.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1285   -9.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5575   -9.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2720   -8.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9865   -9.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7010   -8.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7010   -8.0369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4154   -9.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
M  END
Download

3D MOL for NP0000344 (Glutaconic acid)

HMDB0000620
     RDKit          3D
Glutaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -3.1002   -2.0466    0.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4408   -0.9791    0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1268    0.2104    0.5120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9827   -0.9895    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    0.1386    0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606    0.1229   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8910    0.7256    0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2134    1.1479    1.9140 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694    0.8113    0.9261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769    0.9353   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4476   -1.9146   -0.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8141    1.0629    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506   -0.8779   -0.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730    0.7942   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8248    0.8586    0.0900 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  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
  6 14  1  0
  9 15  1  0
M  END
Download

3D SDF for NP0000344 (Glutaconic acid)


  Mrv1652309042000042D          

  9  8  0  0  0  0            999 V2000
   10.8430   -8.0369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8430   -8.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1285   -9.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5575   -9.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2720   -8.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9865   -9.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7010   -8.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7010   -8.0369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4154   -9.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000344

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C\C=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+

> <INCHI_KEY>
XVOUMQNXTGKGMA-OWOJBTEDSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.0987

> <EXACT_MASS>
130.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.364693301928234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-pent-2-enedioic acid

> <ALOGPS_LOGP>
0.05

> <JCHEM_LOGP>
0.043909187333333426

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.5175481219684

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6919558338662966

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
29.231299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glutaconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000344 (Glutaconic acid)

HMDB0000620
     RDKit          3D
Glutaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -3.1002   -2.0466    0.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4408   -0.9791    0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1268    0.2104    0.5120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9827   -0.9895    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    0.1386    0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606    0.1229   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8910    0.7256    0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2134    1.1479    1.9140 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694    0.8113    0.9261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769    0.9353   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4476   -1.9146   -0.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8141    1.0629    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506   -0.8779   -0.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730    0.7942   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8248    0.8586    0.0900 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  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
  6 14  1  0
  9 15  1  0
M  END
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PDB for NP0000344 (Glutaconic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0      20.240 -15.002   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      20.240 -16.542   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      18.907 -17.312   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      21.574 -17.312   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.908 -16.542   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.241 -17.312   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.575 -16.542   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      25.575 -15.002   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      26.909 -17.312   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0000344 (Glutaconic acid)

COMPND    HMDB0000620
HETATM    1  O1  UNL     1      -3.100  -2.047   0.350  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.441  -0.979   0.316  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.127   0.210   0.512  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.983  -0.990   0.077  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.294   0.139   0.043  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.161   0.123  -0.196  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.891   0.726   0.945  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.213   1.148   1.914  1.00  0.00           O  
HETATM    9  O4  UNL     1       3.269   0.811   0.926  1.00  0.00           O  
HETATM   10  H1  UNL     1      -3.077   0.935  -0.201  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.448  -1.915  -0.075  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.814   1.063   0.193  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.551  -0.878  -0.446  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.373   0.794  -1.077  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.825   0.859   0.090  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    5   11
CONECT    5    6   12
CONECT    6    7   13   14
CONECT    7    8    8    9
CONECT    9   15
END
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SMILES for NP0000344 (Glutaconic acid)

OC(=O)C\C=C\C(O)=O
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INCHI for NP0000344 (Glutaconic acid)

InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+
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View in JSmol
Synonyms
ValueSource
(e)-GlutaconateChEBI
trans-GlutaconateChEBI
trans-Glutaconic acidChEBI
(e)-Glutaconic acidGenerator
GlutaconateGenerator
(e)-2-PentenedioateHMDB
(e)-2-Pentenedioic acidHMDB
1,3-PropenedicarboxylateHMDB
1,3-Propenedicarboxylic acidHMDB
1-Propene-1,3-dicarboxylateHMDB
1-Propene-1,3-dicarboxylic acidHMDB
PentenedioateHMDB
Pentenedioic acidHMDB
Glutaconic acid, (e)-isomerHMDB
2-PentendioateHMDB
2-Pentenedioic acidHMDB
Glutaconic acidHMDB
Chemical FormulaC5H6O4
Average Mass130.0987 Da
Monoisotopic Mass130.02661 Da
IUPAC Name(2E)-pent-2-enedioic acid
Traditional Nameglutaconic acid
CAS Registry Number1724-02-3
SMILES
OC(=O)C\C=C\C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+
InChI KeyXVOUMQNXTGKGMA-OWOJBTEDSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility17.6 g/LALOGPS
logP0.05ALOGPS
logP0.044ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)3.69ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.23 m³·mol⁻¹ChemAxon
Polarizability11.36 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000620
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022146
KNApSAcK IDC00052288
Chemspider ID4444138
KEGG Compound IDC02214
BioCyc IDGLUTACONATE
BiGG IDNot Available
Wikipedia LinkGlutaconic_acid
METLIN ID5593
PubChem Compound5280498
PDB IDNot Available
ChEBI ID15670
Good Scents IDNot Available
References
General References
  1. Podebrad F, Heil M, Beck T, Mosandl A, Sewell AC, Bohles H: Stereodifferentiation of 3-hydroxyisobutyric- and 3-aminoisobutyric acid in human urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry. Clin Chim Acta. 2000 Feb 25;292(1-2):93-105. [PubMed:10686279 ]
  2. Osaka H, Kimura S, Nezu A, Yamazaki S, Saitoh K, Yamaguchi S: Chronic subdural hematoma, as an initial manifestation of glutaric aciduria type-1. Brain Dev. 1993 Mar-Apr;15(2):125-7. [PubMed:8214331 ]
  3. Wang X, Wang X, Xie G, Zhou M, Yu H, Lin Y, Du G, Luo G, Jia W, Liu P: Urinary metabolite variation is associated with pathological progression of the post-hepatitis B cirrhosis patients. J Proteome Res. 2012 Jul 6;11(7):3838-47. doi: 10.1021/pr300337s. Epub 2012 Jun 7. [PubMed:22624806 ]
  4. Zhou P, Zhou L, Shi Y, Li Z, Liu L, Zuo L, Zhang J, Liang S, Kang J, Du S, Yang J, Sun Z, Zhang X: Neuroprotective Effects of Danshen Chuanxiongqin Injection Against Ischemic Stroke: Metabolomic Insights by UHPLC-Q-Orbitrap HRMS Analysis. Front Mol Biosci. 2021 May 7;8:630291. doi: 10.3389/fmolb.2021.630291. eCollection 2021. [PubMed:34026822 ]
  5. Kilavuz S, Bulut D, Kor D, Seker-Yilmaz B, Ozcan N, Incecik F, Onan B, Ceylaner G, Onenli-Mungan N: The outcome of 41 Late-Diagnosed Turkish GA-1 Patients: A Candidate for the Turkish NBS. Neuropediatrics. 2021 Feb 12. doi: 10.1055/s-0040-1722691. [PubMed:33578440 ]
  6. Lu Y, Shao M, Xiang H, Zheng P, Wu T, Ji G: Integrative transcriptomics and metabolomics explore the mechanism of kaempferol on improving nonalcoholic steatohepatitis. Food Funct. 2020 Nov 18;11(11):10058-10069. doi: 10.1039/d0fo02123g. [PubMed:33135718 ]
  7. Finsterer J, Scorza FA, Fiorini AC, Scorza CA: MEGDEL Syndrome. Pediatr Neurol. 2020 Sep;110:25-29. doi: 10.1016/j.pediatrneurol.2020.03.009. Epub 2020 Jul 16. [PubMed:32684373 ]
  8. Pereira R, Wei Y, Mohamed E, Radi M, Malina C, Herrgard MJ, Feist AM, Nielsen J, Chen Y: Adaptive laboratory evolution of tolerance to dicarboxylic acids in Saccharomyces cerevisiae. Metab Eng. 2019 Dec;56:130-141. doi: 10.1016/j.ymben.2019.09.008. Epub 2019 Sep 21. [PubMed:31550508 ]
  9. Roeben B, Schule R, Ruf S, Bender B, Alhaddad B, Benkert T, Meitinger T, Reich S, Bohringer J, Langhans CD, Vaz FM, Wortmann SB, Marquardt T, Haack TB, Krageloh-Mann I, Schols L, Synofzik M: SERAC1 deficiency causes complicated HSP: evidence from a novel splice mutation in a large family. J Med Genet. 2018 Jan;55(1):39-47. doi: 10.1136/jmedgenet-2017-104622. Epub 2017 Sep 15. [PubMed:28916646 ]