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Showing metabocard for Oxalacetic acid (HMDB0000223)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:37 UTC
HMDB IDHMDB0000223
Secondary Accession Numbers
  • HMDB00223
Metabolite Identification
Common NameOxalacetic acid
DescriptionOxalacetic acid, also known as oxaloacetic acid, keto-oxaloacetate or 2-oxobutanedioate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Oxalacetic acid is a metabolic intermediate in many processes that occur in animals and plants. It takes part in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, fatty acid synthesis and the citric acid cycle. Oxalacetic acid exists in all living species, ranging from bacteria to plants to humans. Within humans, oxalacetic acid participates in a number of enzymatic reactions. In particular, oxalacetic acid is an intermediate of the citric acid cycle, where it reacts with acetyl-CoA to form citrate, catalyzed by citrate synthase. It is also involved in gluconeogenesis and the urea cycle. In gluconeogenesis oxaloacetate is decarboxylated and phosphorylated by phosphoenolpyruvate carboxykinase and becomes 2-phosphoenolpyruvate using guanosine triphosphate (GTP) as phosphate source. In the urea cycle, malate is acted on by malate dehydrogenase to become oxaloacetate, producing a molecule of NADH. After that, oxaloacetate can be recycled to aspartate, as this recycling maintains the flow of nitrogen into the cell. In mice, injections of oxalacetic acid have been shown to promote brain mitochondrial biogenesis, activate the insulin signaling pathway, reduce neuroinflammation and activate hippocampal neurogenesis (PMID: 25027327 ). Oxalacetic acid has also been reported to reduce hyperglycemia in type II diabetes and to extend longevity in C. elegans (PMID: 25027327 ). Outside of the human body, oxalacetic acid has been detected, but not quantified in, several different foods, such as Persian limes, lemon balms, wild rice, canola, and peanuts. This could make oxalacetic acid a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000223 (Oxalacetic acid)

Oxalacetic acid.mol
  Mrv1652309032023572D          

  9  8  0  0  0  0            999 V2000
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
M  END
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3D MOL for HMDB0000223 (Oxalacetic acid)

HMDB0000223
     RDKit          3D
Oxalacetic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.9886    0.3792    0.0182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8381   -0.0828    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6103   -1.4346    0.4064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    0.8723    0.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5759    0.2116    0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238   -0.1292    1.7478 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5550   -0.0524   -0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3570    0.2648   -1.6634 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7455   -0.6687   -0.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0624   -2.0923   -0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6252    1.4626   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700    1.6150    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6602   -0.3456   -0.4278 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  9 13  1  0
M  END
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3D SDF for HMDB0000223 (Oxalacetic acid)

Oxalacetic acid.mol
  Mrv1652309032023572D          

  9  8  0  0  0  0            999 V2000
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000223

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)

> <INCHI_KEY>
KHPXUQMNIQBQEV-UHFFFAOYSA-N

> <FORMULA>
C4H4O5

> <MOLECULAR_WEIGHT>
132.0716

> <EXACT_MASS>
132.005873238

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
10.062860517055482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxobutanedioic acid

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-0.0418976006666667

> <ALOGPS_LOGS>
-0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.5760343878793956

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4098313234932576

> <JCHEM_PKA_STRONGEST_BASIC>
-9.874004724451435

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
24.333800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.71e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxalacetate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000223 (Oxalacetic acid)

HMDB0000223
     RDKit          3D
Oxalacetic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.9886    0.3792    0.0182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8381   -0.0828    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6103   -1.4346    0.4064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    0.8723    0.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5759    0.2116    0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238   -0.1292    1.7478 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5550   -0.0524   -0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3570    0.2648   -1.6634 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7455   -0.6687   -0.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0624   -2.0923   -0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6252    1.4626   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700    1.6150    1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6602   -0.3456   -0.4278 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  9 13  1  0
M  END
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PDB for HMDB0000223 (Oxalacetic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Oxalacetic acid.mol                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.667  -1.925   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.001   0.385   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.001  -1.925   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.334   0.385   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.001   1.925   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.334  -0.385   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    8    9                                                  
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0000223 (Oxalacetic acid)

COMPND    HMDB0000223
HETATM    1  O1  UNL     1      -2.989   0.379   0.018  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.838  -0.083   0.238  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.610  -1.435   0.406  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.723   0.872   0.312  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.576   0.212   0.568  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.824  -0.129   1.748  1.00  0.00           O  
HETATM    7  C4  UNL     1       1.555  -0.052  -0.470  1.00  0.00           C  
HETATM    8  O4  UNL     1       1.357   0.265  -1.663  1.00  0.00           O  
HETATM    9  O5  UNL     1       2.746  -0.669  -0.162  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.062  -2.092  -0.224  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.625   1.463  -0.636  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.870   1.615   1.161  1.00  0.00           H  
HETATM   13  H4  UNL     1       3.660  -0.346  -0.428  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5   11   12
CONECT    5    6    6    7
CONECT    7    8    8    9
CONECT    9   13
END
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SMILES for HMDB0000223 (Oxalacetic acid)

OC(=O)CC(=O)C(O)=O
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INCHI for HMDB0000223 (Oxalacetic acid)

InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC4H4O5
Average Molecular Weight132.0716
Monoisotopic Molecular Weight132.005873238
IUPAC Name2-oxobutanedioic acid
Traditional Nameoxalacetate
CAS Registry Number328-42-7
SMILES
OC(=O)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
InChI KeyKHPXUQMNIQBQEV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point161 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility134 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available139.446http://allccs.zhulab.cn/database/detail?ID=AllCCS00001954
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Liver
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified2 uMAdult (>18 years old)BothAnoxia details
Associated Disorders and Diseases
Disease References
Anoxia
  1. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031075
KNApSAcK IDC00001197
Chemspider ID945
KEGG Compound IDC00036
BioCyc IDOXALACETIC_ACID
BiGG ID33604
Wikipedia LinkOxaloacetic_acid
METLIN ID123
PubChem Compound970
PDB IDNot Available
ChEBI ID30744
Food Biomarker OntologyNot Available
VMH IDOAA
MarkerDB IDMDB00000105
Good Scents IDNot Available
References
Synthesis ReferenceHeidelberger, Charles; Hurlbert, Robert B. The synthesis of oxalacetic acid-I-C14 and orotic acid-6-C14. Journal of the American Chemical Society (1950), 72 4704-6.
Material Safety Data Sheet (MSDS)Not Available
General References

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. ATP-citrate synthase
General function:
Involved in ATP citrate synthase activity
Specific function:
ATP citrate-lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Has a central role in de novo lipid synthesis. In nervous tissue it may be involved in the biosynthesis of acetylcholine.
Gene Name:
ACLY
Uniprot ID:
P53396
Molecular weight:
120838.27
Reactions
ADP + Phosphate + Acetyl-CoA + Oxalacetic acid → Adenosine triphosphate + Citric acid + Coenzyme Adetails
Adenosine triphosphate + Citric acid + Coenzyme A → ADP + Phosphate + Acetyl-CoA + Oxalacetic aciddetails
Enzyme Details
2. Pyruvate carboxylase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
Gene Name:
PC
Uniprot ID:
P11498
Molecular weight:
129632.565
Reactions
Adenosine triphosphate + Pyruvic acid + Hydrogen carbonate → ADP + Phosphate + Oxalacetic aciddetails
Enzyme Details
3. Citrate synthase, mitochondrial
General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Not Available
Gene Name:
CS
Uniprot ID:
O75390
Molecular weight:
51712.025
Reactions
Acetyl-CoA + Water + Oxalacetic acid → Citric acid + Coenzyme Adetails
Citric acid + Coenzyme A → Acetyl-CoA + Water + Oxalacetic aciddetails
Enzyme Details
4. D-aspartate oxidase
General function:
Involved in D-amino-acid oxidase activity
Specific function:
Selectively catalyzes the oxidative deamination of D-aspartate and its N-methylated derivative, N-methyl D-aspartate.
Gene Name:
DDO
Uniprot ID:
Q99489
Molecular weight:
40992.53
Reactions
D-Aspartic acid + Water + Oxygen → Oxalacetic acid + Ammonia + Hydrogen peroxidedetails
Enzyme Details
5. Aspartate aminotransferase, cytoplasmic
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
Reactions
L-Aspartic acid + Oxoglutaric acid → Oxalacetic acid + Glutamic aciddetails
Enzyme Details
6. Aspartate aminotransferase, mitochondrial
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
L-Aspartic acid + Oxoglutaric acid → Oxalacetic acid + Glutamic aciddetails
Enzyme Details
7. NADP-dependent malic enzyme
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME1
Uniprot ID:
P48163
Molecular weight:
64149.075
Reactions
Oxalacetic acid → Pyruvic acid + CO(2)details
Enzyme Details
8. Malate dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
MDH2
Uniprot ID:
P40926
Molecular weight:
35502.935
Reactions
Malic acid + NAD → Oxalacetic acid + NADHdetails
Malic acid + NAD → Oxalacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
9. NADP-dependent malic enzyme, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME3
Uniprot ID:
Q16798
Molecular weight:
67067.875
Reactions
Oxalacetic acid → Pyruvic acid + CO(2)details
Enzyme Details
10. Malate dehydrogenase, cytoplasmic
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
MDH1
Uniprot ID:
P40925
Molecular weight:
38627.255
Reactions
Malic acid + NAD → Oxalacetic acid + NADHdetails
Malic acid + NAD → Oxalacetic acid + NADH + Hydrogen Iondetails

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters