Details of Metabolite

General Information of MET (ID: META00484)
Name Oxalic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Acid, oxalic; Aluminum oxalate; Ammonium oxalate; Chromium (2+) oxalate; Chromium (3+) oxalate (3:2); Chromium oxalate; Diammonium oxalate; Dilithium oxalate; Dipotassium oxalate; Disodium oxalate; Ethandisaeure; Ethane-1,2-dioate; Ethane-1,2-dioic acid; Ethanedioate; Ethanedioic acid; Ethanedioic acid dihydrate; Ethanedionate; Ethanedionic acid; Ferric oxalate; H2Ox; HOOCCOOH; Iron (2+) oxalate (1:1); Iron (3+) oxalate; Iron oxalate; Kyselina stavelova; Magnesium oxalate; Magnesium oxalate (1:1); Manganese (2+) oxalate (1:1); Monoammonium oxalate; Monohydrogen monopotassium oxalate; Monopotassium oxalate; Monosodium oxalate; Oxaalzuur; Oxalate; Oxalate, aluminum; Oxalate, chromium; Oxalate, diammonium; Oxalate, dilithium; Oxalate, dipotassium; Oxalate, disodium; Oxalate, ferric; Oxalate, iron; Oxalate, magnesium; Oxalate, monoammonium; Oxalate, monohydrogen monopotassium; Oxalate, monopotassium; Oxalate, monosodium; Oxalate, potassium; Oxalate, potassium chromium; Oxalate, sodium; Oxalic acid; Oxalic acid 2-hydrate; Oxalic acid anhydrous; Oxalic acid diammonium salt; Oxalic acid dihydrate; Oxalsaeure; Potassium chromium oxalate; Potassium oxalate; Potassium oxalate (2:1); Sodium oxalate
Source Endogenous;Drug Metabolite;Drug;Escherichia Coli Metabolite;Food;Drug;Toxins/Pollutant;Cosmetic;TCM Ingredients;Plant Metabolite; Microbial
Structure Type   Dicarboxylic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Dicarboxylic acids and derivatives
PubChem CID
971
HMDB ID
HMDB0002329
Formula
C2H2O4
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00209
DrugBank ID
DB03902
ChEBI ID
16995
FooDB ID
FDB003357
ChemSpider ID
946
METLIN ID
113
Physicochemical Properties Molecular Weight 90.03 Topological Polar Surface Area 74.6
XlogP -0.3 Complexity 71.5
Heavy Atom Count 6 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Function
Oxalic acid is a strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent (Pubchem). Oxalic acid (IUPAC name: ethanedioic acid, formula H2C2O4) is a dicarboxylic acid with structure (HOOC)-(COOH). Because of the joining of two carboxyl groups, this is one of the strongest organic acids. It is also a reducing agent. The anions of oxalic acid as well as its salts and esters are known as oxalates. Bodily oxalic acid may also be synthesized via the metabolism of either glyoxylic acid or unused ascorbic acid (vitamin C), which is a serious health consideration for long term megadosers of vitamin C supplements. 80% of kidney stones are formed from calcium oxalate. Some Aspergillus species produce oxalic acid, which reacts with blood or tissue calcium to precipitate calcium oxalate. There is some preliminary evidence that the administration of probiotics can affect oxalic acid excretion rates (and presumably oxalic acid levels as well). Oxalic acid is found to be associated with fumarase deficiency and primary hyperoxaluria I, which are inborn errors of metabolism. Oxalic acid is a marker for yeast overgrowth from Aspergillus, Penicillum and/or Candida. Can also be elevated due to exposures from vitamin C or ethylene glycol poisoning. Oxalate is elevated in the urine of children with autism. Oxalic acid has also been identified as a uremic toxin according to the European Uremic Toxin Working Group.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Lyases (EC 4)
            Dihydrodipicolinate synthase-like (DHDPSL) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Mutation (patients: bi-allelic mutations) of HOGA1
                      Induced Change Oxalic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Carbohydrate metabolism disorders [ICD-11: 5C51]
                      Details It is reported that mutation (patients with bi-allelic mutations) of HOGA1 leads to the increase of oxalic acid levels compared with control group.
      Oxidoreductases (EC 1)
            Glyoxylate reductase/hydroxypyruvate reductase (GRHPR) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Mutation (patients: c.454dup (p.Thr152Asnfs*39)) of GRHPR
                      Induced Change Oxalic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Carbohydrate metabolism disorders [ICD-11: 5C51]
                      Details It is reported that mutation (patients with c.454dup (p.Thr152Asnfs*39)) of GRHPR leads to the increase of oxalic acid levels compared with control group.
      Sulfate permease (SULP)
            Solute carrier family 26 member 1 (SLC26A1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Overexpression of SLC26A1
                      Induced Change Oxalic acid concentration: increase (FC = 6)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC26A1 leads to the increase of oxalic acid levels compared with control group.
            Solute carrier family 26 member 6 (SLC26A6) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Knockdown (siRNA) of SLC26A6
                      Induced Change Oxalic acid concentration: decrease (FC = 0.60)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockdown of SLC26A6 leads to the decrease of oxalic acid levels compared with control group.
      Transferases (EC 2)
            Deacetylase sirtuin-5 (SIRT5) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [5]
                      Introduced Variation Knockout of Sirt5
                      Induced Change Oxalic acid concentration: increase (FC = 1.34)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Sirt5 leads to the increase of oxalic acid levels compared with control group.
References
1 Primary hyperoxaluria type III--a model for studying perturbations in glyoxylate metabolism. J Mol Med (Berl). 2012 Dec;90(12):1497-504.
2 Severe child form of primary hyperoxaluria type 2 - a case report revealing consequence of GRHPR deficiency on metabolism. BMC Med Genet. 2017 May 31;18(1):59.
3 Characterization of the human sulfate anion transporter (hsat-1) protein and gene (SAT1; SLC26A1). DNA Cell Biol. 2003 Feb;22(2):107-17.
4 Parsing apical oxalate exchange in Caco-2BBe1 monolayers: siRNA knockdown of SLC26A6 reveals the role and properties of PAT-1. Am J Physiol Gastrointest Liver Physiol. 2009 Nov;297(5):G918-29.
5 Metabolomics Based Identification of SIRT5 and Protein Kinase C Epsilon Regulated Pathways in Brain. Front Neurosci. 2018 Jan 30;12:32.

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