Details of Metabolite

General Information of MET (ID: META00068)
Name Maleic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2Z)-2-Butenedioate; (2Z)-2-Butenedioic acid; (2Z)-But-2-enedioate; (2Z)-But-2-enedioic acid; (2Z)-Butene-2-dioate; (2Z)-Butene-2-dioic acid; (Z)-2-Butenedioate; (Z)-2-Butenedioic acid; (Z)-Butenedioate; (Z)-Butenedioic acid; 2-Butenedioate; 2-Butenedioic acid; H2Male; Hydrogen maleate; Kyselina maleinova; MAE; Maleate; Maleic acid, ammonium salt; Maleic acid, calcium salt; Maleic acid, dipotassium salt; Maleic acid, disodium salt; Maleic acid, iron salt; Maleic acid, monoammonium salt; Maleic acid, monocopper (2+) salt; Maleic acid, monosodium salt; Maleic acid, neodymium salt; Maleic acid, potassium salt; Maleic acid, sodium salt; Maleinic acid; Malenic acid; Malezid CM; Scotchbond multipurpose etchant; Sodium maleate; Toxilate; Toxilic acid; cis-1,2-Ethylenedicarboxylate; cis-1,2-Ethylenedicarboxylic acid; cis-2-Butenedioate; cis-2-Butenedioic acid; cis-But-2-enedioate; cis-But-2-enedioic acid; cis-Butenedioate; cis-Butenedioic acid
Source Endogenous;Food;Toxins/Pollutant;Cosmetic;TCM Ingredients;Pharmaceutical additive
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
444266
HMDB ID
HMDB0000176
Formula
C4H4O4
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
C01384
DrugBank ID
DB04299
ChEBI ID
18300
FooDB ID
FDB008113
Physicochemical Properties Molecular Weight 116.07 Topological Polar Surface Area 74.6
XlogP -0.3 Complexity 119
Heavy Atom Count 8 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Function
Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      GPCR rhodopsin (GPCR-1)
            Succinate receptor (SUCNR1) 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 Maleic acid addition (1 hours)
                      Induced Change SUCNR1 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that maleic acid addition causes the increase of SUCNR1 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Leukotriene-C4 hydrolase (GGT1) 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 Knockdown (siRNA) of GGT1
                      Induced Change Maleic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Renal cell carcinoma [ICD-11: 2C90]
                      Details It is reported that knockdown of GGT1 leads to the increase of maleic acid levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) 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 Knockout of TP53
                      Induced Change Maleic acid concentration: decrease (Log2 FC=0.86)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of maleic acid levels compared with control group.
References
1 Identification and pharmacological characterization of succinate receptor agonists. Br J Pharmacol. 2017 May;174(9):796-808.
2 Impairment of gamma-glutamyl transferase 1 activity in the metabolic pathogenesis of chromophobe renal cell carcinoma. Proc Natl Acad Sci U S A. 2018 Jul 3;115(27):E6274-E6282.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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