Details of Metabolite

General Information of MET (ID: META00301)
Name Malonic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Carboxyacetic acid; Dicarboxylate; Dicarboxylic acid; Dicarboxymethane; Dithallium malonate; H2Malo; HOOC-CH2-COOH; Kyselina malonova; Malonate; Malonate dicarboxylic acid; Malonic acid; Malonic acid, 1,3-(14)C2-labeled; Malonic acid, 2-(14)C-labeled; Malonic acid, diammonium salt; Malonic acid, dipotassium salt; Malonic acid, disodium salt; Malonic acid, disodium salt, 1-(14)C-labeled; Malonic acid, dithallium salt; Malonic acid, monocalcium salt; Malonic acid, monosodium salt; Malonic acid, potassium salt; Malonic acid, sodium salt; Metahnedicarboxylic acid; Methanedicarbonic acid; Methanedicarboxylic acid; Monosodium malonate; Propanedioate; Propanedioic acid; Propanedioic acid dithallium salt; Propanediolic acid; Thallium malonate; Thallous malonate; alpha,Omega-dicarboxylic acid
Source Endogenous;Drug Metabolite;Yeast Metabolite;Fatty acyls;Food;Drug;Cosmetic;TCM Ingredients;Pharmaceutical additive; 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
867
HMDB ID
HMDB0000691
Formula
C3H4O4
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
C04025
DrugBank ID
DB02175
ChEBI ID
30794
FooDB ID
FDB008117
ChemSpider ID
844
METLIN ID
3237
Physicochemical Properties Molecular Weight 104.06 Topological Polar Surface Area 74.6
XlogP -0.8 Complexity 83.1
Heavy Atom Count 7 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Function
Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionised form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's ethyl ester. The name originates from Latin malum, meaning apple. Malonic acid is the archetypal example of a competitive inhibitor: it acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain. Malonic acid is found to be associated with malonyl-CoA decarboxylase deficiency, which is an inborn error of metabolism.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Apolipoprotein (Apo)
            Apolipoprotein A-II (APOA2) 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 (-265T >C(rs5082)) of APOA2
                      Induced Change Malonic acid concentration: decrease (FC = 0.83)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that mutation (-265T >C(rs5082)) of APOA2 leads to the decrease of malonic acid levels compared with control group.
References
1 Epigenomics and metabolomics reveal the mechanism of the APOA2-saturated fat intake interaction affecting obesity. Am J Clin Nutr. 2018 Jul 1;108(1):188-200.

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