General Information of MET (ID: META00256)
Name Adipic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1,4-Butanedicarboxylate; 1,4-Butanedicarboxylic acid; 1,6-Hexanedioate; 1,6-Hexanedioic acid; Acifloctin; Acinetten; Adi-pure; Adilactetten; Adipate; Adipic acid, MG salt (1:1); Adipic acid, calcium salt; Adipic acid, cu salt; Adipic acid, cu(+2) salt; Adipic acid, cu(+2) salt (1:1); Adipic acid, diammonium salt; Adipic acid, disodium salt; Adipic acid, monoammonium salt; Adipic acid, nickel salt; Adipic acid, potassium salt; Adipic acid, sodium salt; Adipinate; Adipinic acid; Adipinsaeure; Ammonium adipate; Diammonium adipate; Hexan-1,6-dicarboxylate; Hexan-1,6-dicarboxylic acid; Hexanedioate; Hexanedioic acid; INS no. 355; Kyselina adipova; Magnesium adipate; Molten adipate; Molten adipic acid; Sodium adipate; e 355; e-355; e355
Source Endogenous;Drug Metabolite;Fatty acyls;Food;Cosmetic;Food additives
Structure Type   Fatty acids and conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Fatty acids and conjugates
PubChem CID
196
HMDB ID
HMDB0000448
Formula
C6H10O4
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
C06104
ChEBI ID
30832
FooDB ID
FDB008309
ChemSpider ID
191
METLIN ID
115
Physicochemical Properties Molecular Weight 146.14 Topological Polar Surface Area 74.6
XlogP 0.1 Complexity 114
Heavy Atom Count 10 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Function
Adipic acid is an important inudstrial dicarboxylic acid with about 2.5 billion kilograms produced per year. It is used mainly in the production of nylon. It occurs relatively rarely in nature. It has a tart taste and is also used as an additive and gelling agent in jello or gelatins. It is also used in some calcium carbonate antacids to make them tart. Adipic acid has also been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. Adipic acid in the urine and in the blood is typically exogenous in origin and is a good biomarker of jello consumption. In fact, a condition known as adipic aciduria is actually an artifact of jello consumption. However, certain disorders (such as diabetes and glutaric aciduria type I.) can lead to elevated levels of adipic acid snd other dicarboxcylic acids (such as suberic acid) in urine. Moreover, adipic acid is also found to be associated with 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, carnitine-acylcarnitine translocase deficiency, malonyl-Coa decarboxylase deficiency, and medium Chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism. Adipic acid is also microbial metabolite found in Escherichia.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      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 [1]
                      Introduced Variation Mutation (patients: c.454dup (p.Thr152Asnfs*39)) of GRHPR
                      Induced Change Adipic 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 adipic acid levels compared with control group.
      Transcription factor (TF)
            R2R3-MYB (AN2) 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 Overexpression of AN2
                      Induced Change Adipic acid concentration: decrease (FC = 0.21)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the decrease of adipic acid levels compared with control group.
      Transferases (EC 2)
            Succinate-hydroxymethylglutarate CoA-transferase (SUGCT) 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 Sugct
                      Induced Change Adipic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Diabetes mellitus [ICD-11: 5A14]
                      Details It is reported that knockout of Sugct leads to the increase of adipic acid levels compared with control group.
References
1 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.
2 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.
3 Knockout of the non-essential gene SUGCT creates diet-linked, age-related microbiome disbalance with a diabetes-like metabolic syndrome phenotype. Cell Mol Life Sci. 2020 Sep;77(17):3423-3439.

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