Details of Metabolite

General Information of MET (ID: META00148)
Name cis-Aconitic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(1Z)-1-Propene-1,2,3-tricarboxylate; (1Z)-1-Propene-1,2,3-tricarboxylic acid; (Z)-1-Propene-1,2,3-tricarboxylate; (Z)-1-Propene-1,2,3-tricarboxylic acid; (Z)-Aconitate; (Z)-Aconitic acid; 1-Propene-1,2,3-tricarboxylate; 1-Propene-1,2,3-tricarboxylic acid; 1-cis-2,3-Propenetricarboxylate; 1-cis-2,3-Propenetricarboxylic acid; Achilleic acid; Acid, achilleic; Acid, aconitic; Acid, acontic; Acid, adonic; Acid, carboxyglutaconic; Acid, citridic; Acid, citridinic; Acid, equisetic; Acid, pyrocitric; Aconitate; Aconitic acid; Acontic acid; Adonic acid; Carboxyglutaconic acid; Citridic acid; Citridinic acid; Equisetic acid; Pyrocitric acid; cis-1-Propene-1,2,3-tricarboxylate; cis-1-Propene-1,2,3-tricarboxylic acid; cis-Aconate; cis-Aconic acid; cis-Aconitate; cis-Oxaloacetate; cis-Oxaloacetic acid
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food additives;TCM Ingredients;Microbial
Structure Type   Tricarboxylic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Tricarboxylic acids and derivatives
PubChem CID
643757
HMDB ID
HMDB0000072
Formula
C6H6O6
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
C00417
ChEBI ID
32805
FooDB ID
FDB008306
ChemSpider ID
558863
METLIN ID
5130
Physicochemical Properties Molecular Weight 174.11 Topological Polar Surface Area 112
XlogP -1 Complexity 251
Heavy Atom Count 12 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Function
cis-Aconitic acid is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid. The enzyme aconitase (aconitate hydratase; EC 4.2.1.3) catalyses the stereo-specific isomerization of citrate to isocitrate via cis-aconitate in the tricarboxylic acid cycle.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      GPCR rhodopsin (GPCR-1)
            Adrenergic receptor beta-3 (ADRB3) 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 Agonist (CL-316,243) of Adrb3
                      Induced Change cis-Aconitic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that agonist of ADRB3 leads to the increase of cis-aconitic acid levels compared with control group.
      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 cis-Aconitic 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 cis-aconitic acid levels compared with control group.
      Oxidoreductases (EC 1)
            Formyltetrahydrofolate dehydrogenase (ALDH1L2) 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 Mutation of ALDH1L2
                      Induced Change cis-Aconitic acid concentration: increase (FC = 3.57)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Genetic disorders of keratinisation [ICD-11: EC20]
                      Details It is reported that mutation (patients) of ALDH1L2 leads to the increase of cis-aconitic 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 [4]
                      Introduced Variation Knockout of TP53
                      Induced Change cis-Aconitic acid concentration: increase (Log2 FC=1.18)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of cis-aconitic acid levels compared with control group.
      Transcription factor (TF)
            Myc proto-oncogene protein (MYC) 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 Knockdown (siRNA) of MYC
                      Induced Change cis-Aconitic acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colorectal cancer [ICD-11: 2B91]
                      Details It is reported that knockdown of MYC leads to the decrease of cis-aconitic 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 [6]
                      Introduced Variation Knockout of Sirt5
                      Induced Change cis-Aconitic acid concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Sirt5 leads to the decrease of cis-aconitic acid levels compared with control group.
References
1 Metabolic changes in adipose tissues in response to 3 -adrenergic receptor activation in mice. J Cell Biochem. 2019 Jan;120(1):821-835.
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 Deleterious mutations in ALDH1L2 suggest a novel cause for neuro-ichthyotic syndrome. NPJ Genom Med. 2019 Jul 23;4:17.
4 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.
5 Global metabolic reprogramming of colorectal cancer occurs at adenoma stage and is induced by MYC. Proc Natl Acad Sci U S A. 2017 Sep 12;114(37):E7697-E7706.
6 HNF4 Regulates Fatty Acid Oxidation and Is Required for Renewal of Intestinal Stem Cells in Mice. Gastroenterology. 2020 Mar;158(4):985-999.e9.

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