Details of Metabolite

General Information of MET (ID: META00252)
Name 2-Isopropylmalic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S)-2-Hydroxy-2-(1-methylethyl)butanedioic acid; (2S)-2-Hydroxy-2-(propan-2-yl)butanedioic acid; (2S)-2-Hydroxy-2-isopropylsuccinate; (2S)-2-Hydroxy-2-isopropylsuccinic acid; (2S)-2-Isopropylmalate; (2S)-2-Isopropylmalic acid; (3S)-3-Carboxy-3-hydroxy-4-methylpentanoate; (3S)-3-Carboxy-3-hydroxy-4-methylpentanoic acid; (3S)-3-Carboxy-3-hydroxyisocaproate; (3S)-3-Carboxy-3-hydroxyisocaproic acid; (S)-(+)-2-Isopropylmalic acid; (S)-2-Hydroxy-2-(isopropyl)succinate; (S)-2-Hydroxy-2-(isopropyl)succinic acid; 2-Hydroxy-2-(1-methylethyl)butanedioic acid; 2-Hydroxy-2-isopropylsuccinate; 2-Hydroxy-2-isopropylsuccinic acid; 2-Isopropyl-2-hydroxybutanedioate; 2-Isopropyl-2-hydroxybutanedioic acid; 2-Isopropyl-malic acid; 2-Isopropylmalate; 3-Carboxy-3-hydroxy-4-methylpentanoate; 3-Carboxy-3-hydroxy-4-methylpentanoic acid; 3-Carboxy-3-hydroxyisocaproate; 3-Carboxy-3-hydroxyisocaproic acid; a-Isopropylmalate; a-Isopropylmalic acid; alpha-Isopropylmalate; alpha-Isopropylmalic acid
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Fatty acyls;Food;TCM Ingredients;Microbial
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
5280523
HMDB ID
HMDB0000402
Formula
C7H12O5
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
C02504
ChEBI ID
35128
FooDB ID
FDB030115
ChemSpider ID
4444155
METLIN ID
339
Physicochemical Properties Molecular Weight 176.17 Topological Polar Surface Area 94.8
XlogP -0.2 Complexity 198
Heavy Atom Count 12 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Function
2-Isopropylmalic acid (CAS: 3237-44-3), also known as 3-carboxy-3-hydroxyisocaproic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Isopropylmalic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Isopropylmalic acid is an alpha-hydroxy organic acid regularly occurring in the urine of healthy individuals , and in hemofiltrates. 2-Isopropylmalic acid is elevated during fasting and diabetic ketoacidosis. It is also a metabolite found in Acetobacter.
Regulatory Network
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 [1]
                      Introduced Variation Knockdown (siRNA) of GGT1
                      Induced Change 2-Isopropylmalic 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 2-isopropylmalic 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 2-Isopropylmalic acid concentration: decrease (FC = 0.23)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the decrease of 2-isopropylmalic acid levels compared with control group.
References
1 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.
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.

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