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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:47 UTC
HMDB IDHMDB0000402
Secondary Accession Numbers
  • HMDB00402
Metabolite Identification
Common Name2-Isopropylmalic acid
Description2-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 (PMID: 2338430 , 544608 ), and in hemofiltrates (PMID: 7251751 ). 2-Isopropylmalic acid is elevated during fasting and diabetic ketoacidosis (PMID: 1591279 ). It is also a metabolite found in Acetobacter (PMID: 6035258 ).
Structure
Thumb
Synonyms
Chemical FormulaC7H12O5
Average Molecular Weight176.1672
Monoisotopic Molecular Weight176.068473494
IUPAC Name(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid
Traditional Name2-isopropyl-malic acid
CAS Registry Number49601-06-1
SMILES
CC(C)[C@@](O)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t7-/m0/s1
InChI KeyBITYXLXUCSKTJS-ZETCQYMHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Tertiary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point144 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg128.12230932474
[M-H]-Not Available128.122http://allccs.zhulab.cn/database/detail?ID=AllCCS00000191
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011983
KNApSAcK IDC00019690
Chemspider ID4444155
KEGG Compound IDC02504
BioCyc ID3-CARBOXY-3-HYDROXY-ISOCAPROATE
BiGG IDNot Available
Wikipedia LinkIsopropylmalic acid
METLIN ID339
PubChem Compound5280523
PDB IDNot Available
ChEBI ID35128
Food Biomarker OntologyNot Available
VMH ID3C3HMP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSchloss J V; Magolda R; Emptage M Synthesis of alpha-isopropylmalate, beta-isopropylmalate, and dimethylcitraconate. Methods in enzymology (1988), 166 92-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Spiteller M, Spiteller G: [Occurrence of alpha-alkyl-substituted malic acids, and beta-hydroxy-beta-alkyl-substituted dicarboxylic and tricarboxylic acid derivatives in normal urine (author's transl)]. J Chromatogr. 1979 Nov 11;164(3):319-29. [PubMed:544608 ]
  2. Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [PubMed:2338430 ]
  3. Verhaeghe BJ, Van Bocxlaer JF, De Leenheer AP: Gas chromatographic/mass spectrometric identification of 3-hydroxydicarboxylic acids in urine. Biol Mass Spectrom. 1992 Jan;21(1):27-32. [PubMed:1591279 ]
  4. Pinkston D, Spiteller G, Von Henning H, Matthaei D: High resolution gas chromatography mass spectrometry of the methyl esters of organic acids from uremic hemofiltrates. J Chromatogr. 1981 Apr 10;223(1):1-19. [PubMed:7251751 ]
  5. Maragoudakis ME, Strassman M: Biosynthesis of alpha-isopropylmalic and citric acids in Acetobacter suboxydans. J Bacteriol. 1967 Sep;94(3):512-6. [PubMed:6035258 ]