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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:45:28 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
Data?1583424160
Synonyms
ValueSource
(2S)-2-Hydroxy-2-isopropylsuccinic acidChEBI
(2S)-2-IsopropylmalateChEBI
(3S)-3-Carboxy-3-hydroxy-4-methylpentanoic acidChEBI
(3S)-3-Carboxy-3-hydroxyisocaproic acidChEBI
(S)-2-Hydroxy-2-(isopropyl)succinic acidChEBI
3-Carboxy-3-hydroxy-4-methylpentanoateChEBI
3-Carboxy-3-hydroxyisocaproateChEBI
(2S)-2-Hydroxy-2-isopropylsuccinateGenerator
(2S)-2-Isopropylmalic acidGenerator
(3S)-3-Carboxy-3-hydroxy-4-methylpentanoateGenerator
(3S)-3-Carboxy-3-hydroxyisocaproateGenerator
(S)-2-Hydroxy-2-(isopropyl)succinateGenerator
3-Carboxy-3-hydroxy-4-methylpentanoic acidGenerator
3-Carboxy-3-hydroxyisocaproic acidGenerator
2-IsopropylmalateGenerator
2-Hydroxy-2-isopropylsuccinateHMDB
2-Hydroxy-2-isopropylsuccinic acidHMDB
2-Isopropyl-2-hydroxybutanedioateHMDB
2-Isopropyl-2-hydroxybutanedioic acidHMDB
2-Isopropyl-malic acidHMDB
a-IsopropylmalateHMDB
a-Isopropylmalic acidHMDB
alpha-IsopropylmalateHMDB
alpha-Isopropylmalic acidHMDB
(2S)-2-Hydroxy-2-(1-methylethyl)butanedioic acidHMDB
(2S)-2-Hydroxy-2-(propan-2-yl)butanedioic acidHMDB
(S)-(+)-2-Isopropylmalic acidHMDB
2-Hydroxy-2-(1-methylethyl)butanedioic acidHMDB
Α-isopropylmalateHMDB
Α-isopropylmalic acidHMDB
2-Isopropylmalic acidHMDB
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point144 - 146 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M-H]-MetCCS_train_neg128.12230932474
AllCCS[M-H]-Not Available128.122http://allccs.zhulab.cn/database/detail?ID=AllCCS00000191
Predicted Molecular Properties
PropertyValueSource
Water Solubility181 g/LALOGPS
logP10(-0.29) g/LALOGPS
logP10(0.21) g/LChemAxon
logS10(0.01) g/LALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.58 m³·mol⁻¹ChemAxon
Polarizability16.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.70631661259
DarkChem[M-H]-132.65831661259
AllCCS[M+H]+139.39532859911
AllCCS[M-H]-134.54132859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Isopropylmalic acid,1TMS,#1CC(C)[C@](CC(=O)O)(O[Si](C)(C)C)C(=O)O1510.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,1TMS,#2CC(C)[C@@](O)(CC(=O)O[Si](C)(C)C)C(=O)O1483.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,1TMS,#3CC(C)[C@@](O)(CC(=O)O)C(=O)O[Si](C)(C)C1448.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,2TMS,#1CC(C)[C@](CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O1548.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,2TMS,#2CC(C)[C@](CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1544.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,2TMS,#3CC(C)[C@@](O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1497.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,3TMS,#1CC(C)[C@](CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1595.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,1TBDMS,#1CC(C)[C@](CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O1743.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,1TBDMS,#2CC(C)[C@@](O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1726.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,1TBDMS,#3CC(C)[C@@](O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1722.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,2TBDMS,#1CC(C)[C@](CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O1994.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,2TBDMS,#2CC(C)[C@](CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1987.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,2TBDMS,#3CC(C)[C@@](O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1955.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Isopropylmalic acid,3TBDMS,#1CC(C)[C@](CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2225.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-1c869c73651e7e4e5dda2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00bl-9134000000-30fabfd0c26c38444fff2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropylmalic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-004i-0900000000-1bb48f5ddadbf88b8f6c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-00kr-9400000000-5df8f3f29d2e8a962cac2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-05n0-9200000000-c62b1543d0e6a41388f12012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Negative-QTOFsplash10-014r-6900000000-983e4a8edd0725d269792021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Negative-QTOFsplash10-016r-1900000000-5aa4d41c6ff31081d9d72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Positive-QTOFsplash10-00di-9200000000-d4b84f7b5f2a53ac58002021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Positive-QTOFsplash10-0006-9000000000-c680094e514a83eea9782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Negative-QTOFsplash10-052o-9000000000-365c84abb7ec259fb43e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Positive-QTOFsplash10-0006-9000000000-e28ea8cd657f96ff83572021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Positive-QTOFsplash10-0690-1900000000-3b83300261e0daab2ef12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Positive-QTOFsplash10-0006-9700000000-2652db028b01706ac0422016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Positive-QTOFsplash10-00di-9300000000-808bda4307e96bcfcc832016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Negative-QTOFsplash10-003r-2900000000-9fa33cd594a81b5d67cd2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Negative-QTOFsplash10-055r-9700000000-8ab90438d0e6c9b7d0be2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Negative-QTOFsplash10-0a4r-9100000000-41e1c40b755f8bfaf0002016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Positive-QTOFsplash10-01x9-9800000000-53afadde706df1ef69ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Positive-QTOFsplash10-0006-9000000000-4bfe3581b4b94540fea02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Positive-QTOFsplash10-0006-9000000000-1470f6a6a1859e4527122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 10V, Negative-QTOFsplash10-014i-2900000000-9a718ee22b675ce189802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 20V, Negative-QTOFsplash10-00kr-8900000000-188b5287c7dbbce2559f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropylmalic acid 40V, Negative-QTOFsplash10-000l-9000000000-2a93d25f081bcaa86a532021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.114 +/- 0.0493 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.159 +/- 0.0746 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.218 +/- 0.138 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.247 +/- 0.161 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
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)Download (PDF)
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 ]