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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:09 UTC
Update Date2021-09-14 15:45:36 UTC
HMDB IDHMDB0012156
Secondary Accession Numbers
  • HMDB12156
Metabolite Identification
Common Name3-Isopropylmalic acid
Description3-Isopropylmalic acid (CAS: 16048-89-8) is an intermediate in valine, leucine, and isoleucine biosynthesis. It is a substrate for 3-isopropylmalate dehydrogenase (TT_C0867) and can be generated from the reduction of 2-isopropyl-3-oxosuccinate. Leucine biosynthesis involves a five-step conversion process starting with the valine precursor 2-keto-isovalerate. The final step in this pathway is catalyzed by two transaminases of broad specificity: branched-chain amino acid transferase (IlvE) and tyrosine aminotransferase (TyrB). This pathway is part of the super pathway of leucine, valine, and isoleucine biosynthesis that generates not only isoleucine and valine but also leucine.
Structure
Data?1586461194
Synonyms
ValueSource
(2R,3S)-2-Hydroxy-3-isopropylsuccinic acidChEBI
(2R,3S)-3-Carboxy-2-hydroxy-4-methylpentanoic acidChEBI
2-D-Threo-hydroxy-3-carboxy-isocaproateChEBI
2-D-Threo-hydroxy-3-carboxyisocaproic acidChEBI
3-Carboxy-2-hydroxy-4-methylpentanoateChEBI
3-IsopropylmalateChEBI
(2R,3S)-2-Hydroxy-3-isopropylsuccinateGenerator
(2R,3S)-3-Carboxy-2-hydroxy-4-methylpentanoateGenerator
2-D-Threo-hydroxy-3-carboxy-isocaproic acidGenerator
2-D-Threo-hydroxy-3-carboxyisocaproateGenerator
3-Carboxy-2-hydroxy-4-methylpentanoic acidGenerator
3-Isopropylmalic acidGenerator
(2R,3S)-2-Hydroxy-3-(propan-2-yl)butanedioateHMDB
(2R,3S)-2-Hydroxy-3-(propan-2-yl)butanedioic acidHMDB
(2R,3S)-3-IsopropylmalateHMDB
(2R,3S)-3-Isopropylmalic acidHMDB
3-3-Isopropylmalic acidHMDB
IPMHMDB
beta-Isopropylmalate, erythro-(L)-isomerMeSH, HMDB
beta-IsopropylmalateMeSH, HMDB
(2R,3S)-2-Hydroxy-3-(1-methylethyl)butanedioic acidHMDB
2-Hydroxy-3-(1-methylethyl)butanedioic acidHMDB
IsopropylmalateHMDB
Isopropylmalic acidHMDB
beta-Isopropylmalic acidHMDB
β-Isopropylmalic acidHMDB
Chemical FormulaC7H12O5
Average Molecular Weight176.1672
Monoisotopic Molecular Weight176.068473494
IUPAC Name(2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid
Traditional Name(2R,3S)-3-isopropylmalic acid
CAS Registry Number126576-14-5
SMILES
CC(C)[C@@H]([C@@H](O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H12O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-5,8H,1-2H3,(H,9,10)(H,11,12)/t4-,5+/m0/s1
InChI KeyRNQHMTFBUSSBJQ-CRCLSJGQSA-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
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot 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]-Not Available127.46http://allccs.zhulab.cn/database/detail?ID=AllCCS00000279
Predicted Molecular Properties
PropertyValueSource
Water Solubility83.3 g/LALOGPS
logP10(0.28) g/LALOGPS
logP10(0.16) g/LChemAxon
logS10(-0.33) g/LALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.6 m³·mol⁻¹ChemAxon
Polarizability16.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.29731661259
DarkChem[M-H]-138.65731661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Isopropylmalic acidCC(C)[C@@H]([C@@H](O)C(O)=O)C(O)=O2485.1Standard polar33892256
3-Isopropylmalic acidCC(C)[C@@H]([C@@H](O)C(O)=O)C(O)=O1292.8Standard non polar33892256
3-Isopropylmalic acidCC(C)[C@@H]([C@@H](O)C(O)=O)C(O)=O1529.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Isopropylmalic acid,1TMS,isomer #1CC(C)[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)C(=O)O1435.7Semi standard non polar33892256
3-Isopropylmalic acid,1TMS,isomer #2CC(C)[C@H](C(=O)O)[C@@H](O)C(=O)O[Si](C)(C)C1427.1Semi standard non polar33892256
3-Isopropylmalic acid,1TMS,isomer #3CC(C)[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)C(=O)O1423.6Semi standard non polar33892256
3-Isopropylmalic acid,2TMS,isomer #1CC(C)[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O1504.6Semi standard non polar33892256
3-Isopropylmalic acid,2TMS,isomer #2CC(C)[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1487.1Semi standard non polar33892256
3-Isopropylmalic acid,2TMS,isomer #3CC(C)[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C1511.1Semi standard non polar33892256
3-Isopropylmalic acid,3TMS,isomer #1CC(C)[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1592.1Semi standard non polar33892256
3-Isopropylmalic acid,1TBDMS,isomer #1CC(C)[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O1678.4Semi standard non polar33892256
3-Isopropylmalic acid,1TBDMS,isomer #2CC(C)[C@H](C(=O)O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C1672.0Semi standard non polar33892256
3-Isopropylmalic acid,1TBDMS,isomer #3CC(C)[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O1668.2Semi standard non polar33892256
3-Isopropylmalic acid,2TBDMS,isomer #1CC(C)[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O1954.6Semi standard non polar33892256
3-Isopropylmalic acid,2TBDMS,isomer #2CC(C)[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1937.0Semi standard non polar33892256
3-Isopropylmalic acid,2TBDMS,isomer #3CC(C)[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C1948.5Semi standard non polar33892256
3-Isopropylmalic acid,3TBDMS,isomer #1CC(C)[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2193.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Isopropylmalic acid GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-4ec856cc4eb69ab95ccc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Isopropylmalic acid GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-4ec856cc4eb69ab95ccc2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Isopropylmalic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-a5c729805d94db1fb7b32016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Isopropylmalic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00bl-9135000000-1982df651c1931669dae2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Isopropylmalic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 10V, Positive-QTOFsplash10-0a7i-1900000000-224a91a676e183e743332015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 20V, Positive-QTOFsplash10-06sl-7900000000-b06817c1e6edcae6d4252015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 40V, Positive-QTOFsplash10-052o-9300000000-479bb2145817abc0bf1a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 10V, Negative-QTOFsplash10-0059-1900000000-acde792ba60cae65a2162015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 20V, Negative-QTOFsplash10-0far-9700000000-cf8f9dd2b32cfd503f422015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 40V, Negative-QTOFsplash10-0a59-9100000000-138111afc561c6d0a2ec2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 10V, Positive-QTOFsplash10-03ei-3900000000-99922dc6120c0bc9d5ac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 20V, Positive-QTOFsplash10-000i-9300000000-6c8d0a906ce3776c47692021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 40V, Positive-QTOFsplash10-052f-9000000000-229b51add43b0209aa102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 10V, Negative-QTOFsplash10-001i-1900000000-bcc925b37cd5d5f31b5a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 20V, Negative-QTOFsplash10-01q0-7900000000-222a48c445cf7526d6e62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Isopropylmalic acid 40V, Negative-QTOFsplash10-0019-9100000000-6003ddbcaf34c522b89a2021-09-24Wishart 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
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028813
KNApSAcK IDC00019691
Chemspider ID4575349
KEGG Compound IDC04411
BioCyc ID2-D-THREO-HYDROXY-3-CARBOXY-ISOCAPROATE
BiGG IDNot Available
Wikipedia LinkIsopropylmalic acid
METLIN IDNot Available
PubChem Compound5462261
PDB IDIPM
ChEBI ID43468
Food Biomarker OntologyNot Available
VMH ID3C2HMP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.