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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:36 UTC
Update Date2022-03-07 02:51:22 UTC
HMDB IDHMDB0012241
Secondary Accession Numbers
  • HMDB12241
Metabolite Identification
Common NameIsopropylmaleic acid
Description2-Isopropylmaleic acid belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually they are saturated and contain one or more methyl groups. However, branches other than methyl groups may be present. 2-Isopropylmaleic acid is a moderately acidic compound (based on its pKa). Isopropylmaleic acid is found in the leucine biosynthesis pathway. It is synthesized from oxoisovalerate by 2-isopropylmalate synthase and converted into isopropyl-3-oxosuccinate by 3-isopropylmalate dehydrogenase. The 2- and 3-isopropyl derivatives of isopropylmaleic acid are interconverted by the enzyme isopropylmalate dehydratase.
Structure
Data?1584110369
Synonyms
ValueSource
2-IsopropylmaleateChEBI
beta-IsopropylmaleateChEBI
2-Isopropylmaleic acidGenerator
b-IsopropylmaleateGenerator
b-Isopropylmaleic acidGenerator
beta-Isopropylmaleic acidGenerator
Β-isopropylmaleateGenerator
Β-isopropylmaleic acidGenerator
IsopropylmaleateGenerator
Isopropylmaleic acidGenerator
(2Z)-2-(1-Methylethyl)-2-butenedioic acidHMDB
Chemical FormulaC7H10O4
Average Molecular Weight158.1519
Monoisotopic Molecular Weight158.057908808
IUPAC Name(2Z)-2-(propan-2-yl)but-2-enedioic acid
Traditional Name2-isopropylmaleic acid
CAS Registry Number44976-69-4
SMILES
CC(C)C(=C\C(O)=O)\C(O)=O
InChI Identifier
InChI=1S/C7H10O4/c1-4(2)5(7(10)11)3-6(8)9/h3-4H,1-2H3,(H,8,9)(H,10,11)/b5-3-
InChI KeyNJMGRJLQRLFQQX-HYXAFXHYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.64 g/LALOGPS
logP1.05ALOGPS
logP1.09ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.11 m³·mol⁻¹ChemAxon
Polarizability15.11 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]+135.96831661259
DarkChem[M-H]-130.94731661259
DeepCCS[M+H]+132.63130932474
DeepCCS[M-H]-128.80230932474
DeepCCS[M-2H]-166.34830932474
DeepCCS[M+Na]+141.88830932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isopropylmaleic acid,1TMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C)C(=O)O1430.4Semi standard non polar33892256
Isopropylmaleic acid,1TMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C)C(=O)O1361.9Standard non polar33892256
Isopropylmaleic acid,1TMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C)C(=O)O1837.2Standard polar33892256
Isopropylmaleic acid,1TMS,isomer #2CC(C)/C(=C/C(=O)O)C(=O)O[Si](C)(C)C1432.4Semi standard non polar33892256
Isopropylmaleic acid,1TMS,isomer #2CC(C)/C(=C/C(=O)O)C(=O)O[Si](C)(C)C1331.2Standard non polar33892256
Isopropylmaleic acid,1TMS,isomer #2CC(C)/C(=C/C(=O)O)C(=O)O[Si](C)(C)C2016.4Standard polar33892256
Isopropylmaleic acid,2TMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1484.6Semi standard non polar33892256
Isopropylmaleic acid,2TMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1442.6Standard non polar33892256
Isopropylmaleic acid,2TMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1575.6Standard polar33892256
Isopropylmaleic acid,1TBDMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1676.1Semi standard non polar33892256
Isopropylmaleic acid,1TBDMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1572.9Standard non polar33892256
Isopropylmaleic acid,1TBDMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1969.4Standard polar33892256
Isopropylmaleic acid,1TBDMS,isomer #2CC(C)/C(=C/C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1680.6Semi standard non polar33892256
Isopropylmaleic acid,1TBDMS,isomer #2CC(C)/C(=C/C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1535.6Standard non polar33892256
Isopropylmaleic acid,1TBDMS,isomer #2CC(C)/C(=C/C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2043.5Standard polar33892256
Isopropylmaleic acid,2TBDMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1897.5Semi standard non polar33892256
Isopropylmaleic acid,2TBDMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1845.6Standard non polar33892256
Isopropylmaleic acid,2TBDMS,isomer #1CC(C)/C(=C/C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1884.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isopropylmaleic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-9800000000-c1dc75af0432077c03842016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopropylmaleic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9470000000-5b930a576d9e4924347a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopropylmaleic 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 - Isopropylmaleic acid 10V, Positive-QTOFsplash10-0006-1900000000-45d74194c5fbfea04a102015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 20V, Positive-QTOFsplash10-01ox-7900000000-7e85e22040474be6339c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 40V, Positive-QTOFsplash10-014j-9100000000-672bc73595a1f6b842012015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 10V, Negative-QTOFsplash10-0bt9-1900000000-48b9e2f85f15343470ae2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 20V, Negative-QTOFsplash10-090a-5900000000-5c4991c8530e2f8a6eda2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 40V, Negative-QTOFsplash10-00kb-9400000000-0d37fa6e2313dc5f09a32015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 10V, Positive-QTOFsplash10-01ow-6900000000-9e65c798b41317f5b6e92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 20V, Positive-QTOFsplash10-00kb-9200000000-6dfbad4c912b766f9b7e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 40V, Positive-QTOFsplash10-014i-9000000000-74dbf533069b6e671b6c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 10V, Negative-QTOFsplash10-03xr-9800000000-698f88590edad48bf4c22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 20V, Negative-QTOFsplash10-02t9-9400000000-d1228db2dbcd7906ae8a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopropylmaleic acid 40V, Negative-QTOFsplash10-014j-9000000000-a5bd12b0d9ab424964cc2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB028883
KNApSAcK IDNot Available
Chemspider ID4444164
KEGG Compound IDC02631
BioCyc IDCPD-9451
BiGG IDNot Available
Wikipedia LinkIsopropylmalic_acid
METLIN IDNot Available
PubChem Compound5280533
PDB IDNot Available
ChEBI ID17275
Food Biomarker OntologyNot Available
VMH ID2IPPM
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.