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Record Information
Version	2.0
Creation Date	2012-05-31 14:21:15 -0600
Update Date	2015-06-03 17:19:03 -0600
Secondary Accession Numbers	ECMDB12241
Identification
Name:	Isopropylmaleate
Description	Isopropylmaleate is an intermediate in branched chain amino acid metabolism (specifically L-leucine biosynthesis). It is a substrate for 3-isopropylmalate dehydratase. This enzyme catalyzes the isomerization between 2-isopropylmalate and 3-isopropylmalate, via the formation of 2-isopropylmaleate.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae8a1d7c> Close
Synonyms:	β-isopropylmaleate β-isopropylmaleic acid 2-Isopropylmaleate 2-Isopropylmaleic acid B-isopropylmaleate b-Isopropylmaleic acid Beta-Isopropylmaleate Beta-Isopropylmaleic acid Isopropylmaleic acid β-Isopropylmaleate β-Isopropylmaleic acid
Chemical Formula:	C7H10O4
Weight:	Average: 158.1519 Monoisotopic: 158.057908808
InChI Key:	NJMGRJLQRLFQQX-HYXAFXHYSA-N
InChI:	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-
CAS number:	Not Available
IUPAC Name:	(2Z)-2-(propan-2-yl)but-2-enedioic acid
Traditional IUPAC Name:	2-isopropylmaleic acid
SMILES:	CC(C)C(=C\C(O)=O)\C(O)=O
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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acids and conjugates
Direct Parent	Methyl-branched fatty acids
Alternative Parents	Unsaturated fatty acids Dicarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	dicarboxylic acid (CHEBI:17275 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.64 g/L ALOGPS logP 1.05 ALOGPS logP 1.09 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 2.79 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 74.6 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 38.11 m³·mol⁻¹ ChemAxon Polarizability 15.11 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	3-Isopropylmalate <> Isopropylmaleate + Water Isopropylmaleate + Water <> 2-Isopropylmalic acid 2-Isopropylmalic acid <> Isopropylmaleate + Water 3-Carboxy-3-hydroxy-isocaproate <> Isopropylmaleate + Water 3-Isopropylmalate < Isopropylmaleate + Water 3-Isopropylmalate > Isopropylmaleate + Water Isopropylmaleate + Water > 2-Isopropylmalic acid 3-Isopropylmalate + Isopropylmaleate + Water <> 2-Isopropylmalic acid 2-Isopropylmalic acid > Water + Isopropylmaleate Isopropylmaleate + Water > 3-Isopropylmalate 3 3-Isopropylmalate <> Isopropylmaleate + Water 3 3-Isopropylmalate <> Isopropylmaleate + Water
SMPDB Pathways:	Leucine Biosynthesis PW000811 Secondary Metabolite: Leucine biosynthesis PW000980 Secondary Metabolites: Valine and I-leucine biosynthesis from pyruvate PW000978
KEGG Pathways:	Metabolic pathways eco01100 Valine, leucine and isoleucine biosynthesis ec00290
EcoCyc Pathways:	isoleucine biosynthesis I (from threonine) LEUSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-01ox-9800000000-c1dc75af0432077c0384 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-00dr-9470000000-5b930a576d9e4924347a View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0006-1900000000-45d74194c5fbfea04a10 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01ox-7900000000-7e85e22040474be6339c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014j-9100000000-672bc73595a1f6b84201 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0bt9-1900000000-48b9e2f85f15343470ae View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-090a-5900000000-5c4991c8530e2f8a6eda View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00kb-9400000000-0d37fa6e2313dc5f09a3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01ow-6900000000-9e65c798b41317f5b6e9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00kb-9200000000-6dfbad4c912b766f9b7e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014i-9000000000-74dbf533069b6e671b6c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03xr-9800000000-698f88590edad48bf4c2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-02t9-9400000000-d1228db2dbcd7906ae8a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-014j-9000000000-a5bd12b0d9ab424964cc View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 17275 HMDB ID HMDB12241 Pubchem Compound ID 230410 Kegg ID C02631 ChemSpider ID 4444164 Wikipedia ID Isopropylmalic_acid BioCyc ID CPD-9451 EcoCyc ID CPD-9451

Enzymes