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Record Information
Version	2.0
Creation Date	2012-05-31 10:26:35 -0600
Update Date	2015-09-13 12:56:08 -0600
Secondary Accession Numbers	ECMDB00402
Identification
Name:	2-Isopropylmalic acid
Description	2-Isopropylmalic acid is involved in valine, leucine and isoleucine biosynthesis and pyruvate metabolism pathways. In pyruvate metabolism, 2-isopropylmalate synthase (EC:2.3.3.13) catalyzes the formation of 2-Isopropylmalic acid from acetyl-CoA. (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xace3482c> Close
Synonyms:	(2S)-2-Isopropylmalate (2S)-2-Isopropylmalic acid 2-D-Threo-hydroxy-3-carboxy-isocaproate 2-D-Threo-hydroxy-3-carboxy-isocaproic acid 2-Hydroxy-2-isopropylsuccinate 2-Hydroxy-2-isopropylsuccinic acid 2-Isopropyl-2-hydroxybutanedioate 2-Isopropyl-2-hydroxybutanedioic acid 2-Isopropyl-Malate 2-Isopropyl-Malic acid 2-Isopropylmalate 2-Isopropylmalic acid 3-Carboxy-2-hydroxy-4-methylpentanoate 3-Carboxy-2-hydroxy-4-methylpentanoic acid 3-Carboxy-3-hydroxyisocaproate 3-Carboxy-3-hydroxyisocaproic acid 3-Isopropylmalate 3-Isopropylmalic acid A-Isopropylmalate A-Isopropylmalic acid Alpha-Isopropylmalate Alpha-Isopropylmalic acid b-Isopropylmalate b-Isopropylmalic acid Beta-Isopropylmalate Beta-Isopropylmalic acid α-Isopropylmalate α-Isopropylmalic acid β-Isopropylmalate β-Isopropylmalic acid
Chemical Formula:	C7H12O5
Weight:	Average: 176.1672 Monoisotopic: 176.068473494
InChI Key:	BITYXLXUCSKTJS-ZETCQYMHSA-N
InChI:	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
CAS number:	3237-44-3
IUPAC Name:	(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid
Traditional IUPAC Name:	2-isopropyl-malic acid
SMILES:	CC(C)[C@@](O)(CC(O)=O)C(O)=O
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.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acids and conjugates
Direct Parent	Hydroxy fatty acids
Alternative Parents	Short-chain hydroxy acids and derivatives Methyl-branched fatty acids Dicarboxylic acids and derivatives Alpha hydroxy acids and derivatives Tertiary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	2-isopropylmalic acid (CHEBI:35128 ) Dicarboxylic acids (LMFA01170083 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	144-146 °C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 181 g/L ALOGPS logP -0.29 ALOGPS logP 0.21 ChemAxon logS 0.01 ALOGPS pKa (Strongest Acidic) 3.63 ChemAxon pKa (Strongest Basic) -4.1 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 94.83 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 38.58 m³·mol⁻¹ ChemAxon Polarizability 16.37 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:	Isopropylmaleate + Water <> 2-Isopropylmalic acid alpha-Ketoisovaleric acid + Acetyl-CoA + Water + a-Ketoisovaleric acid <> 2-Isopropylmalic acid + Coenzyme A + Hydrogen ion 2-Isopropylmalic acid + Coenzyme A <> Acetyl-CoA + alpha-Ketoisovaleric acid + Water 2-Isopropylmalic acid <> Isopropylmaleate + Water Acetyl-CoA + a-Ketoisovaleric acid + Water > 2-Isopropylmalic acid + CoA Isopropylmaleate + Water > 2-Isopropylmalic acid 3-Isopropylmalate + Isopropylmaleate + Water <> 2-Isopropylmalic acid 3-Methyl-2-oxovaleric acid + Water + Acetyl-CoA + 3-Methyl-2-oxovaleric acid > Coenzyme A + Hydrogen ion + 2-Isopropylmalic acid 2-Isopropylmalic acid > Water + Isopropylmaleate alpha-Ketoisovaleric acid + Acetyl-CoA + Water + a-Ketoisovaleric acid <>2 2-Isopropylmalic acid + Coenzyme A + Hydrogen ion
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 Pyruvate metabolism ec00620 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 splash10-0006-9400000000-1c869c73651e7e4e5dda View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-00bl-9134000000-30fabfd0c26c38444fff View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) splash10-004i-0900000000-1bb48f5ddadbf88b8f6c View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) splash10-00kr-9400000000-5df8f3f29d2e8a962cac View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) splash10-05n0-9200000000-c62b1543d0e6a41388f1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-014r-6900000000-983e4a8edd0725d26979 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-016r-1900000000-5aa4d41c6ff31081d9d7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-00di-9200000000-d4b84f7b5f2a53ac5800 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-0006-9000000000-c680094e514a83eea978 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-052o-9000000000-365c84abb7ec259fb43e View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-e28ea8cd657f96ff8357 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0690-1900000000-3b83300261e0daab2ef1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0006-9700000000-2652db028b01706ac042 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00di-9300000000-808bda4307e96bcfcc83 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-003r-2900000000-9fa33cd594a81b5d67cd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-055r-9700000000-8ab90438d0e6c9b7d0be View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4r-9100000000-41e1c40b755f8bfaf000 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01x9-9800000000-53afadde706df1ef69ab View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0006-9000000000-4bfe3581b4b94540fea0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-1470f6a6a1859e452712 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-2900000000-9a718ee22b675ce18980 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00kr-8900000000-188b5287c7dbbce2559f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-000l-9000000000-2a93d25f081bcaa86a53 View in MoNA 1D NMR 1H 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 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D 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 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 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 Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Schloss 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)
Links
External Links:	Resource Link CHEBI ID 28635 HMDB ID HMDB00402 Pubchem Compound ID 5280523 Kegg ID C02504 ChemSpider ID 4444155 Wikipedia ID Isopropylmalic acid BioCyc ID Not Available

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