Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-05-31 14:06:45 -0600
Update Date	2015-06-03 15:54:48 -0600
Secondary Accession Numbers	ECMDB04158
Identification
Name:	3-Isopropylmalate
Description	3-Isopropylmalate is an intermediate in valine, leucine and isoleucine biosynthesis. It is a substrate for 3-isopropylmalate dehydrogenase (TT_C0867)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xac3eb014> Close
Synonyms:	β-isopropylmalate β-isopropylmalic acid (2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioate (2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid (2R,3S)-2-hydroxy-3-isopropylsuccinate (2R,3S)-2-hydroxy-3-isopropylsuccinic acid (2R,3S)-3-carboxy-2-hydroxy-4-methylpentanoate (2R,3S)-3-carboxy-2-hydroxy-4-methylpentanoic acid (2R,3S)-3-Isopropylmalate (2R,3S)-3-isopropylmalic acid 2-D-Threo-Hydroxy-3-carboxy-isocaproate 2-D-Threo-Hydroxy-3-carboxy-isocaproic acid 2-D-Threo-hydroxy-3-carboxyisocaproate 2-D-Threo-hydroxy-3-carboxyisocaproic acid 3-3-Isopropylmalate 3-3-Isopropylmalic acid 3-Carboxy-2-hydroxy-4-methylpentanoate 3-Carboxy-2-hydroxy-4-methylpentanoic acid 3-isopropylmalate 3-Isopropylmalic acid 3IPMA b-Isopropylmalate b-Isopropylmalic acid Beta-Isopropylmalate Beta-Isopropylmalic acid IPM β-Isopropylmalate β-Isopropylmalic acid
Chemical Formula:	C7H12O5
Weight:	Average: 176.1672 Monoisotopic: 176.068473494
InChI Key:	RNQHMTFBUSSBJQ-CRCLSJGQSA-N
InChI:	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
CAS number:	921-28-8
IUPAC Name:	(2R,3S)-2-hydroxy-3-(propan-2-yl)butanedioic acid
Traditional IUPAC Name:	(2R,3S)-3-isopropylmalic acid
SMILES:	CC(C)[C@@H]([C@@H](O)C(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 Beta hydroxy acids and derivatives Dicarboxylic acids and derivatives Alpha hydroxy acids and derivatives Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	3-isopropylmalic acid (CHEBI:43468 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 83.3 g/L ALOGPS logP 0.28 ALOGPS logP 0.16 ChemAxon logS -0.33 ALOGPS pKa (Strongest Acidic) 3.68 ChemAxon pKa (Strongest Basic) -4 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 38.6 m³·mol⁻¹ ChemAxon Polarizability 16.47 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 3-Isopropylmalate + NAD > 2-Isopropyl-3-oxosuccinate + Hydrogen ion + NADH 3-Isopropylmalate + NAD <> 2-Isopropyl-3-oxosuccinate + NADH + Hydrogen ion 3-Isopropylmalate < Isopropylmaleate + Water 3-Isopropylmalate + NAD > Ketoleucine + Carbon dioxide + NADH 3-Isopropylmalate > Isopropylmaleate + Water 3-Isopropylmalate + Isopropylmaleate + Water <> 2-Isopropylmalic acid 3-Isopropylmalate + NAD + 2-Isopropyl-3-oxosuccinate <> Ketoleucine + Carbon dioxide + NADH + Hydrogen ion Isopropylmaleate + Water > 3-Isopropylmalate 3 3-Isopropylmalate + NAD >2 2-Isopropyl-3-oxosuccinate + Hydrogen ion + NADH 3 3-Isopropylmalate <> Isopropylmaleate + Water 3 3-Isopropylmalate + NAD >2 2-Isopropyl-3-oxosuccinate + Hydrogen ion + NADH 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:	C5-Branched dibasic acid metabolism ec00660 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 GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0002-0920000000-4ec856cc4eb69ab95ccc View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0002-0920000000-4ec856cc4eb69ab95ccc View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0006-9400000000-a5c729805d94db1fb7b3 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-00bl-9135000000-1982df651c1931669dae 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 splash10-0a7i-1900000000-224a91a676e183e74333 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-06sl-7900000000-b06817c1e6edcae6d425 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-052o-9300000000-479bb2145817abc0bf1a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0059-1900000000-acde792ba60cae65a216 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0far-9700000000-cf8f9dd2b32cfd503f42 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a59-9100000000-138111afc561c6d0a2ec View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03ei-3900000000-99922dc6120c0bc9d5ac View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-9300000000-6c8d0a906ce3776c4769 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-052f-9000000000-229b51add43b0209aa10 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-1900000000-bcc925b37cd5d5f31b5a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01q0-7900000000-222a48c445cf7526d6e6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0019-9100000000-6003ddbcaf34c522b89a View in MoNA 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
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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 35114 HMDB ID HMDB12156 Pubchem Compound ID 5462261 Kegg ID C04411 ChemSpider ID 4575349 Wikipedia ID Isopropylmalic acid BioCyc ID 2-D-THREO-HYDROXY-3-CARBOXY-ISOCAPROATE EcoCyc ID 2-D-THREO-HYDROXY-3-CARBOXY-ISOCAPROATE Ligand Expo IPM

Enzymes