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Record Information
Version	2.0
Creation Date	2012-05-31 14:20:46 -0600
Update Date	2015-06-03 17:19:02 -0600
Secondary Accession Numbers	ECMDB12149
Identification
Name:	2-Isopropyl-3-oxosuccinate
Description	2-Isopropyl-3-oxosuccinate is an intermediate in leucine biosynthesis and can be generated from (2R,3S)-3-Isopropylmalate. It is the third step in leucine biosynthesis after the fork from valine synthesis. It is an oxidative decarboxylation. 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). In this pathway 2-Isopropyl-3-oxosuccinate is converted to 4-Methyl-2-oxopentanoate via spontaneous reaction.(BioCyc)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa2438ee0> Close
Synonyms:	(2S)-2-(1-methylethyl)-3-oxobutanedioate (2S)-2-(1-methylethyl)-3-oxobutanedioic acid (2S)-2-Isopropyl-3-oxosuccinate (2S)-2-isopropyl-3-oxosuccinic acid (2S)-3-oxo-2-(propan-2-yl)butanedioate (2S)-3-oxo-2-(propan-2-yl)butanedioic acid 2-isopropyl-3-oxosuccinate 2-Isopropyl-3-oxosuccinic acid 2-Oxo-4-methyl-3-carboxypentanoate 2-Oxo-4-methyl-3-carboxypentanoic acid 3-Carboxy-4-methyl-2-oxopentanoate 3-Carboxy-4-methyl-2-oxopentanoic acid
Chemical Formula:	C7H10O5
Weight:	Average: 174.1513 Monoisotopic: 174.05282343
InChI Key:	HIIZAGQWABAMRR-BYPYZUCNSA-N
InChI:	InChI=1S/C7H10O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-4H,1-2H3,(H,9,10)(H,11,12)/t4-/m0/s1
CAS number:	Not Available
IUPAC Name:	(3S)-2-oxo-3-(propan-2-yl)butanedioic acid
Traditional IUPAC Name:	(2S)-2-isopropyl-3-oxobutanedioic acid
SMILES:	CC(C)[C@H](C(O)=O)C(=O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Short-chain keto acids and derivatives
Direct Parent	Short-chain keto acids and derivatives
Alternative Parents	Methyl-branched fatty acids Beta-keto acids and derivatives Dicarboxylic acids and derivatives Beta-hydroxy ketones Alpha-keto acids and derivatives 1,3-dicarbonyl compounds Alpha-hydroxy ketones Carboxylic acids Organic oxides Hydrocarbon derivatives
Substituents	Beta-keto acid Branched fatty acid Short-chain keto acid Methyl-branched fatty acid Alpha-keto acid Beta-hydroxy ketone Dicarboxylic acid or derivatives 1,3-dicarbonyl compound Fatty acyl Alpha-hydroxy ketone Ketone Carboxylic acid Carboxylic acid derivative Carbonyl group Organic oxide Organooxygen compound Hydrocarbon derivative Organic oxygen compound Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	oxo dicarboxylic acid (CHEBI:1467 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 7.02 g/L ALOGPS logP 0.43 ALOGPS logP 1.23 ChemAxon logS -1.4 ALOGPS pKa (Strongest Acidic) 2.93 ChemAxon pKa (Strongest Basic) -10 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 91.67 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 38.06 m³·mol⁻¹ ChemAxon Polarizability 15.83 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 + NAD > 2-Isopropyl-3-oxosuccinate + Hydrogen ion + NADH 2-Isopropyl-3-oxosuccinate + Hydrogen ion > Ketoleucine + Carbon dioxide 3-Isopropylmalate + NAD <> 2-Isopropyl-3-oxosuccinate + NADH + Hydrogen ion 3-Isopropylmalate + NAD + 2-Isopropyl-3-oxosuccinate <> Ketoleucine + Carbon dioxide + NADH + Hydrogen ion 3 3-Isopropylmalate + NAD >2 2-Isopropyl-3-oxosuccinate + Hydrogen ion + NADH 3 3-Isopropylmalate + NAD >2 2-Isopropyl-3-oxosuccinate + Hydrogen ion + NADH
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 Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0006-9600000000-a431ad34a78f0adc25af View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-0g74-9331000000-f234980692c6ed06a94e 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 (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-056r-1900000000-acd1ea66574d55eb331d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-06v0-5900000000-7e737232c4fb38bff3bf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-001i-9600000000-844c8da366f084302d2b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00b9-1900000000-bdd65fc36b7ec2c68915 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-057i-7900000000-31ff420a87e647dd1154 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00e9-9100000000-ffbf76307b5afc43379b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-01t9-2900000000-dea633070d58aa2d4298 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00ar-9800000000-562cf1d81cbf0e6dfda1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-001i-9000000000-27319b151cd6c10b30ce View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-06ui-4900000000-5bcfc8907d6248e32900 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-001i-9000000000-f03654c5ee61af92206e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9000000000-47f8865805b71fe90ddd 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 1467 HMDB ID HMDB12149 Pubchem Compound ID 5462259 Kegg ID C04236 ChemSpider ID 4575347 Wikipedia ID Not Available BioCyc ID CPD-7100 EcoCyc ID CPD-7100

Enzymes