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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:02 UTC
Update Date2021-09-14 15:45:29 UTC
HMDB IDHMDB0012149
Secondary Accession Numbers
  • HMDB12149
Metabolite Identification
Common Name2-Isopropyl-3-oxosuccinate
Description2-Isopropyl-3-oxosuccinate belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain that contains less than 6 carbon atoms. 2-Isopropyl-3-oxosuccinate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Isopropyl-3-oxosuccinate exists in all living species, ranging from bacteria to humans. 2-Isopropyl-3-oxosuccinate has been detected, but not quantified in, several different foods, such as garden onion (var.), German camomiles, limes, cloud ear fungus, and citrus. This could make 2-isopropyl-3-oxosuccinate a potential biomarker for the consumption of these foods. 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 into 4-methyl-2-oxopentanoate via a spontaneous reaction (BioCyc).
Structure
Data?1583942437
Synonyms
ValueSource
(2S)-2-(1-Methylethyl)-3-oxobutanedioic acidChEBI
(2S)-2-Isopropyl-3-oxosuccinateChEBI
3-Carboxy-4-methyl-2-oxopentanoateChEBI
2-oxo-4-Methyl-3-carboxypentanoateKegg
(2S)-2-(1-Methylethyl)-3-oxobutanedioateGenerator
(2S)-2-Isopropyl-3-oxosuccinic acidGenerator
3-Carboxy-4-methyl-2-oxopentanoic acidGenerator
2-oxo-4-Methyl-3-carboxypentanoic acidGenerator
2-Isopropyl-3-oxosuccinic acidGenerator
(2S)-3-oxo-2-(Propan-2-yl)butanedioateHMDB
(2S)-3-oxo-2-(Propan-2-yl)butanedioic acidHMDB
2-(1-Methylethyl)-3-oxobutanedioic acidHMDB
2-Oxo-3-isopropylsuccinic acidHMDB
Chemical FormulaC7H10O5
Average Molecular Weight174.1513
Monoisotopic Molecular Weight174.05282343
IUPAC Name(3S)-2-oxo-3-(propan-2-yl)butanedioic acid
Traditional Name(2S)-2-isopropyl-3-oxobutanedioic acid
CAS Registry Number1245945-28-1
SMILES
CC(C)[C@H](C(O)=O)C(=O)C(O)=O
InChI Identifier
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
InChI KeyHIIZAGQWABAMRR-BYPYZUCNSA-N
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
Process
RoleNot Available
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 Solubility7.02 g/LALOGPS
logP0.43ALOGPS
logP1.23ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)-10ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.06 m³·mol⁻¹ChemAxon
Polarizability15.83 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]+140.16731661259
DarkChem[M-H]-137.93731661259
DeepCCS[M+H]+135.25330932474
DeepCCS[M-H]-132.2330932474
DeepCCS[M-2H]-168.68830932474
DeepCCS[M+Na]+144.22730932474
AllCCS[M+H]+138.132859911
AllCCS[M+H-H2O]+134.232859911
AllCCS[M+NH4]+141.632859911
AllCCS[M+Na]+142.632859911
AllCCS[M-H]-133.232859911
AllCCS[M+Na-2H]-134.832859911
AllCCS[M+HCOO]-136.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Isopropyl-3-oxosuccinateCC(C)[C@H](C(O)=O)C(=O)C(O)=O2136.4Standard polar33892256
2-Isopropyl-3-oxosuccinateCC(C)[C@H](C(O)=O)C(=O)C(O)=O1311.4Standard non polar33892256
2-Isopropyl-3-oxosuccinateCC(C)[C@H](C(O)=O)C(=O)C(O)=O1414.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Isopropyl-3-oxosuccinate,1TMS,isomer #1CC(C)[C@H](C(=O)O[Si](C)(C)C)C(=O)C(=O)O1408.2Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,1TMS,isomer #2CC(C)[C@H](C(=O)O)C(=O)C(=O)O[Si](C)(C)C1390.3Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,1TMS,isomer #3CC(C)C(C(=O)O)=C(O[Si](C)(C)C)C(=O)O1496.4Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,2TMS,isomer #1CC(C)[C@H](C(=O)O[Si](C)(C)C)C(=O)C(=O)O[Si](C)(C)C1514.1Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,2TMS,isomer #2CC(C)C(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)O1566.7Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,2TMS,isomer #3CC(C)C(C(=O)O)=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1548.0Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,3TMS,isomer #1CC(C)C(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1596.1Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,3TMS,isomer #1CC(C)C(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1610.7Standard non polar33892256
2-Isopropyl-3-oxosuccinate,3TMS,isomer #1CC(C)C(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1565.9Standard polar33892256
2-Isopropyl-3-oxosuccinate,1TBDMS,isomer #1CC(C)[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O1654.2Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,1TBDMS,isomer #2CC(C)[C@H](C(=O)O)C(=O)C(=O)O[Si](C)(C)C(C)(C)C1626.4Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,1TBDMS,isomer #3CC(C)C(C(=O)O)=C(O[Si](C)(C)C(C)(C)C)C(=O)O1749.1Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,2TBDMS,isomer #1CC(C)[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C(=O)O[Si](C)(C)C(C)(C)C1938.9Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,2TBDMS,isomer #2CC(C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)O1973.6Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,2TBDMS,isomer #3CC(C)C(C(=O)O)=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2013.1Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,3TBDMS,isomer #1CC(C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2205.7Semi standard non polar33892256
2-Isopropyl-3-oxosuccinate,3TBDMS,isomer #1CC(C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2200.6Standard non polar33892256
2-Isopropyl-3-oxosuccinate,3TBDMS,isomer #1CC(C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2060.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropyl-3-oxosuccinate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-a431ad34a78f0adc25af2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropyl-3-oxosuccinate GC-MS (2 TMS) - 70eV, Positivesplash10-0g74-9331000000-f234980692c6ed06a94e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropyl-3-oxosuccinate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Isopropyl-3-oxosuccinate 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 - 2-Isopropyl-3-oxosuccinate 10V, Positive-QTOFsplash10-056r-1900000000-acd1ea66574d55eb331d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 20V, Positive-QTOFsplash10-06v0-5900000000-7e737232c4fb38bff3bf2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 40V, Positive-QTOFsplash10-001i-9600000000-844c8da366f084302d2b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 10V, Negative-QTOFsplash10-00b9-1900000000-bdd65fc36b7ec2c689152015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 20V, Negative-QTOFsplash10-057i-7900000000-31ff420a87e647dd11542015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 40V, Negative-QTOFsplash10-00e9-9100000000-ffbf76307b5afc43379b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 10V, Negative-QTOFsplash10-01t9-2900000000-dea633070d58aa2d42982021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 20V, Negative-QTOFsplash10-00ar-9800000000-562cf1d81cbf0e6dfda12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 40V, Negative-QTOFsplash10-001i-9000000000-27319b151cd6c10b30ce2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 10V, Positive-QTOFsplash10-06ui-4900000000-5bcfc8907d6248e329002021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 20V, Positive-QTOFsplash10-001i-9000000000-f03654c5ee61af92206e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Isopropyl-3-oxosuccinate 40V, Positive-QTOFsplash10-0a4i-9000000000-47f8865805b71fe90ddd2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB028806
KNApSAcK IDNot Available
Chemspider ID4575347
KEGG Compound IDC04236
BioCyc IDCPD-7100
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5462259
PDB IDNot Available
ChEBI ID1467
Food Biomarker OntologyNot Available
VMH ID3C4MOP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available