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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:31:52 UTC
Update Date2023-02-21 17:25:21 UTC
HMDB IDHMDB0036395
Secondary Accession Numbers
  • HMDB36395
Metabolite Identification
Common Name2-Methylpropyl 3-oxobutanoate
Description2-Methylpropyl 3-oxobutanoate belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. 2-Methylpropyl 3-oxobutanoate is a sweet, brandy, and fruity tasting compound. Based on a literature review very few articles have been published on 2-Methylpropyl 3-oxobutanoate.
Structure
Data?1677000321
Synonyms
ValueSource
2-Methylpropyl 3-oxobutanoic acidGenerator
Acetoacetic acid, isobutyl esterHMDB
ACIBHMDB
Butanoic acid, 3-oxo-, 2-methylpropyl esterHMDB
FEMA 2177HMDB
Isobutyl 3-oxobutanoateHMDB
Isobutyl acetoacetateHMDB
Chemical FormulaC8H14O3
Average Molecular Weight158.195
Monoisotopic Molecular Weight158.094294314
IUPAC Name2-methylpropyl 3-oxobutanoate
Traditional Name2-methylpropyl 3-oxobutanoate
CAS Registry Number7779-75-1
SMILES
CC(C)COC(=O)CC(C)=O
InChI Identifier
InChI=1S/C8H14O3/c1-6(2)5-11-8(10)4-7(3)9/h6H,4-5H2,1-3H3
InChI KeyZYXNLVMBIHVDRH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassBeta-keto acids and derivatives
Direct ParentBeta-keto acids and derivatives
Alternative Parents
Substituents
  • Fatty acid ester
  • Beta-keto acid
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point196.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility17420 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.230 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.22 g/LALOGPS
logP0.99ALOGPS
logP1.39ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.05 m³·mol⁻¹ChemAxon
Polarizability17.05 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]+137.15931661259
DarkChem[M-H]-133.11831661259
DeepCCS[M+H]+139.79830932474
DeepCCS[M-H]-136.76230932474
DeepCCS[M-2H]-173.74830932474
DeepCCS[M+Na]+148.76530932474
AllCCS[M+H]+136.432859911
AllCCS[M+H-H2O]+132.632859911
AllCCS[M+NH4]+140.032859911
AllCCS[M+Na]+141.032859911
AllCCS[M-H]-136.832859911
AllCCS[M+Na-2H]-138.932859911
AllCCS[M+HCOO]-141.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methylpropyl 3-oxobutanoateCC(C)COC(=O)CC(C)=O1567.2Standard polar33892256
2-Methylpropyl 3-oxobutanoateCC(C)COC(=O)CC(C)=O1041.2Standard non polar33892256
2-Methylpropyl 3-oxobutanoateCC(C)COC(=O)CC(C)=O1106.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methylpropyl 3-oxobutanoate,1TMS,isomer #1CC(=CC(=O)OCC(C)C)O[Si](C)(C)C1300.0Semi standard non polar33892256
2-Methylpropyl 3-oxobutanoate,1TMS,isomer #1CC(=CC(=O)OCC(C)C)O[Si](C)(C)C1277.7Standard non polar33892256
2-Methylpropyl 3-oxobutanoate,1TMS,isomer #2C=C(CC(=O)OCC(C)C)O[Si](C)(C)C1253.9Semi standard non polar33892256
2-Methylpropyl 3-oxobutanoate,1TMS,isomer #2C=C(CC(=O)OCC(C)C)O[Si](C)(C)C1264.6Standard non polar33892256
2-Methylpropyl 3-oxobutanoate,1TBDMS,isomer #1CC(=CC(=O)OCC(C)C)O[Si](C)(C)C(C)(C)C1505.5Semi standard non polar33892256
2-Methylpropyl 3-oxobutanoate,1TBDMS,isomer #1CC(=CC(=O)OCC(C)C)O[Si](C)(C)C(C)(C)C1482.0Standard non polar33892256
2-Methylpropyl 3-oxobutanoate,1TBDMS,isomer #2C=C(CC(=O)OCC(C)C)O[Si](C)(C)C(C)(C)C1450.7Semi standard non polar33892256
2-Methylpropyl 3-oxobutanoate,1TBDMS,isomer #2C=C(CC(=O)OCC(C)C)O[Si](C)(C)C(C)(C)C1466.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylpropyl 3-oxobutanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-1651f073cbf032c123e02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylpropyl 3-oxobutanoate 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-Methylpropyl 3-oxobutanoate 10V, Positive-QTOFsplash10-0a4i-8900000000-8d22b72300ba624296282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 20V, Positive-QTOFsplash10-0a4i-9100000000-b13aadf248760f14a6e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 40V, Positive-QTOFsplash10-0a4i-9000000000-7d24f841eadc505025132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 10V, Negative-QTOFsplash10-0a59-8900000000-9554d900bd23e9773f182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 20V, Negative-QTOFsplash10-0a59-9400000000-650e600e3fa08377b3582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 40V, Negative-QTOFsplash10-0a59-9000000000-1074f050fca1907fe5722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 10V, Negative-QTOFsplash10-00di-9000000000-81b42c092cc1bf1cb6b42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 20V, Negative-QTOFsplash10-0019-9700000000-ac055b724e00ec103cdb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 40V, Negative-QTOFsplash10-0ab9-9000000000-bb05d98696f3549681e62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 10V, Positive-QTOFsplash10-0a4l-9000000000-6bbd0e2dce65753bcf732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 20V, Positive-QTOFsplash10-052f-9000000000-04e5c133e269bb7295952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylpropyl 3-oxobutanoate 40V, Positive-QTOFsplash10-052f-9000000000-d3bf30a1e3e6f9aadf5c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB015274
KNApSAcK IDNot Available
Chemspider ID21105926
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound522677
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1013091
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .