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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2014-10-08 15:56:30 UTC
Update Date2019-07-23 07:17:22 UTC
HMDB IDHMDB0061881
Secondary Accession Numbers
  • HMDB61881
Metabolite Identification
Common Name4-Acetylbutyrate
Description4-Acetylbutyrate, also known as 5-oxohexanoate or 5-ketocaproic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 4-Acetylbutyrate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866242
Synonyms
ValueSource
4-Acetyl-butanoic acidChEBI
4-Acetyl-butyric acidChEBI
4-Acetylbutyric acidChEBI
5-Keto-N-caproic acidChEBI
5-Ketocaproic acidChEBI
5-Ketohexanoic acidChEBI
5-Oxocaproic acidChEBI
5-OxohexanoateChEBI
delta-Ketocaproic acidChEBI
delta-Oxocaproic acidChEBI
gamma-Acetylbutyric acidChEBI
4-Acetyl-butanoateGenerator
4-Acetyl-butyrateGenerator
5-Keto-N-caproateGenerator
5-KetocaproateGenerator
5-KetohexanoateGenerator
5-OxocaproateGenerator
5-Oxohexanoic acidGenerator
delta-KetocaproateGenerator
Δ-ketocaproateGenerator
Δ-ketocaproic acidGenerator
delta-OxocaproateGenerator
Δ-oxocaproateGenerator
Δ-oxocaproic acidGenerator
g-AcetylbutyrateGenerator
g-Acetylbutyric acidGenerator
gamma-AcetylbutyrateGenerator
Γ-acetylbutyrateGenerator
Γ-acetylbutyric acidGenerator
4-AcetylbutyrateGenerator
Chemical FormulaC6H10O3
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
IUPAC Name5-oxohexanoic acid
Traditional Name5-oxohexanoic acid
CAS Registry Number3128-06-1
SMILES
CC(=O)CCCC(O)=O
InChI Identifier
InChI=1S/C6H10O3/c1-5(7)3-2-4-6(8)9/h2-4H2,1H3,(H,8,9)
InChI KeyMGTZCLMLSSAXLD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
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 Solubility50.9 g/LALOGPS
logP10(0.05) g/LALOGPS
logP10(0.38) g/LChemAxon
logS10(-0.41) g/LALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.69 m³·mol⁻¹ChemAxon
Polarizability13.22 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]+129.24931661259
DarkChem[M-H]-123.93931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-AcetylbutyrateCC(=O)CCCC(O)=O2376.7Standard polar33892256
4-AcetylbutyrateCC(=O)CCCC(O)=O1059.8Standard non polar33892256
4-AcetylbutyrateCC(=O)CCCC(O)=O1164.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Acetylbutyrate,1TMS,isomer #1CC(=O)CCCC(=O)O[Si](C)(C)C1246.2Semi standard non polar33892256
4-Acetylbutyrate,1TMS,isomer #2CC(=CCCC(=O)O)O[Si](C)(C)C1355.8Semi standard non polar33892256
4-Acetylbutyrate,1TMS,isomer #3C=C(CCCC(=O)O)O[Si](C)(C)C1329.4Semi standard non polar33892256
4-Acetylbutyrate,2TMS,isomer #1CC(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C1438.0Semi standard non polar33892256
4-Acetylbutyrate,2TMS,isomer #1CC(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C1371.7Standard non polar33892256
4-Acetylbutyrate,2TMS,isomer #1CC(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C1441.0Standard polar33892256
4-Acetylbutyrate,2TMS,isomer #2C=C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C1385.2Semi standard non polar33892256
4-Acetylbutyrate,2TMS,isomer #2C=C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C1397.0Standard non polar33892256
4-Acetylbutyrate,2TMS,isomer #2C=C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C1462.0Standard polar33892256
4-Acetylbutyrate,1TBDMS,isomer #1CC(=O)CCCC(=O)O[Si](C)(C)C(C)(C)C1468.4Semi standard non polar33892256
4-Acetylbutyrate,1TBDMS,isomer #2CC(=CCCC(=O)O)O[Si](C)(C)C(C)(C)C1596.1Semi standard non polar33892256
4-Acetylbutyrate,1TBDMS,isomer #3C=C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C1557.7Semi standard non polar33892256
4-Acetylbutyrate,2TBDMS,isomer #1CC(=CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1862.9Semi standard non polar33892256
4-Acetylbutyrate,2TBDMS,isomer #1CC(=CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1827.5Standard non polar33892256
4-Acetylbutyrate,2TBDMS,isomer #1CC(=CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1747.1Standard polar33892256
4-Acetylbutyrate,2TBDMS,isomer #2C=C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1839.0Semi standard non polar33892256
4-Acetylbutyrate,2TBDMS,isomer #2C=C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1814.0Standard non polar33892256
4-Acetylbutyrate,2TBDMS,isomer #2C=C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1765.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylbutyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-d74c72d28c30ba47007a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylbutyrate GC-MS (1 TMS) - 70eV, Positivesplash10-0076-9300000000-2f4f5d82002d35670cb12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetylbutyrate 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 - 4-Acetylbutyrate 10V, Positive-QTOFsplash10-03dj-4900000000-06d2e7c20000d95cb7622017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 20V, Positive-QTOFsplash10-03xs-9400000000-d502e3776bf8ee1dacf82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 40V, Positive-QTOFsplash10-0uxr-9000000000-c8dc2c5b57bc872311e42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 10V, Negative-QTOFsplash10-004i-1900000000-c8bc1ee45afd87b963f22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 20V, Negative-QTOFsplash10-06vr-6900000000-443256d51dd82e63bc962017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 40V, Negative-QTOFsplash10-0a4l-9000000000-263637adefeac595de6a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 10V, Negative-QTOFsplash10-01ri-6900000000-f5fb9cf43d60e2bdb1f82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 20V, Negative-QTOFsplash10-0a4i-9000000000-6822ee7f89ce916c4f6b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 40V, Negative-QTOFsplash10-0a4l-9000000000-b5186cf0c530754526e02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 10V, Positive-QTOFsplash10-03dv-9300000000-04fbb62fc5704c241ad22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 20V, Positive-QTOFsplash10-0006-9000000000-7e2799bc14a0fef960c72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetylbutyrate 40V, Positive-QTOFsplash10-0006-9000000000-be67ec0679994457ee2c2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.349 +/- 0.124 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.357 +/- 0.167 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.366 +/- 0.242 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.417 +/- 0.137 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.446 +/- 0.157 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.523 +/- 0.224 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02129
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18407
PDB IDNot Available
ChEBI ID15888
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  6. Robin E. Osterhout, Anthony P. Burgard, Mark J. Burk, Priti Pharkya, 'ORGANISMS FOR THE PRODUCTION OF CYCLOHEXANONE.' U.S. Patent US20110014668, issued January 20, 2011. [Link]