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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2014-10-08 15:56:30 UTC
Update Date2018-05-20 00:03:38 UTC
HMDB IDHMDB0061881
Secondary Accession Numbers
  • HMDB61881
Metabolite Identification
Common Name4-Acetylbutyrate
Description5-Keto-N-caproic acid, also known as 4-acetylbutyric acid or 5-oxohexanoate, 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. 5-Keto-N-caproic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 5-Keto-N-caproic acid has been detected in multiple biofluids, such as saliva and urine. Within the cell, 5-keto-N-caproic acid is primarily located in the cytoplasm and adiposome. 5-Keto-N-caproic acid can be biosynthesized from hexanoic acid.
Structure
Thumb
Synonyms
ValueSource
4-Acetyl-butanoic acidChEBI
4-Acetyl-butyric acidChEBI
4-Acetylbutyric acidChEBI
5-Ketocaproic acidChEBI
5-Ketohexanoic acidChEBI
5-Oxocaproic acidChEBI
5-OxohexanoateChEBI
delta-Ketocaproic acidChEBI
delta-Oxocaproic acidChEBI
gamma-Acetylbutyric acidChEBI
4-Acetyl-butanoateGenerator
5-keto-N-CaproateGenerator
4-Acetyl-butyrateGenerator
4-AcetylbutyrateGenerator
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
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
DescriptionThis compound 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility50.9 g/LALOGPS
logP0.05ALOGPS
logP0.38ChemAxon
logS-0.41ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-d74c72d28c30ba47007aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0076-9300000000-2f4f5d82002d35670cb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-4900000000-06d2e7c20000d95cb762View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xs-9400000000-d502e3776bf8ee1dacf8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9000000000-c8dc2c5b57bc872311e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-c8bc1ee45afd87b963f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vr-6900000000-443256d51dd82e63bc96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-263637adefeac595de6aView in MoNA
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
FoodDB 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
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]