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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2014-10-08 15:56:30 UTC

Update Date

2023-02-21 17:30:32 UTC

HMDB ID

HMDB0061881

Secondary Accession Numbers

HMDB61881

Metabolite Identification

Common Name

4-Acetylbutyrate

Description

4-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Acetyl-butanoic acid	ChEBI
4-Acetyl-butyric acid	ChEBI
4-Acetylbutyric acid	ChEBI
5-Keto-N-caproic acid	ChEBI
5-Ketocaproic acid	ChEBI
5-Ketohexanoic acid	ChEBI
5-Oxocaproic acid	ChEBI
5-Oxohexanoate	ChEBI
delta-Ketocaproic acid	ChEBI
delta-Oxocaproic acid	ChEBI
gamma-Acetylbutyric acid	ChEBI
4-Acetyl-butanoate	Generator
4-Acetyl-butyrate	Generator
5-Keto-N-caproate	Generator
5-Ketocaproate	Generator
5-Ketohexanoate	Generator
5-Oxocaproate	Generator
5-Oxohexanoic acid	Generator
delta-Ketocaproate	Generator
Δ-ketocaproate	Generator
Δ-ketocaproic acid	Generator
delta-Oxocaproate	Generator
Δ-oxocaproate	Generator
Δ-oxocaproic acid	Generator
g-Acetylbutyrate	Generator
g-Acetylbutyric acid	Generator
gamma-Acetylbutyrate	Generator
Γ-acetylbutyrate	Generator
Γ-acetylbutyric acid	Generator
4-Acetylbutyrate	Generator

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

IUPAC Name

5-oxohexanoic acid

Traditional Name

5-oxohexanoic acid

CAS Registry Number

3128-06-1

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 Key

MGTZCLMLSSAXLD-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

5-oxo monocarboxylic acid (CHEBI:15888 )
medium-chain fatty acid (CHEBI:15888 )
straight-chain fatty acid (CHEBI:15888 )
oxo fatty acid (CHEBI:15888 )
Oxo fatty acids (C02129 )
Oxo fatty acids (LMFA01060010 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0061881)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	50.9 g/L	ALOGPS
logP	0.05	ALOGPS
logP	0.38	ChemAxon
logS	-0.41	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.69 m³·mol⁻¹	ChemAxon
Polarizability	13.22 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.249	31661259
DarkChem	[M-H]-	123.939	31661259
DeepCCS	[M+H]+	128.31	30932474
DeepCCS	[M-H]-	125.472	30932474
DeepCCS	[M-2H]-	161.829	30932474
DeepCCS	[M+Na]+	136.874	30932474
AllCCS	[M+H]+	130.2	32859911
AllCCS	[M+H-H2O]+	126.0	32859911
AllCCS	[M+NH4]+	134.1	32859911
AllCCS	[M+Na]+	135.2	32859911
AllCCS	[M-H]-	128.5	32859911
AllCCS	[M+Na-2H]-	131.2	32859911
AllCCS	[M+HCOO]-	134.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Acetylbutyrate	CC(=O)CCCC(O)=O	2376.7	Standard polar	33892256
4-Acetylbutyrate	CC(=O)CCCC(O)=O	1059.8	Standard non polar	33892256
4-Acetylbutyrate	CC(=O)CCCC(O)=O	1164.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Acetylbutyrate,1TMS,isomer #1	CC(=O)CCCC(=O)O[Si](C)(C)C	1246.2	Semi standard non polar	33892256
4-Acetylbutyrate,1TMS,isomer #2	CC(=CCCC(=O)O)O[Si](C)(C)C	1355.8	Semi standard non polar	33892256
4-Acetylbutyrate,1TMS,isomer #3	C=C(CCCC(=O)O)O[Si](C)(C)C	1329.4	Semi standard non polar	33892256
4-Acetylbutyrate,2TMS,isomer #1	CC(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1438.0	Semi standard non polar	33892256
4-Acetylbutyrate,2TMS,isomer #1	CC(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1371.7	Standard non polar	33892256
4-Acetylbutyrate,2TMS,isomer #1	CC(=CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1441.0	Standard polar	33892256
4-Acetylbutyrate,2TMS,isomer #2	C=C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1385.2	Semi standard non polar	33892256
4-Acetylbutyrate,2TMS,isomer #2	C=C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1397.0	Standard non polar	33892256
4-Acetylbutyrate,2TMS,isomer #2	C=C(CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1462.0	Standard polar	33892256
4-Acetylbutyrate,1TBDMS,isomer #1	CC(=O)CCCC(=O)O[Si](C)(C)C(C)(C)C	1468.4	Semi standard non polar	33892256
4-Acetylbutyrate,1TBDMS,isomer #2	CC(=CCCC(=O)O)O[Si](C)(C)C(C)(C)C	1596.1	Semi standard non polar	33892256
4-Acetylbutyrate,1TBDMS,isomer #3	C=C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C	1557.7	Semi standard non polar	33892256
4-Acetylbutyrate,2TBDMS,isomer #1	CC(=CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1862.9	Semi standard non polar	33892256
4-Acetylbutyrate,2TBDMS,isomer #1	CC(=CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1827.5	Standard non polar	33892256
4-Acetylbutyrate,2TBDMS,isomer #1	CC(=CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1747.1	Standard polar	33892256
4-Acetylbutyrate,2TBDMS,isomer #2	C=C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1839.0	Semi standard non polar	33892256
4-Acetylbutyrate,2TBDMS,isomer #2	C=C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1814.0	Standard non polar	33892256
4-Acetylbutyrate,2TBDMS,isomer #2	C=C(CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1765.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetylbutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-d74c72d28c30ba47007a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetylbutyrate GC-MS (1 TMS) - 70eV, Positive	splash10-0076-9300000000-2f4f5d82002d35670cb1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetylbutyrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 10V, Positive-QTOF	splash10-03dj-4900000000-06d2e7c20000d95cb762	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 20V, Positive-QTOF	splash10-03xs-9400000000-d502e3776bf8ee1dacf8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 40V, Positive-QTOF	splash10-0uxr-9000000000-c8dc2c5b57bc872311e4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 10V, Negative-QTOF	splash10-004i-1900000000-c8bc1ee45afd87b963f2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 20V, Negative-QTOF	splash10-06vr-6900000000-443256d51dd82e63bc96	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 40V, Negative-QTOF	splash10-0a4l-9000000000-263637adefeac595de6a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 10V, Negative-QTOF	splash10-01ri-6900000000-f5fb9cf43d60e2bdb1f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 20V, Negative-QTOF	splash10-0a4i-9000000000-6822ee7f89ce916c4f6b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 40V, Negative-QTOF	splash10-0a4l-9000000000-b5186cf0c530754526e0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 10V, Positive-QTOF	splash10-03dv-9300000000-04fbb62fc5704c241ad2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 20V, Positive-QTOF	splash10-0006-9000000000-7e2799bc14a0fef960c7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetylbutyrate 40V, Positive-QTOF	splash10-0006-9000000000-be67ec0679994457ee2c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected and Quantified	0.349 +/- 0.124 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.357 +/- 0.167 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.366 +/- 0.242 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.417 +/- 0.137 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.446 +/- 0.157 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.523 +/- 0.224 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02129

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18407

PDB ID

Not Available

ChEBI ID

15888

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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]

Showing metabocard for 4-Acetylbutyrate (HMDB0061881)

MOL for HMDB0061881 (4-Acetylbutyrate)

3D MOL for HMDB0061881 (4-Acetylbutyrate)

3D SDF for HMDB0061881 (4-Acetylbutyrate)

3D-SDF for HMDB0061881 (4-Acetylbutyrate)

PDB for HMDB0061881 (4-Acetylbutyrate)

3D PDB for HMDB0061881 (4-Acetylbutyrate)

SMILES for HMDB0061881 (4-Acetylbutyrate)

INCHI for HMDB0061881 (4-Acetylbutyrate)

Structure for HMDB0061881 (4-Acetylbutyrate)

3D Structure for HMDB0061881 (4-Acetylbutyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra