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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:47 UTC

Update Date

2023-02-21 17:21:48 UTC

HMDB ID

HMDB0032259

Secondary Accession Numbers

HMDB32259

Metabolite Identification

Common Name

Ethyl 4-(acetylthio)butyrate

Description

Ethyl 4-(acetylthio)butyrate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a small amount of articles have been published on Ethyl 4-(acetylthio)butyrate.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -8.057  -4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.946  -3.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.724  -3.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.389  -3.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.723  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.055  -4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.612  -4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.612  -5.541   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.056  -1.691   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -5.390  -4.001   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0       1.278  -3.231   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    7                                                            
CONECT    3    1   11                                                       
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    4   12                                                       
CONECT    7    2    9   12                                                  
CONECT    8    5   10   11                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    3    8                                                       
CONECT   12    6    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl 4-(acetylthio)butyric acid	Generator

Chemical Formula

C₈H₁₄O₃S

Average Molecular Weight

190.26

Monoisotopic Molecular Weight

190.066365004

IUPAC Name

ethyl 4-(acetylsulfanyl)butanoate

Traditional Name

ethyl 4-(acetylsulfanyl)butanoate

CAS Registry Number

104228-51-5

SMILES

CCOC(=O)CCCSC(C)=O

InChI Identifier

InChI=1S/C8H14O3S/c1-3-11-8(10)5-4-6-12-7(2)9/h3-6H2,1-2H3

InChI Key

AKUUBUQNHOTPHG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Carbothioic s-ester
Thiocarboxylic acid ester
Carboxylic acid ester
Sulfenyl compound
Thiocarboxylic acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0032259)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032259)

Source

Endogenous

Endogenous (HMDB: HMDB0032259)

Animal

Animal (HMDB: HMDB0032259)

Exogenous

Food

Food (HMDB: HMDB0032259)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032259)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032259)

Cellular process

Cell signaling (HMDB: HMDB0032259)

Biochemical process

Lipid transport (HMDB: HMDB0032259)

Role

Biological role

Energy storage (HMDB: HMDB0032259)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032259)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	262.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4300 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.671 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.35 g/L	ALOGPS
logP	1.47	ALOGPS
logP	1.08	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	48.81 m³·mol⁻¹	ChemAxon
Polarizability	20.59 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	143.08	31661259
DarkChem	[M-H]-	138.85	31661259
DeepCCS	[M+H]+	143.913	30932474
DeepCCS	[M-H]-	140.223	30932474
DeepCCS	[M-2H]-	177.398	30932474
DeepCCS	[M+Na]+	152.855	30932474
AllCCS	[M+H]+	142.0	32859911
AllCCS	[M+H-H2O]+	138.5	32859911
AllCCS	[M+NH4]+	145.4	32859911
AllCCS	[M+Na]+	146.3	32859911
AllCCS	[M-H]-	144.6	32859911
AllCCS	[M+Na-2H]-	146.4	32859911
AllCCS	[M+HCOO]-	148.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 4-(acetylthio)butyrate	CCOC(=O)CCCSC(C)=O	2185.1	Standard polar	33892256
Ethyl 4-(acetylthio)butyrate	CCOC(=O)CCCSC(C)=O	1401.0	Standard non polar	33892256
Ethyl 4-(acetylthio)butyrate	CCOC(=O)CCCSC(C)=O	1406.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 4-(acetylthio)butyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-9600000000-8ee4d0e23bc33dedacca	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 4-(acetylthio)butyrate 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 - Ethyl 4-(acetylthio)butyrate 10V, Positive-QTOF	splash10-0005-1900000000-29a95ef1949bb44970d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 20V, Positive-QTOF	splash10-0fr2-7900000000-35323a9cdb6c45dde0f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 40V, Positive-QTOF	splash10-054o-9000000000-6626611fcfdc852806cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 10V, Negative-QTOF	splash10-000e-1900000000-8104e03c4efd0b77c311	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 20V, Negative-QTOF	splash10-0007-5900000000-9f01e6b45885e84289ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 40V, Negative-QTOF	splash10-0006-9200000000-d74c1fd85b8e079176e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 10V, Negative-QTOF	splash10-000i-1900000000-41b14b37d738c9f7f3db	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 20V, Negative-QTOF	splash10-00dl-9300000000-c1c0ef27964e006839a6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 40V, Negative-QTOF	splash10-00di-9100000000-a166d30d08701c159a28	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 10V, Positive-QTOF	splash10-0006-8900000000-82968be9bb907135c07a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 20V, Positive-QTOF	splash10-00rj-9100000000-2473419e5506b85890ef	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 4-(acetylthio)butyrate 40V, Positive-QTOF	splash10-00di-9000000000-264173285293ce6adcc7	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB009372

KNApSAcK ID

Not Available

Chemspider ID

21105893

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54048924

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1584281

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 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Ethyl 4-(acetylthio)butyrate (HMDB0032259)

MOL for HMDB0032259 (Ethyl 4-(acetylthio)butyrate)

3D MOL for HMDB0032259 (Ethyl 4-(acetylthio)butyrate)

3D SDF for HMDB0032259 (Ethyl 4-(acetylthio)butyrate)

3D-SDF for HMDB0032259 (Ethyl 4-(acetylthio)butyrate)

PDB for HMDB0032259 (Ethyl 4-(acetylthio)butyrate)

3D PDB for HMDB0032259 (Ethyl 4-(acetylthio)butyrate)

SMILES for HMDB0032259 (Ethyl 4-(acetylthio)butyrate)

INCHI for HMDB0032259 (Ethyl 4-(acetylthio)butyrate)

Structure for HMDB0032259 (Ethyl 4-(acetylthio)butyrate)

3D Structure for HMDB0032259 (Ethyl 4-(acetylthio)butyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra