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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:51 UTC

Update Date

2023-02-21 17:21:50 UTC

HMDB ID

HMDB0032271

Secondary Accession Numbers

HMDB32271

Metabolite Identification

Common Name

Ethyl 3-mercaptobutyrate

Description

Ethyl 3-mercaptobutyrate 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 3-mercaptobutyrate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl 3-mercaptobutyric acid	Generator

Chemical Formula

C₆H₁₂O₂S

Average Molecular Weight

148.223

Monoisotopic Molecular Weight

148.055800318

IUPAC Name

ethyl 3-sulfanylbutanoate

Traditional Name

ethyl 3-sulfanylbutanoate

CAS Registry Number

156472-94-5

SMILES

CCOC(=O)CC(C)S

InChI Identifier

InChI=1S/C6H12O2S/c1-3-8-6(7)4-5(2)9/h5,9H,3-4H2,1-2H3

InChI Key

FPBCNQQYLDBWMH-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
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Alkylthiol
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

Physiological effect

Organoleptic effect

Odor

Roasted

Taste

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0032271)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032271)

Source

Endogenous

Endogenous (HMDB: HMDB0032271)

Animal

Animal (HMDB: HMDB0032271)

Exogenous

Food

Food (HMDB: HMDB0032271)

Exogenous (HMDB: HMDB0032271)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032271)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032271)

Lipid metabolism pathway (HMDB: HMDB0032271)

Cellular process

Cell signaling (HMDB: HMDB0032271)

Biochemical process

Lipid transport (HMDB: HMDB0032271)

Role

Biological role

Energy source (HMDB: HMDB0032271)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032271)

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	2.86 g/L	ALOGPS
logP	1.91	ALOGPS
logP	1.26	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	39.06 m³·mol⁻¹	ChemAxon
Polarizability	15.96 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.346	31661259
DarkChem	[M-H]-	128.345	31661259
DeepCCS	[M+H]+	137.384	30932474
DeepCCS	[M-H]-	134.91	30932474
DeepCCS	[M-2H]-	171.046	30932474
DeepCCS	[M+Na]+	146.268	30932474
AllCCS	[M+H]+	133.6	32859911
AllCCS	[M+H-H2O]+	129.7	32859911
AllCCS	[M+NH4]+	137.3	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	135.0	32859911
AllCCS	[M+Na-2H]-	138.0	32859911
AllCCS	[M+HCOO]-	141.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.56 minutes	32390414
Predicted by Siyang on May 30, 2022	14.2083 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.81 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2135.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	502.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	173.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	321.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	124.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	534.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	698.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	324.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1088.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	382.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1331.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	311.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	626.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	501.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	128.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 3-mercaptobutyrate	CCOC(=O)CC(C)S	1574.7	Standard polar	33892256
Ethyl 3-mercaptobutyrate	CCOC(=O)CC(C)S	1037.3	Standard non polar	33892256
Ethyl 3-mercaptobutyrate	CCOC(=O)CC(C)S	1063.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl 3-mercaptobutyrate,1TMS,isomer #1	CCOC(=O)CC(C)S[Si](C)(C)C	1246.7	Semi standard non polar	33892256
Ethyl 3-mercaptobutyrate,1TMS,isomer #1	CCOC(=O)CC(C)S[Si](C)(C)C	1304.2	Standard non polar	33892256
Ethyl 3-mercaptobutyrate,1TBDMS,isomer #1	CCOC(=O)CC(C)S[Si](C)(C)C(C)(C)C	1470.2	Semi standard non polar	33892256
Ethyl 3-mercaptobutyrate,1TBDMS,isomer #1	CCOC(=O)CC(C)S[Si](C)(C)C(C)(C)C	1526.6	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 3-mercaptobutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-9400000000-956059084afdf70c4036	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 3-mercaptobutyrate 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 3-mercaptobutyrate 10V, Positive-QTOF	splash10-0002-2900000000-b9f1f260db86906d1c4a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 20V, Positive-QTOF	splash10-0fr2-9800000000-5509fbe3057d8558fb0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 40V, Positive-QTOF	splash10-0ar3-9000000000-2ce8e2878aea5e702f0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 10V, Negative-QTOF	splash10-0002-3900000000-75d8b0a23ec4296d3b70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 20V, Negative-QTOF	splash10-0f6t-9800000000-0975189185c06b7adef7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 40V, Negative-QTOF	splash10-001j-9100000000-985715533a949af4cdda	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 10V, Positive-QTOF	splash10-0ir0-7900000000-0639cc245daf6bfee52e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 20V, Positive-QTOF	splash10-0j4i-9400000000-e31bf705e7d06c879784	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 40V, Positive-QTOF	splash10-01r7-9000000000-2b11fc3ec3a849bd9250	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 10V, Negative-QTOF	splash10-000b-9600000000-3fb46120c65668910d88	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 20V, Negative-QTOF	splash10-053r-9100000000-e7d5ffedb52b0eeb60c8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl 3-mercaptobutyrate 40V, Negative-QTOF	splash10-001i-9000000000-0c407334b15e2dec5bb7	2021-09-24	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+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

FDB009396

KNApSAcK ID

Not Available

Chemspider ID

8009717

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9833996

PDB ID

Not Available

ChEBI ID

Not Available

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 ]
(). 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 3-mercaptobutyrate (HMDB0032271)

MOL for HMDB0032271 (Ethyl 3-mercaptobutyrate)

3D MOL for HMDB0032271 (Ethyl 3-mercaptobutyrate)

3D SDF for HMDB0032271 (Ethyl 3-mercaptobutyrate)

3D-SDF for HMDB0032271 (Ethyl 3-mercaptobutyrate)

PDB for HMDB0032271 (Ethyl 3-mercaptobutyrate)

3D PDB for HMDB0032271 (Ethyl 3-mercaptobutyrate)

SMILES for HMDB0032271 (Ethyl 3-mercaptobutyrate)

INCHI for HMDB0032271 (Ethyl 3-mercaptobutyrate)

Structure for HMDB0032271 (Ethyl 3-mercaptobutyrate)

3D Structure for HMDB0032271 (Ethyl 3-mercaptobutyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra