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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:53 UTC

Update Date

2023-02-21 17:20:45 UTC

HMDB ID

HMDB0031529

Secondary Accession Numbers

HMDB31529

Metabolite Identification

Common Name

3-Methyl-2-butene-1-thiol

Description

3-Methyl-2-butene-1-thiol belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain. 3-Methyl-2-butene-1-thiol is an amine, leek, and onion tasting compound. 3-Methyl-2-butene-1-thiol has been detected, but not quantified in, several different foods, such as alcoholic beverages, arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 3-methyl-2-butene-1-thiol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Methyl-2-butene-1-thiol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methyl-2-buten-1-thiol	HMDB
3-Methyl-2-butenethiol	HMDB
3-Methyl-but-2-ene-1-thiol	HMDB
4-mercapto-2-Methyl-2-butene	HMDB
Dimethylallyl mercaptan	HMDB
FEMA 3896	HMDB
Prenyl mercaptan	HMDB
Prenylthiol	HMDB
3-Methyl-2-butene-1-thiol	MeSH

Chemical Formula

C₅H₁₀S

Average Molecular Weight

102.198

Monoisotopic Molecular Weight

102.05032101

IUPAC Name

3-methylbut-2-ene-1-thiol

Traditional Name

3-methylbut-2-ene-1-thiol

CAS Registry Number

5287-45-6

SMILES

CC(C)=CCS

InChI Identifier

InChI=1S/C5H10S/c1-5(2)3-4-6/h3,6H,4H2,1-2H3

InChI Key

GYDPOKGOQFTYGW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thiols

Sub Class

Alkylthiols

Direct Parent

Alkylthiols

Alternative Parents

Hydrocarbon derivatives

Substituents

Alkylthiol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031529)

Source

Endogenous

Endogenous (HMDB: HMDB0031529)

Plant

Coffea (HMDB: HMDB0031529)

Exogenous

Food

Food (HMDB: HMDB0031529)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0031529)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0031529)

Role

Biological role

Energy source (HMDB: HMDB0031529)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031529)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	128.00 to 135.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	718.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.528 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.17 g/L	ALOGPS
logP	2.15	ALOGPS
logP	2.09	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	10	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	33.41 m³·mol⁻¹	ChemAxon
Polarizability	12.5 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]+	120.27	31661259
DarkChem	[M-H]-	114.234	31661259
DeepCCS	[M+H]+	125.846	30932474
DeepCCS	[M-H]-	123.842	30932474
DeepCCS	[M-2H]-	159.367	30932474
DeepCCS	[M+Na]+	133.666	30932474
AllCCS	[M+H]+	121.6	32859911
AllCCS	[M+H-H2O]+	117.2	32859911
AllCCS	[M+NH4]+	125.7	32859911
AllCCS	[M+Na]+	126.8	32859911
AllCCS	[M-H]-	129.9	32859911
AllCCS	[M+Na-2H]-	134.5	32859911
AllCCS	[M+HCOO]-	139.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-2-butene-1-thiol	CC(C)=CCS	1094.7	Standard polar	33892256
3-Methyl-2-butene-1-thiol	CC(C)=CCS	792.8	Standard non polar	33892256
3-Methyl-2-butene-1-thiol	CC(C)=CCS	823.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-2-butene-1-thiol,1TMS,isomer #1	CC(C)=CCS[Si](C)(C)C	1075.0	Semi standard non polar	33892256
3-Methyl-2-butene-1-thiol,1TMS,isomer #1	CC(C)=CCS[Si](C)(C)C	1041.5	Standard non polar	33892256
3-Methyl-2-butene-1-thiol,1TBDMS,isomer #1	CC(C)=CCS[Si](C)(C)C(C)(C)C	1289.9	Semi standard non polar	33892256
3-Methyl-2-butene-1-thiol,1TBDMS,isomer #1	CC(C)=CCS[Si](C)(C)C(C)(C)C	1250.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-butene-1-thiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-9000000000-b8d68df2dd8ebd980ea6	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-butene-1-thiol 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 - 3-Methyl-2-butene-1-thiol 10V, Positive-QTOF	splash10-0udi-3900000000-eb8cb9c86fc67e8f5fcf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 20V, Positive-QTOF	splash10-0uxr-9600000000-19cd0b9e0780a47978e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 40V, Positive-QTOF	splash10-1003-9000000000-e0c5f1873d7ec6b848ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 10V, Negative-QTOF	splash10-0uxr-9800000000-890a5f7f807914286b28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 20V, Negative-QTOF	splash10-0udi-9800000000-3367fcceec2f4f5d1d4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 40V, Negative-QTOF	splash10-001i-9000000000-c34255bbb1eff5caa337	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 10V, Positive-QTOF	splash10-014i-9200000000-7ca2e2efb4dd1a30d697	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 20V, Positive-QTOF	splash10-014i-9000000000-b27ca0a4c7da29116624	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 40V, Positive-QTOF	splash10-0006-9000000000-38cfec5c59e93aa995f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 10V, Negative-QTOF	splash10-0ue9-8900000000-90b59f0c59afcdc4635c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 20V, Negative-QTOF	splash10-001i-9000000000-942ac689538269d6ca7b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-butene-1-thiol 40V, Negative-QTOF	splash10-001i-9000000000-942ac689538269d6ca7b	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)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

FDB008136

KNApSAcK ID

Not Available

Chemspider ID

129292

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146586

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1056341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3-Methyl-2-butene-1-thiol (HMDB0031529)

MOL for HMDB0031529 (3-Methyl-2-butene-1-thiol)

3D MOL for HMDB0031529 (3-Methyl-2-butene-1-thiol)

3D SDF for HMDB0031529 (3-Methyl-2-butene-1-thiol)

3D-SDF for HMDB0031529 (3-Methyl-2-butene-1-thiol)

PDB for HMDB0031529 (3-Methyl-2-butene-1-thiol)

3D PDB for HMDB0031529 (3-Methyl-2-butene-1-thiol)

SMILES for HMDB0031529 (3-Methyl-2-butene-1-thiol)

INCHI for HMDB0031529 (3-Methyl-2-butene-1-thiol)

Structure for HMDB0031529 (3-Methyl-2-butene-1-thiol)

3D Structure for HMDB0031529 (3-Methyl-2-butene-1-thiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra