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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:53 UTC
Update Date2019-07-23 06:08:57 UTC
HMDB IDHMDB0031529
Secondary Accession Numbers
  • HMDB31529
Metabolite Identification
Common Name3-Methyl-2-butene-1-thiol
Description3-Methyl-2-butene-1-thiol, also known as 4-mercapto-2-methyl-2-butene or dimethylallyl mercaptan, 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 extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methyl-2-butene-1-thiol is an amine, leek, and onion tasting compound. Outside of the human body, 3-Methyl-2-butene-1-thiol has been detected, but not quantified in, alcoholic beverages and coffee and coffee products. This could make 3-methyl-2-butene-1-thiol a potential biomarker for the consumption of these foods. Substance responsible for ''sun-struck'' flavour of beer.
Structure
Data?1563862137
Synonyms
ValueSource
3-Methyl-2-buten-1-thiolHMDB
3-Methyl-2-butenethiolHMDB
3-Methyl-but-2-ene-1-thiolHMDB
4-Mercapto-2-methyl-2-buteneHMDB
Dimethylallyl mercaptanHMDB
FEMA 3896HMDB
Prenyl mercaptanHMDB
PrenylthiolHMDB
3-Methyl-2-butene-1-thiolMeSH
Chemical FormulaC5H10S
Average Molecular Weight102.198
Monoisotopic Molecular Weight102.05032101
IUPAC Name3-methylbut-2-ene-1-thiol
Traditional Name3-methylbut-2-ene-1-thiol
CAS Registry Number5287-45-6
SMILES
CC(C)=CCS
InChI Identifier
InChI=1S/C5H10S/c1-5(2)3-4-6/h3,6H,4H2,1-2H3
InChI KeyGYDPOKGOQFTYGW-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.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiols
Sub ClassAlkylthiols
Direct ParentAlkylthiols
Alternative Parents
Substituents
  • Alkylthiol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Solubility3.17 g/LALOGPS
logP2.15ALOGPS
logP2.09ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)10ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.41 m³·mol⁻¹ChemAxon
Polarizability12.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9000000000-b8d68df2dd8ebd980ea6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3900000000-eb8cb9c86fc67e8f5fcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-9600000000-19cd0b9e0780a47978e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1003-9000000000-e0c5f1873d7ec6b848caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-9800000000-890a5f7f807914286b28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-9800000000-3367fcceec2f4f5d1d4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-c34255bbb1eff5caa337Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008136
KNApSAcK IDNot Available
Chemspider ID129292
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound146586
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .