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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:38:26 UTC
Update Date2019-07-23 06:14:33 UTC
HMDB IDHMDB0033867
Secondary Accession Numbers
  • HMDB33867
Metabolite Identification
Common Name4-Isothiocyanato-1-butene
Description4-Isothiocyanato-1-butene, also known as 1-butene 4-isothiocyanate or crotonyl mustard oil, belongs to the class of organic compounds known as isothiocyanates. These are organic compounds containing the isothiocyanate group, an isocyanate analogue with the general formula RN=C=S. 4-Isothiocyanato-1-butene is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Isothiocyanato-1-butene is an aromatic and pungent tasting compound. Outside of the human body, 4-Isothiocyanato-1-butene has been detected, but not quantified in, several different foods, such as brassicas, cabbages, cauliflowers, horseradish, and white cabbages. This could make 4-isothiocyanato-1-butene a potential biomarker for the consumption of these foods.
Structure
Data?1563862473
Synonyms
ValueSource
1-Butene 4-isothiocyanateHMDB
1-Butene-4-isothiocyanateHMDB
3-Butenyl isothiocyanateHMDB
But-3-enyl isothiocyanateHMDB
Crotonyl mustard oilHMDB
Crotyl mustard oilHMDB
Isothiocyanic acid, 3-butenyl esterHMDB
BylITCHMDB
ButenylisothiocyanateHMDB
Chemical FormulaC5H7NS
Average Molecular Weight113.181
Monoisotopic Molecular Weight113.029919919
IUPAC Name4-isothiocyanatobut-1-ene
Traditional Name1-butene, 4-isothiocyanato-
CAS Registry Number3386-97-8
SMILES
C=CCCN=C=S
InChI Identifier
InChI=1S/C5H7NS/c1-2-3-4-6-5-7/h2H,1,3-4H2
InChI KeySKIHGKNFJKJXPX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isothiocyanates. These are organic compounds containing the isothiocyanate group, an isocyanate analogue with the general formula RN=C=S.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassIsothiocyanates
Sub ClassNot Available
Direct ParentIsothiocyanates
Alternative Parents
Substituents
  • Isothiocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.46 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.41ALOGPS
logP2.09ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.25 m³·mol⁻¹ChemAxon
Polarizability12.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-9200000000-1a40200ada4e3470682dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-9200000000-1a40200ada4e3470682dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bf-9000000000-8f560f490ac3ff773e2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5900000000-6b5a0c36ac97abfbfafdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200000000-107fe6a8c4c497549b8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a06462555fc1d0881d1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-2fd61d6aae4db1e2552bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-9400000000-b269adb37f1cf3ae532bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-ab47c48091b0e907f16eSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FoodDB IDFDB012051
KNApSAcK IDNot Available
Chemspider ID69373
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76922
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .