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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-12 03:04:17 UTC
Update Date2019-07-23 06:34:18 UTC
HMDB IDHMDB0041389
Secondary Accession Numbers
  • HMDB41389
Metabolite Identification
Common NameMethyl 2-propenyl disulfide
DescriptionMethyl 2-propenyl disulfide, also known as 3-(methyldisulfanyl)-1-propene or methyl allyl disulphide, belongs to the class of organic compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS. An organic disulfide having allyl and methyl as the two organic groups. Methyl 2-propenyl disulfide is possibly neutral. Methyl 2-propenyl disulfide is an alliaceous, garlic, and green tasting compound. Outside of the human body, Methyl 2-propenyl disulfide is found, on average, in the highest concentration within soft-necked garlics. Methyl 2-propenyl disulfide has also been detected, but not quantified in, several different foods, such as allium (onion), chives, garden onions, and onion-family vegetables. This could make methyl 2-propenyl disulfide a potential biomarker for the consumption of these foods.
Structure
Data?1563863658
Synonyms
ValueSource
3-(Methyldisulfanyl)-1-propeneChEBI
3-(Methyldithio)prop-1-eneChEBI
4,5-Dithia-1-hexeneChEBI
Allyl methyl disulphideChEBI
Methyl allyl disulfideChEBI
Methylallyl disulphideChEBI
Allyl methyl disulfideKegg
3-(Methyldisulphanyl)-1-propeneGenerator
Methyl allyl disulphideGenerator
Methylallyl disulfideGenerator
Methyl 2-propenyl disulphideGenerator
2-PropenylmethyldisulfideHMDB
3-(Methyldisulfanyl)prop-1-eneHMDB
Disulfide, allyl methylHMDB
Disulfide, methyl 2-propenylHMDB
FEMA 3127HMDB
Methyl 2-propenyl disulfideChEBI
Chemical FormulaC4H8S2
Average Molecular Weight120.236
Monoisotopic Molecular Weight120.006741636
IUPAC Name3-(methyldisulfanyl)prop-1-ene
Traditional Nameallyl methyl disulfide
CAS Registry Number2179-58-0
SMILES
CSSCC=C
InChI Identifier
InChI=1S/C4H8S2/c1-3-4-6-5-2/h3H,1,4H2,2H3
InChI KeyXNZOTQPMYMCTBZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassAllyl sulfur compounds
Sub ClassNot Available
Direct ParentAllyl sulfur compounds
Alternative Parents
Substituents
  • Allyl sulfur compound
  • Dialkyldisulfide
  • Organic disulfide
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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 Solubility0.66 g/LALOGPS
logP1.82ALOGPS
logP2.06ChemAxon
logS-2.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.28 m³·mol⁻¹ChemAxon
Polarizability13 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)splash10-006x-9400000000-b22656c2fc50d291c433Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9400000000-b22656c2fc50d291c433Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-3fa975297f7692e3fe54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-e03c0f5ea97b029207c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9100000000-abe867e9c4013484ac4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-e7405b22a930dc4a3b78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-7900000000-a33d414c2259e6db3436Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dm-9000000000-d315cbc5a8b4f1c41d66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-d7971f432840cb9b5c5dSpectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9400000000-856243b0edb1ecdb248cSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Ulcerative colitis
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021321
KNApSAcK IDC00001257
Chemspider ID56217
KEGG Compound IDC08383
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62434
PDB IDNot Available
ChEBI ID6854
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.. .