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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 03:04:17 UTC
Update Date2023-02-21 17:28:40 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 allyl methyl 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. Methyl 2-propenyl disulfide is an alliaceous, garlic, and green tasting compound. Methyl 2-propenyl disulfide is found, on average, in the highest concentration within soft-necked garlics (Allium sativum L. var. sativum). Methyl 2-propenyl disulfide has also been detected, but not quantified in, several different foods, such as allia (Allium), garden onions (Allium cepa), red onion, chives (Allium schoenoprasum), and welsh onions (Allium fistulosum). This could make methyl 2-propenyl disulfide a potential biomarker for the consumption of these foods. Methyl 2-propenyl disulfide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Methyl 2-propenyl disulfide.
Structure
Data?1677000519
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
Methyl 2-propenyl disulfideChEBI
2-PropenylmethyldisulfideHMDB
3-(Methyldisulfanyl)prop-1-eneHMDB
Disulfide, allyl methylHMDB
Disulfide, methyl 2-propenylHMDB
FEMA 3127HMDB
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point30.00 to 33.00 °C. @ 20.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP2.871 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.85931661259
DarkChem[M-H]-117.61631661259
DeepCCS[M+H]+126.87730932474
DeepCCS[M-H]-125.01530932474
DeepCCS[M-2H]-160.34930932474
DeepCCS[M+Na]+134.34230932474
AllCCS[M+H]+123.532859911
AllCCS[M+H-H2O]+119.332859911
AllCCS[M+NH4]+127.432859911
AllCCS[M+Na]+128.532859911
AllCCS[M-H]-136.632859911
AllCCS[M+Na-2H]-141.232859911
AllCCS[M+HCOO]-146.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl 2-propenyl disulfideCSSCC=C1254.5Standard polar33892256
Methyl 2-propenyl disulfideCSSCC=C889.6Standard non polar33892256
Methyl 2-propenyl disulfideCSSCC=C927.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl 2-propenyl disulfide EI-B (Non-derivatized)splash10-006x-9400000000-b22656c2fc50d291c4332017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 2-propenyl disulfide EI-B (Non-derivatized)splash10-006x-9400000000-b22656c2fc50d291c4332018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 2-propenyl disulfide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-3fa975297f7692e3fe542017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 2-propenyl disulfide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 2-propenyl disulfide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9400000000-856243b0edb1ecdb248c2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 10V, Positive-QTOFsplash10-00di-2900000000-e03c0f5ea97b029207c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 20V, Positive-QTOFsplash10-006x-9100000000-abe867e9c4013484ac4e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 40V, Positive-QTOFsplash10-0006-9000000000-e7405b22a930dc4a3b782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 10V, Negative-QTOFsplash10-014i-7900000000-a33d414c2259e6db34362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 20V, Negative-QTOFsplash10-00dm-9000000000-d315cbc5a8b4f1c41d662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 40V, Negative-QTOFsplash10-00di-9000000000-d7971f432840cb9b5c5d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 10V, Negative-QTOFsplash10-004m-9000000000-ef96b828ac069c1341a62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 20V, Negative-QTOFsplash10-0002-9000000000-b8ccb9f6306766cb8e142021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 40V, Negative-QTOFsplash10-004i-9000000000-1d58e6810a052e42af362021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 10V, Positive-QTOFsplash10-00b9-9000000000-9af83ce6d3c6853ffc902021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 20V, Positive-QTOFsplash10-00fr-9000000000-06ae20f4fc773ea950012021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 2-propenyl disulfide 40V, Positive-QTOFsplash10-000g-9000000000-78aa2b9636ad8c22c8062021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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 IDNot Available
Good Scents IDrw1009831
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.. .