Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 15:38:43 UTC
Update Date2021-10-13 04:47:38 UTC
HMDB IDHMDB0005843
Secondary Accession Numbers
  • HMDB05843
Metabolite Identification
Common NameAllyl isothiocyanate
DescriptionAllyl isothiocyanate is a volatile organic compound. Allyl isothiocyanate (AITC) is a constituent of mustard, horseradish and wasabi and certain vegetables found in the human diet, mostly in cruciferous vegetables. AITC is a colorless to pale yellow liquid that is slightly soluble in water, but soluble in most organic solvents. AITC possesses numerous biochemical and physiological activities. It is cytotoxic and tumorigenic at high doses and is also a modulator of enzymes involved in metabolism of xenobiotics, including carcinogens. It is plausible that the wide consumption of dietary AITC may have profound effects on human health. oxidative DNA damage may play important roles in carcinogenic processes induced by AITC. Allergic contact dermatitis from AICT is well known but infrequently reported. AITC is occasionally found as a volatile component of normal human biofluids. (PMID:5556886 , 8222057 , 8000299 , 10754276 , 15373848 ).
Structure
Data?1582752367
Synonyms
ValueSource
2-Propenyl isothiocyanateChEBI
3-Isothiocyanato-1-propeneChEBI
AITChEBI
AITCChEBI
Allyl isosulfocyanateChEBI
Allyl mustard oilChEBI
AllylsenfoelChEBI
Isothiocyanate d'allyleChEBI
Isothiocyanic acid allyl esterChEBI
Mustard oilChEBI
Oil OF mustardChEBI
Oleum sinapisChEBI
Senf oelChEBI
Volatile mustard oilChEBI
Volatile oil OF mustardChEBI
2-Propenyl isothiocyanic acidGenerator
Allyl isosulfocyanic acidGenerator
Allyl isosulphocyanateGenerator
Allyl isosulphocyanic acidGenerator
Isothiocyanic acid d'allyleGenerator
Isothiocyanate allyl esterGenerator
Allyl isothiocyanic acidGenerator
3-iso-Thiocyanatoprop-1-eneHMDB
3-Isothiocyanatoprop-1-eneHMDB
Allyl isothiocyanate (natural)HMDB
Allyl isothiocyanate non-perfume gradeHMDB
Allyl sevenolumHMDB
AllylsenevolHMDB, MeSH
AllylsevenolumHMDB
AllyspolHMDB
Artificial mustard oilHMDB
CarbospolHMDB
Caswell no. 027HMDB
FEMA no. 2034HMDB
IsothiocyansaeureallylesterHMDB
Oleum sinapis volatileHMDB
RedskinHMDB
SenfoelHMDB
Synthetic mustard oilHMDB
Chemical FormulaC4H5NS
Average Molecular Weight99.154
Monoisotopic Molecular Weight99.014269855
IUPAC Name3-isothiocyanatoprop-1-ene
Traditional Nameallyl isothiocyanate
CAS Registry Number57-06-7
SMILES
C=CCN=C=S
InChI Identifier
InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
InChI KeyZOJBYZNEUISWFT-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 Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-80 °CNot Available
Boiling Point150.00 to 152.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2 mg/mL at 20 °CNot Available
LogP2.150The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP1.9ALOGPS
logP1.8ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity30.49 m³·mol⁻¹ChemAxon
Polarizability10.51 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]+118.68531661259
DarkChem[M-H]-115.01131661259
DeepCCS[M+H]+124.3630932474
DeepCCS[M-H]-122.47230932474
DeepCCS[M-2H]-157.93630932474
DeepCCS[M+Na]+132.00230932474
AllCCS[M+H]+123.632859911
AllCCS[M+H-H2O]+119.232859911
AllCCS[M+NH4]+127.732859911
AllCCS[M+Na]+128.932859911
AllCCS[M-H]-130.132859911
AllCCS[M+Na-2H]-134.732859911
AllCCS[M+HCOO]-139.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Allyl isothiocyanateC=CCN=C=S1385.2Standard polar33892256
Allyl isothiocyanateC=CCN=C=S854.9Standard non polar33892256
Allyl isothiocyanateC=CCN=C=S874.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Allyl isothiocyanate EI-B (Non-derivatized)splash10-000e-9000000000-74e6764518eaef9083ea2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Allyl isothiocyanate EI-B (Non-derivatized)splash10-000e-9000000000-74e6764518eaef9083ea2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Allyl isothiocyanate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-e5da626a3f0a9112da7f2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Allyl isothiocyanate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000e-9000000000-69a4920e3d464262cd5f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Allyl isothiocyanate Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0005-9000000000-52a42150ed565c57dd632012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Allyl isothiocyanate Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00kf-9000000000-f39db8b3315f05512c4e2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Allyl isothiocyanate Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000l-9000000000-fd8f23ba9a99d3b95b602012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Allyl isothiocyanate EI-B (HITACHI M-80B) , Positive-QTOFsplash10-000e-9000000000-c10457306477602160fd2012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 10V, Positive-QTOFsplash10-0udi-3900000000-6f00e6c8cbe246d39e052017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 20V, Positive-QTOFsplash10-0006-9300000000-dc72ed6e7c7c177d9abf2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 40V, Positive-QTOFsplash10-0006-9000000000-ccb9e34efa3fbf3caebb2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 10V, Negative-QTOFsplash10-0002-9000000000-a31fab83b72890b37d9e2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 20V, Negative-QTOFsplash10-052b-9000000000-ac309b871ff92649f3d12017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 40V, Negative-QTOFsplash10-0a4i-9000000000-6a8f7896b2956a540af42017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 10V, Positive-QTOFsplash10-0udi-6900000000-c391badfd4188e78a8222021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 20V, Positive-QTOFsplash10-0a4i-9100000000-87228e1d22765d017b752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 40V, Positive-QTOFsplash10-0a4r-9000000000-605088af9052853999962021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 10V, Negative-QTOFsplash10-0a4i-9000000000-9aace16230ba7be259d52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 20V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allyl isothiocyanate 40V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.14 +/- 0.098 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012440
KNApSAcK IDNot Available
Chemspider ID21105854
KEGG Compound IDC19317
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllyl_isothiocyanate
METLIN IDNot Available
PubChem Compound5971
PDB IDNot Available
ChEBI ID73224
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1002981
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. Jiao D, Ho CT, Foiles P, Chung FL: Identification and quantification of the N-acetylcysteine conjugate of allyl isothiocyanate in human urine after ingestion of mustard. Cancer Epidemiol Biomarkers Prev. 1994 Sep;3(6):487-92. [PubMed:8000299 ]
  3. Musk SR, Johnson IT: Allyl isothiocyanate is selectively toxic to transformed cells of the human colorectal tumour line HT29. Carcinogenesis. 1993 Oct;14(10):2079-83. [PubMed:8222057 ]
  4. Murata M, Yamashita N, Inoue S, Kawanishi S: Mechanism of oxidative DNA damage induced by carcinogenic allyl isothiocyanate. Free Radic Biol Med. 2000 Mar 1;28(5):797-805. [PubMed:10754276 ]
  5. Lerbaek A, Rastogi SC, Menne T: Allergic contact dermatitis from allyl isothiocyanate in a Danish cohort of 259 selected patients. Contact Dermatitis. 2004 Aug;51(2):79-83. [PubMed:15373848 ]