Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Allyl isothiocyanate (HMDB05843)

Record Information
Version 3.5
Creation Date 2007-04-12 09:38:43 -0600
Update Date 2013-02-08 17:14:23 -0700
HMDB ID HMDB05843
Secondary Accession Numbers None
Metabolite Identification
Common Name Allyl isothiocyanate
Description Allyl 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 well soluble in most organic solvents. AITC possesses numerous biochemical and physiological activities. It is cytotoxic and tumorigenic at high doses and also is 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 Link_out, 8222057 Link_out, 8000299 Link_out, 10754276 Link_out, 15373848 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Propenyl isothiocyanate
  2. 3-Iso-Thiocyanatoprop-1-ene
  3. 3-Isothiocyanato-1-propene
  4. 3-Isothiocyanatoprop-1-ene
  5. AITC
  6. Allyl isosulfocyanate
  7. Allyl isosulphocyanate
  8. Allyl isothiocyanate (natural)
  9. Allyl isothiocyanate (usp)
  10. Allyl isothiocyanate non-perfume grade
  11. Allyl mustard oil
  12. Allyl sevenolum
  13. Allylisothiokyanat [czech]
  14. Allylsenevol
  15. Allylsenfoel
  16. Allylsevenolum
  17. Allyspol
  18. Artificial mustard oil
  19. Carbospol
  20. Caswell No. 027
  21. FEMA No. 2034
  22. Isothiocyanate D'allyle
  23. Isothiocyansaeureallylester
  24. Mustard oil
  25. Oil of mustard
  26. Oleum sinapis
  27. Oleum sinapis volatile
  28. Redskin
  29. Senfoel
  30. Synthetic mustard oil
  31. Volatile mustard oil
  32. Volatile oil of mustard
Chemical Formula C4H5NS
Average Molecular Weight 99.154
Monoisotopic Molecular Weight 99.014269855
IUPAC Name 3-isothiocyanatoprop-1-ene
Traditional IUPAC Name redskin
CAS Registry Number 57-06-7
SMILES C=CCN=C=S
InChI Identifier InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
InChI Key ZOJBYZNEUISWFT-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Isothiocyanates
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
Direct Parent Isothiocyanates
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -80 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2 mg/mL at 20 °C Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 1.90 ALOGPS
LogP 1.8 ChemAxon
LogS -2.49 ALOGPS
pKa (strongest basic) -3.9 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 12.36 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 30.49 ChemAxon
Polarizability 10.51 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80B)
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.14 +/- 0.098 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012440
KNApSAcK ID Not Available
Chemspider ID 21105854 Link_out
KEGG Compound ID C19317 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Allyl isothiocyanate Link_out
NuGOwiki Link HMDB05843 Link_out
Metagene Link HMDB05843 Link_out
METLIN ID Not Available
PubChem Compound 5971 Link_out
PDB ID Not Available
ChEBI ID 494804 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available