CHEBI:73224 - allyl isothiocyanate

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ChEBI Name allyl isothiocyanate
ChEBI ID CHEBI:73224
Definition An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152°C, it is responsible for the pungent taste of mustard, horseradish, and wasabi.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Steve Jupe
Supplier Information No supplier information found for this compound.
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Retinal (also known as retinaldehyde) is a polyene chromophore. Retinal, bound to proteins called opsins, is the chemical basis of visual phototransduction, the light-detection stage of visual perception (vision). Some microorganisms use retinal to convert light into metabolic energy. One study suggests that approximately three billion years ago, most living organisms on Earth used retinal, rather than chlorophyll, to convert sunlight into energy. Because retinal absorbs mostly green light and transmits purple light, this gave rise to the Purple Earth hypothesis. Retinal itself is considered to be a form of vitamin A when eaten by an animal. There are many forms of vitamin A, all of which are converted to retinal, which cannot be made without them. The number of different molecules that can be converted to retinal varies from species to species. Retinal was originally called retinene, and was renamed after it was discovered to be vitamin A aldehyde. Vertebrate animals ingest retinal directly from meat, or they produce retinal from carotenoids – either from α-carotene or β-carotene – both of which are carotenes. They also produce it from β-cryptoxanthin, a type of xanthophyll. These carotenoids must be obtained from plants or other photosynthetic organisms. No other carotenoids can be converted by animals to retinal. Some carnivores cannot convert any carotenoids at all. The other main forms of vitamin A – retinol and a partially active form, retinoic acid – may both be produced from retinal. Invertebrates such as insects and squid use hydroxylated forms of retinal in their visual systems, which derive from conversion from other xanthophylls.
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Formula C4H5NS
Net Charge 0
Average Mass 99.15400
Monoisotopic Mass 99.01427
InChI InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
InChIKey ZOJBYZNEUISWFT-UHFFFAOYSA-N
SMILES C=CCN=C=S
Roles Classification
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
lachrymator
Any substance that stimulates the corneal nerves in the eves to cause tears.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing allyl isothiocyanate (CHEBI:73224) has role antimicrobial agent (CHEBI:33281)
allyl isothiocyanate (CHEBI:73224) has role antineoplastic agent (CHEBI:35610)
allyl isothiocyanate (CHEBI:73224) has role apoptosis inducer (CHEBI:68495)
allyl isothiocyanate (CHEBI:73224) has role lachrymator (CHEBI:74136)
allyl isothiocyanate (CHEBI:73224) has role metabolite (CHEBI:25212)
allyl isothiocyanate (CHEBI:73224) is a alkenyl isothiocyanate (CHEBI:183102)
allyl isothiocyanate (CHEBI:73224) is a isothiocyanate (CHEBI:52221)
IUPAC Name
3-isothiocyanatoprop-1-ene
Synonyms Sources
2-propenyl isothiocyanate ChemIDplus
3-isothiocyanato-1-propene ChemIDplus
3-Isothiocyanato-1-propene SUBMITTER
AIT ChEBI
AITC ChemIDplus
allyl isosulfocyanate ChemIDplus
allyl isothiocyanate UniProt
allyl mustard oil ChemIDplus
Allylsenfoel ChemIDplus
isothiocyanate d'allyle ChemIDplus
isothiocyanic acid allyl ester ChemIDplus
Mustard oil SUBMITTER
oil of mustard ChemIDplus
oleum sinapis ChemIDplus
Senf oel ChemIDplus
volatile mustard oil ChemIDplus
volatile oil of mustard ChemIDplus
Manual Xrefs Databases
Allyl_isothiocyanate Wikipedia
C19317 KEGG COMPOUND
D02818 KEGG DRUG
D02818 KEGG DRUG
HMDB0005843 HMDB
View more database links
Registry Numbers Types Sources
57-06-7 CAS Registry Number ChemIDplus
57-06-7 CAS Registry Number NIST Chemistry WebBook
773748 Reaxys Registry Number Reaxys
Citations Types Sources
20174640 PubMed citation Europe PMC
21237300 PubMed citation Europe PMC
21711355 PubMed citation Europe PMC
22093285 PubMed citation Europe PMC
22104119 PubMed citation Europe PMC
22131350 PubMed citation Europe PMC
22265303 PubMed citation Europe PMC
23008020 PubMed citation Europe PMC
23072699 PubMed citation Europe PMC
23212023 PubMed citation Europe PMC
23470258 PubMed citation Europe PMC
23535540 PubMed citation Europe PMC
23757176 PubMed citation Europe PMC
Last Modified
27 October 2021