CHEBI:351346 - phenethyl isothiocyanate

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ChEBI Name phenethyl isothiocyanate
ChEBI ID CHEBI:351346
Definition An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine nucleobase and the other, nicotinamide. NAD exists in two forms: an oxidized and reduced form, abbreviated as NAD+ and NADH (H for hydrogen), respectively. In cellular metabolism, NAD is involved in redox reactions, carrying electrons from one reaction to another, so it is found in two forms: NAD+ is an oxidizing agent, accepting electrons from other molecules and becoming reduced; with H+, this reaction forms NADH, which can be used as a reducing agent to donate electrons. These electron transfer reactions are the main function of NAD. It is also used in other cellular processes, most notably as a substrate of enzymes in adding or removing chemical groups to or from proteins, in posttranslational modifications. Because of the importance of these functions, the enzymes involved in NAD metabolism are targets for drug discovery. In organisms, NAD can be synthesized from simple building-blocks (de novo) from either tryptophan or aspartic acid, each a case of an amino acid. Alternatively, more complex components of the coenzymes are taken up from nutritive compounds such as nicotinic acid; similar compounds are produced by reactions that break down the structure of NAD, providing a salvage pathway that recycles them back into their respective active form. Some NAD is converted into the coenzyme nicotinamide adenine dinucleotide phosphate (NADP), whose chemistry largely parallels that of NAD, though its predominant role is as a coenzyme in anabolic metabolism. In the name NAD+, the superscripted plus sign indicates the positive formal charge on one of its nitrogen atoms. A biological coenzyme that acts as an electron carrier in enzymatic reactions. NADP is a reducing agent in anabolic reactions like the Calvin cycle and lipid and nucleic acid syntheses. NADP exists in two forms: NADP+, the oxidized form, and NADPH, the reduced form. NADP is similar to nicotinamide adenine dinucleotide (NAD), but NADP has a phosphate group at the C-2′ position of the adenosyl.
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Formula C9H9NS
Net Charge 0
Average Mass 163.23900
Monoisotopic Mass 163.04557
InChI InChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
InChIKey IZJDOKYDEWTZSO-UHFFFAOYSA-N
SMILES S=C=NCCc1ccccc1
Roles Classification
Biological Role(s): EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor
An EC 1.2.1.* (oxidoreductase acting on donor aldehyde/oxo group with NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of aldehyde dehydrogenase (NAD+), EC 1.2.1.3.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing phenethyl isothiocyanate (CHEBI:351346) has role antineoplastic agent (CHEBI:35610)
phenethyl isothiocyanate (CHEBI:351346) has role EC 1.2.1.3 [aldehyde dehydrogenase (NAD+)] inhibitor (CHEBI:35487)
phenethyl isothiocyanate (CHEBI:351346) has role metabolite (CHEBI:25212)
phenethyl isothiocyanate (CHEBI:351346) is a isothiocyanate (CHEBI:52221)
Incoming S-[(2-phenylethyl)carbamothioyl]glutathione (CHEBI:136426) has functional parent phenethyl isothiocyanate (CHEBI:351346)
IUPAC Name
(2-isothiocyanatoethyl)benzene
Synonyms Sources
(2-Isothiocyanatoethyl)benzene NIST Chemistry WebBook
2-Phenylethyl isothiocyanate ChemIDplus
β-phenethyl isothiocyanate NIST Chemistry WebBook
β-phenylethyl isothiocyanate NIST Chemistry WebBook
PEITC ChEBI
Phenethyl mustard oil ChemIDplus
Phenyläthylsenföl ChemIDplus
Phenylethyl isothiocyanate ChemIDplus
Manual Xrefs Databases
LSM-4926 LINCS
Phenethyl_isothiocyanate Wikipedia
View more database links
Registry Numbers Types Sources
2084162 Reaxys Registry Number Reaxys
2257-09-2 CAS Registry Number ChemIDplus
2257-09-2 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations
Last Modified
06 March 2017