CHEBI:74571 - iodoacetic acid

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ChEBI Name iodoacetic acid
ChEBI ID CHEBI:74571
Definition A haloacetic acid that is acetic acid in which one of the hydrogens of the methyl group is replaced by an iodine atom.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C2H3IO2
Net Charge 0
Average Mass 185.94850
Monoisotopic Mass 185.918
InChI InChI=1S/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5)
InChIKey JDNTWHVOXJZDSN-UHFFFAOYSA-N
SMILES OC(=O)CI
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): alkylating agent
Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
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ChEBI Ontology
Outgoing iodoacetic acid (CHEBI:74571) has role alkylating agent (CHEBI:22333)
iodoacetic acid (CHEBI:74571) is a haloacetic acid (CHEBI:16277)
iodoacetic acid (CHEBI:74571) is a organoiodine compound (CHEBI:37142)
IUPAC Name
iodoacetic acid
Synonyms Sources
2-iodoacetic acid ChEBI
CH2ICO2H ChEBI
CH2ICOOH ChEBI
ICH2CO2H ChEBI
ICH2COOH ChEBI
iodoethanoic acid LIPID MAPS
monoiodoacetic acid ChemIDplus
Manual Xrefs Databases
Iodoacetic_acid Wikipedia
LMFA01090135 LIPID MAPS
LSM-5944 LINCS
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Registry Numbers Types Sources
1739079 Reaxys Registry Number Reaxys
64-69-7 CAS Registry Number ChemIDplus
64-69-7 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
21740901 PubMed citation Europe PMC
22206935 PubMed citation Europe PMC
22251455 PubMed citation Europe PMC
22562395 PubMed citation Europe PMC
23613747 PubMed citation Europe PMC
23641915 PubMed citation Europe PMC
23657794 PubMed citation Europe PMC
Last Modified
25 February 2016