CHEBI:131461 - 3-bromopyruvic acid

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ChEBI Name 3-bromopyruvic acid
ChEBI ID CHEBI:131461
Definition A 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is replaced by bromine. Synthetic brominated derivative and structural analog of pyruvic acid. Highly reactive alkylating agent. Anti-cancer drug
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Rob Nash
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Formula C3H3BrO3
Net Charge 0
Average Mass 166.958
Monoisotopic Mass 165.927
InChI InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
InChIKey PRRZDZJYSJLDBS-UHFFFAOYSA-N
SMILES C(O)(C(=O)CBr)=O
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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 3-bromopyruvic acid (CHEBI:131461) has functional parent pyruvic acid (CHEBI:32816)
3-bromopyruvic acid (CHEBI:131461) has role alkylating agent (CHEBI:22333)
3-bromopyruvic acid (CHEBI:131461) has role antineoplastic agent (CHEBI:35610)
3-bromopyruvic acid (CHEBI:131461) is a 2-oxo monocarboxylic acid (CHEBI:35910)
3-bromopyruvic acid (CHEBI:131461) is a organobromine compound (CHEBI:37141)
3-bromopyruvic acid (CHEBI:131461) is conjugate acid of 3-bromopyruvate (CHEBI:131592)
Incoming 3-bromopyruvate (CHEBI:131592) is conjugate base of 3-bromopyruvic acid (CHEBI:131461)
IUPAC Name
3-bromo-2-oxopropanoic acid
Synonyms Sources
3-BP SUBMITTER
3-Bromopyruvate ChemIDplus
bromopyruvate SUBMITTER
bromopyruvic acid SUBMITTER
Manual Xrefs Databases
3-BROMOPYRUVATE MetaCyc
Bromopyruvic_acid Wikipedia
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Registry Numbers Types Sources
1113-59-3 CAS Registry Number ChemIDplus
1746786 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
26053972 PubMed citation Europe PMC
26530887 PubMed citation Europe PMC
26708213 PubMed citation Europe PMC
26715289 PubMed citation Europe PMC
26740252 PubMed citation Europe PMC
26815411 PubMed citation Europe PMC
26825851 PubMed citation Europe PMC
26862728 PubMed citation Europe PMC
26922560 PubMed citation Europe PMC
Last Modified
21 March 2016