CHEBI:15344 - acetoacetic acid

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ChEBI Name acetoacetic acid
ChEBI ID CHEBI:15344
Definition A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40507, CHEBI:2391, CHEBI:22172
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Formula C4H6O3
Net Charge 0
Average Mass 102.08864
Monoisotopic Mass 102.032
InChI InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
InChIKey WDJHALXBUFZDSR-UHFFFAOYSA-N
SMILES CC(=O)CC(O)=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): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via ketone body )
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
(via ketone body )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing acetoacetic acid (CHEBI:15344) has functional parent butyric acid (CHEBI:30772)
acetoacetic acid (CHEBI:15344) has role metabolite (CHEBI:25212)
acetoacetic acid (CHEBI:15344) is a 3-oxo fatty acid (CHEBI:134416)
acetoacetic acid (CHEBI:15344) is a ketone body (CHEBI:73693)
acetoacetic acid (CHEBI:15344) is conjugate acid of acetoacetate (CHEBI:13705)
acetoacetic acid (CHEBI:15344) is tautomer of 3-hydroxy-3-butenoic acid (CHEBI:131367)
Incoming (R)-acetoacetylcarnitine (CHEBI:84841) has functional parent acetoacetic acid (CHEBI:15344)
2-methylacetoacetic acid (CHEBI:37079) has functional parent acetoacetic acid (CHEBI:15344)
acetoacetamide (CHEBI:28515) has functional parent acetoacetic acid (CHEBI:15344)
acetoacetyl-CoA (CHEBI:15345) has functional parent acetoacetic acid (CHEBI:15344)
geranyl acetoacetate (CHEBI:85255) has functional parent acetoacetic acid (CHEBI:15344)
acetoacetate (CHEBI:13705) is conjugate base of acetoacetic acid (CHEBI:15344)
acetoacetyl group (CHEBI:48051) is substituent group from acetoacetic acid (CHEBI:15344)
3-hydroxy-3-butenoic acid (CHEBI:131367) is tautomer of acetoacetic acid (CHEBI:15344)
IUPAC Name
3-oxobutanoic acid
Synonyms Sources
3-ketobutanoic acid ChEBI
3-Ketobutyric acid HMDB
3-Oxobutanoic acid KEGG COMPOUND
3-Oxobutyric acid ChemIDplus
Acetoacetic acid KEGG COMPOUND
beta-Ketobutyric acid KEGG COMPOUND
Database Links Databases
3-KETOBUTYRATE MetaCyc
Acetoacetic_acid Wikipedia
C00007458 KNApSAcK
C00164 KEGG COMPOUND
c0069 UM-BBD
DB01762 DrugBank
HMDB00060 HMDB
LMFA01060003 LIPID MAPS
View more database links
Registry Numbers Types Sources
1747690 Beilstein Registry Number Beilstein
1747690 Reaxys Registry Number Reaxys
541-50-4 CAS Registry Number KEGG COMPOUND
541-50-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17190852 PubMed citation Europe PMC
20444635 PubMed citation Europe PMC
21806064 PubMed citation Europe PMC
22382897 PubMed citation Europe PMC
3884391 PubMed citation Europe PMC
Last Modified
06 February 2017