acetoacetic acid (CHEBI:15344)

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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

Supplier Information	eMolecules:537269, ZINC000004543724

Download	Molfile XML SDF

Wikipedia	License
Docosatetraenoic acid designates any straight chain 22:4 fatty acid. (See Essential fatty acid for nomenclature.) One isomer is of particular interest: all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the common name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins, and epoxydocosatrienoic acids (EDTs, also known as dihomo-EETs). In addition to being endothelium-derived hyperpolarizing factors, EDTs have demonstrated anti-endoplasmic reticulum stress and anti-nociceptive activities. They are hydrolyzed by the soluble epoxide hydrolase (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors.
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Formula

C4H6O3

Net Charge

Average Mass

102.08864

Monoisotopic Mass

102.03169

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 )

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) ethyl acetoacetate (CHEBI:4893) 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

Last Modified

05 August 2021