Page last updated: 2024-12-04

acetoacetic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

acetoacetic acid : A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID96
CHEMBL ID1230762
CHEBI ID15344
SCHEMBL ID13341499
SCHEMBL ID6620
MeSH IDM0066777

Synonyms (40)

Synonym
CHEMBL1230762
4387-93-3
butanoic acid, 3-oxo-
acetylacetic acid
acetonecarboxylic acid
3-oxobutyric acid
3-KETOBUTYRATE ,
acetoacetic acid
541-50-4
C00164
beta-ketobutyric acid
3-oxobutanoic acid
3-oxo-butyric acid
CHEBI:15344 ,
3-ketobutanoic acid
3-ketobutyric acid
DB01762
LMFA01060003
3-oxo-butanoic acid
AAE ,
A6DBA337-E696-4022-A9F9-1757E3CDBFAE
AKOS006241271
4zi204y1mc ,
unii-4zi204y1mc
.alpha.-ketobutyrate
acetoacetic acid [mi]
WDJHALXBUFZDSR-UHFFFAOYSA-N
SCHEMBL13341499
SCHEMBL6620
3-oxobutanoicacid
AM85395
DTXSID00202441 ,
quadrapure(r) ak, 50-90 mesh, extent of labeling: 2.0-3.0 mmol/g loading, 1 % cross-linked with divinylbenzene
3-oxobutyrate
Q409692
lithium-acetoacetate
EN300-106488
HY-112540
CS-0046333
dtxcid00124932

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" It was determined that ketone bodies such as beta-hydroxybutyrate and acetoacetate were important in separating the toxic from the nontoxic phenotypes."( Using dynamic gene module map analysis to identify targets that modulate free fatty acid induced cytotoxicity.
Chan, C; Findlan, R; Li, Z; Srivastava, S,
)
0.13

Pharmacokinetics

ExcerptReferenceRelevance
" Under the graphically measured half-life of 17 minutes for the MCT/LCT emulsion, rapid and complete elimination could be seen after the infusion had been stopped."( [Pharmacokinetic studies of a new 20% fat emulsion containing 70% medium-chain triglycerides].
Kleine, R; Lessire, H; Mertes, N; Pfisterer, M; Puchstein, C; Winde, G; Zander, J, 1990
)
0.28
" Furthermore, the plasma oxipurinol half-life was increased from 27."( Sustained reductions in oxipurinol renal clearance during a restricted diet.
Berlinger, WG; Kitt, TM; Park, GD; Spector, R; Tsalikian, E, 1987
)
0.27

Compound-Compound Interactions

ExcerptReferenceRelevance
" When acetoacetate, beta-hydroxybutyrate, or KIC were combined with MMS, or either ketone body was combined with lactate, insulin release was stimulated 10-fold to 20-fold the controls (almost as much as with glucose)."( Acetoacetate and beta-hydroxybutyrate in combination with other metabolites release insulin from INS-1 cells and provide clues about pathways in insulin secretion.
Brown, LJ; Hasan, NM; Kendrick, MA; Longacre, MJ; MacDonald, MJ; Stoker, SW, 2008
)
0.35

Dosage Studied

ExcerptRelevanceReference
" It is concluded that high dosed caffeine causes peripheral insulin resistance in the human being as well as in the experimental animal."( [Effect of caffeine on various metabolic parameters in vivo].
Förster, H; Sachs, M, 1984
)
0.27
"A method for sampling, for preservation of these samples and for dosage has been studied in order to gain a better knowledge of the usual values and the physiological and pathological variations of beta-hydroxybutyrate and of acetoacetate in the blood and milk of cattle."( [Technical study of hydroxybutyrate and acetoacetate levels in blood and milk of cattle].
André, F; Coppin, F, 1982
)
0.26
" A lignolytic enzyme preparation produced by the thermophilic fungus Thermomyces lanuginosus was applied in the present experiment and fed to dairy cows at 34 g/day dosage in the period between calving and the 110th day of lactation."( Effects of a non-starch polysaccharidase enzyme preparation from Thermomyces lanuginosus on energy and protein metabolism and milk yield of dairy cattle.
Bartyik, J; Bata, A; Brydl, E; Fülöp, A; Jurkovich, V; Könyves, L; Kutasi, J; Nagy, G; Rafai, P; Tegzes, L, 2002
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
ketone bodyA carbonyl compound produced as a water-soluble byproduct when fatty acids are broken down for energy in the liver. There are three endogenous ketone bodies: acetone, acetoacetic acid, and (R)-3-hydroxybutyric acid; others may be produced as a result of the metabolism of synthetic triglycerides.
3-oxo fatty acidAny oxo fatty acid in which an oxo substituent is located at position 3.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (52)

PathwayProteinsCompounds
Metabolism14961108
Metabolism of lipids500463
Ketone body metabolism1019
Synthesis of Ketone Bodies817
Ketone body catabolism410
Ketone Body Metabolism413
Valine, Leucine, and Isoleucine Degradation2852
Tyrosine Metabolism1657
Butyrate Metabolism718
Phenylalanine and Tyrosine Metabolism1121
beta-Ketothiolase Deficiency2852
2-Methyl-3-hydroxybutyryl-CoA Dehydrogenase Deficiency2852
Propionic Acidemia2852
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency2852
Maple Syrup Urine Disease2852
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I2852
3-Methylglutaconic Aciduria Type I2852
3-Methylglutaconic Aciduria Type III2852
Methylmalonate Semialdehyde Dehydrogenase Deficiency2852
Methylmalonic Aciduria2852
Isovaleric Aciduria2852
Phenylketonuria1121
Tyrosinemia Type 2 (or Richner-Hanhart Syndrome)1121
Tyrosinemia Type 3 (TYRO3)1121
Fatty Acid Biosynthesis233
Alkaptonuria1657
Hawkinsinuria1657
Tyrosinemia Type I1657
3-Methylglutaconic Aciduria Type IV2852
Disulfiram Action Pathway2366
Tyrosinemia, Transient, of the Newborn1657
Dopamine beta-Hydroxylase Deficiency1657
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency2852
3-Hydroxyisobutyric Aciduria2852
Isobutyryl-CoA Dehydrogenase Deficiency2852
Isovaleric Acidemia2852
Monoamine Oxidase-A Deficiency (MAO-A)1657
Succinyl CoA: 3-Ketoacid CoA Transferase Deficiency413
Acetate Metabolism611
Butanoate Metabolism922
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency2952
Butanoate metabolism ( Butanoate metabolism )1518
Succinyl-CoA + Acetoacetic acid = Succinic acid + Acetoacetyl-CoA ( Valine,Leucine and Isoleucine degradation )14
NAD+ + (R)-3-Hydroxy-butanoic acid = NADH + Acetoacetic acid ( Butanoate metabolism )14
(S)-3-Hydroxy-3-methyl-glutaryl-CoA = Acetyl-CoA + Acetoacetic acid ( Valine,Leucine and Isoleucine degradation )13
Tyrosine metabolism ( Tyrosine metabolism )2841
Valine,Leucine and Isoleucine degradation ( Valine,Leucine and Isoleucine degradation )2936
Ketogenesis and ketolysis89
Synthesis and degradation of ketone bodies01
Valine, leucine and isoleucine degradation034
Metabolism overview078
Biochemical pathways: part I0466
tyrosine degradation I212

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
lactate transmembrane transportMonocarboxylate transporter 4Homo sapiens (human)
pyruvate catabolic processMonocarboxylate transporter 4Homo sapiens (human)
pyruvate transmembrane transportMonocarboxylate transporter 4Homo sapiens (human)
monocarboxylic acid transportMonocarboxylate transporter 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
RNA bindingMonocarboxylate transporter 4Homo sapiens (human)
protein bindingMonocarboxylate transporter 4Homo sapiens (human)
monocarboxylic acid transmembrane transporter activityMonocarboxylate transporter 4Homo sapiens (human)
lactate:proton symporter activityMonocarboxylate transporter 4Homo sapiens (human)
pyruvate transmembrane transporter activityMonocarboxylate transporter 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
membraneMonocarboxylate transporter 4Homo sapiens (human)
basolateral plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
apical plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
lateral plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
nuclear membraneMonocarboxylate transporter 4Homo sapiens (human)
plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
basolateral plasma membraneMonocarboxylate transporter 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID681140TP_TRANSPORTER: uptake in Xenopus laevis oocytes2000The Journal of physiology, Dec-01, Volume: 529 Pt 2Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle.
AID681123TP_TRANSPORTER: inhibition of lactate uptake in Xenopus laevis oocytes1999The Biochemical journal, Aug-01, Volume: 341 ( Pt 3)Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes.
AID679844TP_TRANSPORTER: inhibition of lactate uptake (Lactate:0.1mM, Acetoacetate:50mM, preincubation with aminoxyacetate) in Xenopus laevis oocytes1997The Journal of biological chemistry, Nov-28, Volume: 272, Issue:48
Comparison of lactate transport in astroglial cells and monocarboxylate transporter 1 (MCT 1) expressing Xenopus laevis oocytes. Expression of two different monocarboxylate transporters in astroglial cells and neurons.
AID681605TP_TRANSPORTER: change in intracellular pH(pHi)value in Xenopus laevis oocytes1998The Biochemical journal, Jul-01, Volume: 333 ( Pt 1)Characterization of the monocarboxylate transporter 1 expressed in Xenopus laevis oocytes by changes in cytosolic pH.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (974)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990494 (50.72)18.7374
1990's206 (21.15)18.2507
2000's130 (13.35)29.6817
2010's108 (11.09)24.3611
2020's36 (3.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 78.07

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index78.07 (24.57)
Research Supply Index6.95 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index139.62 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (78.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials29 (2.87%)5.53%
Reviews28 (2.77%)6.00%
Case Studies17 (1.68%)4.05%
Observational1 (0.10%)0.25%
Other935 (92.57%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]