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Record Information
Version1.0
Creation Date2016-09-30 22:19:07 UTC
Update Date2020-05-21 16:28:30 UTC
BMDB IDBMDB0000060
Secondary Accession Numbers
  • BMDB00060
Metabolite Identification
Common NameAcetoacetic acid
DescriptionAcetoacetic acid, also known as 3-oxobutyrate or 3-oxobutanoic acid, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Acetoacetic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Acetoacetic acid exists in all living species, ranging from bacteria to humans. Acetoacetic acid is a potentially toxic compound. Acetoacetic acid has been found to be associated with several diseases known as ketoacidosis, irritable bowel syndrome, anoxia, and diabetes mellitus type 2; also acetoacetic acid has been linked to the inborn metabolic disorders including glucose transporter type 1 deficiency syndrome.
Structure
Thumb
Synonyms
ValueSource
3-Ketobutanoic acidChEBI
3-Ketobutyric acidChEBI
3-Oxobutanoic acidChEBI
3-Oxobutyric acidChEBI
beta-Ketobutyric acidChEBI
3-KetobutanoateGenerator
3-KetobutyrateGenerator
3-OxobutanoateGenerator
3-OxobutyrateGenerator
b-KetobutyrateGenerator
b-Ketobutyric acidGenerator
beta-KetobutyrateGenerator
Β-ketobutyrateGenerator
Β-ketobutyric acidGenerator
AcetoacetateGenerator
3-oxo-ButanoateHMDB
3-oxo-Butanoic acidHMDB
DiacetateHMDB
Diacetic acidHMDB
Acetoacetic acid, sodium saltHMDB
Acetoacetic acid, calcium saltHMDB
Acetoacetic acid, lithium saltHMDB
OxobutyrateHMDB
Sodium acetoacetateHMDB
Chemical FormulaC4H6O3
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
IUPAC Name3-oxobutanoic acid
Traditional Nameacetoacetic acid
CAS Registry Number541-50-4
SMILES
CC(=O)CC(O)=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
InChI KeyWDJHALXBUFZDSR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Beta-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point36.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.47ALOGPS
logP-0.0015ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.54 m³·mol⁻¹ChemAxon
Polarizability9.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kk-3940000000-008eb78d2ba3cfa053b4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9500000000-c3940e591f8aef9d6aacView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9800000000-67a95675672c3f5447a7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4950000000-1778836b3908a79b814fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4950000000-4039bb48c98ec17b5c0cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kk-3940000000-008eb78d2ba3cfa053b4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9500000000-c3940e591f8aef9d6aacView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9800000000-67a95675672c3f5447a7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-4950000000-1778836b3908a79b814fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-4950000000-4039bb48c98ec17b5c0cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-9f6c0d100736f4d183c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0100-9600000000-470bf0676151478bca3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-9200000000-9b4ab7b6a41632cb125bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0udi-6900000000-cfab9d4cdb56acafe8ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pb9-9800000000-108aa5ef93455fb1ba28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9100000000-869e2338bbadb32272d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9400000000-081c4a1a05f5581a5ffbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9100000000-960a06fd90db43d3e0f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-bd091454ccc8f532b42eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-9700000000-b01f47bb6cd4f1043983View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-d2649829e8a79045e73bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1486ce68d51ba83ed499View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Blood
  • Fibroblasts
  • Leukocyte
  • Liver
  • Milk
  • Neuron
  • Ruminal Fluid
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Trabi M, Keller M...
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FibroblastsExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LeukocyteExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified4 - 14 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified40 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SpleenExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Treated with growth-promoting hormones
details
HMDB IDHMDB0000060
DrugBank IDDB01762
Phenol Explorer Compound IDNot Available
FooDB IDFDB021801
KNApSAcK IDC00007458
Chemspider ID94
KEGG Compound IDC00164
BioCyc ID3-KETOBUTYRATE
BiGG ID1485291
Wikipedia LinkAcetoacetic_acid
METLIN ID276
PubChem Compound96
PDB IDNot Available
ChEBI ID15344
References
Synthesis ReferenceLopez-Soriano, F. J.; Argiles, J. M. A simple method for the preparation of acetoacetate. Analytical Letters (1985), 18(B5), 589-92.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0. [PubMed:11286410 ]
  2. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  3. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  4. Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities as an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
Q71SP7
Molecular weight:
274554.0
Reactions
Malonic acid + Acetic acid → Acetoacetic aciddetails
Acetoacetic acid → 3-Hydroxybutyric aciddetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
FAH
Uniprot ID:
A5PKH3
Molecular weight:
46156.0
Reactions
4-Fumarylacetoacetic acid + Water → Acetoacetic acid + Fumaric aciddetails
General function:
Energy production and conversion
Specific function:
Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2-hydroxyglutarate (D-2-HG). L-3-hydroxybutyrate (L-3-OHB) is also a substrate for HOT when using 2-KG as hydrogen acceptor, resulting in the formation of D-2-HG (By similarity).
Gene Name:
ADHFE1
Uniprot ID:
A6QP15
Molecular weight:
50343.0
General function:
Lipid transport and metabolism
Specific function:
Dehydrogenase that mediates the formation of 2,5-dihydroxybenzoic acid (2,5-DHBA), a siderophore that shares structural similarities with bacterial enterobactin and associates with LCN2, thereby playing a key role in iron assimilation and homeostasis. Plays a role in susceptibility to bacterial infection by providing an assimilable source of iron that is exploited by pathogenic bacteria (By similarity). Also acts as a 3-hydroxybutyrate dehydrogenase (By similarity).
Gene Name:
BDH2
Uniprot ID:
Q3T046
Molecular weight:
26662.0
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
BDH1
Uniprot ID:
Q02337
Molecular weight:
38391.0
Reactions
(R)-3-Hydroxybutyric acid + NAD → Acetoacetic acid + NADHdetails
General function:
Amino acid transport and metabolism
Specific function:
Mitochondrial 3-hydroxymethyl-3-methylglutaryl-CoA lyase that catalyzes a cation-dependent cleavage of (S)-3-hydroxy-3-methylglutaryl-CoA into acetyl-CoA and acetoacetate, a key step in ketogenesis. Terminal step in leucine catabolism. Ketone bodies (beta-hydroxybutyrate, acetoacetate and acetone) are essential as an alternative source of energy to glucose, as lipid precursors and as regulators of metabolism.
Gene Name:
HMGCL
Uniprot ID:
Q29448
Molecular weight:
34168.0
Reactions
3-Hydroxy-3-methylglutaryl-CoA → Acetoacetic acid + Acetyl-CoAdetails
3-Hydroxy-3-methylglutaryl-CoA → Acetoacetic aciddetails
General function:
Not Available
Specific function:
Key enzyme for ketone body catabolism. Transfers the CoA moiety from succinate to acetoacetate. Formation of the enzyme-CoA intermediate proceeds via an unstable anhydride species formed between the carboxylate groups of the enzyme and substrate.
Gene Name:
OXCT1
Uniprot ID:
Q24JZ7
Molecular weight:
56453.0
Reactions
Acetoacetic acid + Succinyl-CoA → Succinic acid + Acetoacetyl-CoAdetails
Acetoacetic acid + Succinyl-CoA → Acetoacetyl-CoA + Succinic aciddetails