Record Information
Version1.0
Creation date2011-04-11 15:41:11 UTC
Update date2019-11-26 03:20:53 UTC
Primary IDFDB021801
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Oxobutanoic acid, 9CI
DescriptionIt is a weak organic acid and can be produced in the human liver under certain conditions of poor metabolism leading to excessive fatty acid breakdown (diabetes mellitus leading to diabetic ketoacidosis), it is then partially converted to acetone by decarboxylation and excreted either in urine or through respiration. Persistent mild hyperketonemia is a common finding in newborns. These compounds serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing rats. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 wk of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies are utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life. (PMID 3884391) The acid is also present in the metabolism of those undergoing starvation or prolonged physical exertion as part of gluconeogenesis. When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid or acetone, is what is detected. [HMDB]
CAS Number541-50-4
Structure
Thumb
Synonyms
SynonymSource
3-Oxobutanoate, 9ciGenerator
3-KetobutanoateGenerator
3-Ketobutanoic acidChEBI
3-KetobutyrateGenerator
3-Ketobutyric acidChEBI
3-OxobutyrateGenerator
3-Oxobutyric acidChEBI
AcetoacetateGenerator
Acetoacetic aciddb_source
Acetonecarboxylic aciddb_source
Acetylacetic aciddb_source
b-KetobutyrateGenerator
b-Ketobutyric acidGenerator
beta-KetobutyrateGenerator
beta-Ketobutyric acidChEBI
DiacetateHMDB
Diacetic aciddb_source
β-ketobutyrateGenerator
β-ketobutyric acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility125 g/LALOGPS
logP-0.2ALOGPS
logP0.015ChemAxon
logS0.09ALOGPS
pKa (Strongest Acidic)4.34ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.09 m³·mol⁻¹ChemAxon
Polarizability9.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H12O6
IUPAC name(2E)-3-hydroxybut-2-enoic acid; 3-oxobutanoic acid
InChI IdentifierInChI=1S/2C4H6O3/c2*1-3(5)2-4(6)7/h2H2,1H3,(H,6,7);2,5H,1H3,(H,6,7)/b;3-2+
InChI KeyUNNIHLXYGZEWRE-ZPYUXNTASA-N
Isomeric SMILESCC(=O)CC(O)=O.C\C(O)=C/C(O)=O
Average Molecular Weight204.1773
Monoisotopic Molecular Weight204.063388116
Classification
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
  • Hydroxy fatty acid
  • Beta-keto acid
  • Fatty acyl
  • Fatty acid
  • 1,3-dicarbonyl compound
  • Unsaturated fatty acid
  • Beta-hydroxy ketone
  • Vinylogous acid
  • Ketone
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID94
ChEMBL IDNot Available
KEGG Compound IDC00164
Pubchem Compound ID96
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01762
HMDB IDHMDB00060
CRC / DFC (Dictionary of Food Compounds) IDDFR99-E:DFR99-E
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1485291
KNApSAcK IDNot Available
HET IDAAE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Hydroxymethylglutaryl-CoA lyase, mitochondrialHMGCLP35914
Acetoacetyl-CoA synthetaseAACSQ86V21
Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrialOXCT1P55809
Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrialOXCT2Q9BYC2
3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmicHMGCLL1Q8TB92
Pathways
NameSMPDB LinkKEGG Link
Butyrate MetabolismSMP00073 map00650
Fatty Acid BiosynthesisSMP00456 Not Available
Ketone Body MetabolismSMP00071 map00072
Phenylalanine and Tyrosine MetabolismSMP00008 map00360
Tyrosine MetabolismSMP00006 map00350
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference