1.0 2011-04-11 15:41:11 UTC 2019-11-26 03:20:53 UTC FDB021801 3-Oxobutanoic acid, 9CI It 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] 3-Ketobutanoate 3-Ketobutanoic acid 3-Ketobutyrate 3-Ketobutyric acid 3-Oxobutyrate 3-Oxobutyric acid Acetoacetate Acetoacetic acid Acetonecarboxylic acid Acetylacetic acid b-Ketobutyrate b-Ketobutyric acid beta-Ketobutyrate beta-Ketobutyric acid Diacetate Diacetic acid β-ketobutyrate β-ketobutyric acid C8H12O6 204.1773 204.063388116 (2E)-3-hydroxybut-2-enoic acid; 3-oxobutanoic acid (2E)-3-hydroxybut-2-enoic acid; acetoacetic acid 541-50-4 CC(=O)CC(O)=O.C\C(O)=C/C(O)=O InChI=1S/2C4H6O3/c2*1-3(5)2-4(6)7/h2H2,1H3,(H,6,7);2,5H,1H3,(H,6,7)/b;3-2+ UNNIHLXYGZEWRE-ZPYUXNTASA-N 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. Short-chain keto acids and derivatives Organic compounds Organic acids and derivatives Keto acids and derivatives Short-chain keto acids and derivatives 1,3-dicarbonyl compounds Beta-hydroxy ketones Beta-keto acids and derivatives Carboxylic acids Enols Hydrocarbon derivatives Hydroxy fatty acids Monocarboxylic acids and derivatives Organic oxides Unsaturated fatty acids Vinylogous acids 1,3-dicarbonyl compound Aliphatic acyclic compound Beta-hydroxy ketone Beta-keto acid Carbonyl group Carboxylic acid Carboxylic acid derivative Enol Fatty acid Fatty acyl Hydrocarbon derivative Hydroxy fatty acid Ketone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Short-chain keto acid Unsaturated fatty acid Vinylogous acid Solid logp -0.20 ALOGPS logs 0.09 ALOGPS solubility 1.25e+02 g/l ALOGPS logp 0.015 ChemAxon pka_strongest_acidic 4.34 ChemAxon pka_strongest_basic -6.1 ChemAxon iupac (2E)-3-hydroxybut-2-enoic acid; 3-oxobutanoic acid ChemAxon average_mass 204.1773 ChemAxon mono_mass 204.063388116 ChemAxon smiles CC(=O)CC(O)=O.C\C(O)=C/C(O)=O ChemAxon formula C8H12O6 ChemAxon inchi InChI=1S/2C4H6O3/c2*1-3(5)2-4(6)7/h2H2,1H3,(H,6,7);2,5H,1H3,(H,6,7)/b;3-2+ ChemAxon inchikey UNNIHLXYGZEWRE-ZPYUXNTASA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 25.09 ChemAxon polarizability 9.11 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Butyrate Metabolism SMP00073 map00650 Fatty Acid Biosynthesis SMP00456 Ketone Body Metabolism SMP00071 map00072 Phenylalanine and Tyrosine Metabolism SMP00008 map00360 Tyrosine Metabolism SMP00006 map00350 Valine, Leucine and Isoleucine Degradation SMP00032 map00280 HMDB00060 AAE #<Reference:0x000055ce3252c460> #<Reference:0x000055ce3252c2a8> #<Reference:0x000055ce3252c0f0> #<Reference:0x000055ce3252bee8> #<Reference:0x000055ce3252bd30> #<Reference:0x000055ce3252bb78> #<Reference:0x000055ce3252b9c0> #<Reference:0x000055ce3252b808> #<Reference:0x000055ce3252b650> #<Reference:0x000055ce3252b498> #<Reference:0x000055ce3252b2e0> #<Reference:0x000055ce3252b128> #<Reference:0x000055ce3252af20> #<Reference:0x000055ce3252acf0> #<Reference:0x000055ce3252ab10> #<Reference:0x000055ce3252a958> #<Reference:0x000055ce3252a7a0> #<Reference:0x000055ce3252a5e8> #<Reference:0x000055ce3252a430> #<Reference:0x000055ce3252a250> #<Reference:0x000055ce3252a070> Beer Type 2 specific 0.0205 0.023 0.018 mg/100 g Milk (Cow) Type 2 specific 23.5 40.0 7.0 uM 3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic Q8TB92 HMGCLL1 Acetoacetyl-CoA synthetase Q86V21 AACS Hydroxymethylglutaryl-CoA lyase, mitochondrial P35914 HMGCL Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrial P55809 OXCT1 Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrial Q9BYC2 OXCT2