1.02011-04-11 15:41:11 UTC2019-11-26 03:20:53 UTCFDB0218013-Oxobutanoic acid, 9CIIt 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-Ketobutanoate3-Ketobutanoic acid3-Ketobutyrate3-Ketobutyric acid3-Oxobutyrate3-Oxobutyric acidAcetoacetateAcetoacetic acidAcetonecarboxylic acidAcetylacetic acidb-Ketobutyrateb-Ketobutyric acidbeta-Ketobutyratebeta-Ketobutyric acidDiacetateDiacetic acidβ-ketobutyrateβ-ketobutyric acidC8H12O6204.1773204.063388116(2E)-3-hydroxybut-2-enoic acid; 3-oxobutanoic acid(2E)-3-hydroxybut-2-enoic acid; acetoacetic acid541-50-4CC(=O)CC(O)=O.C\C(O)=C/C(O)=OInChI=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 derivativesOrganic compoundsOrganic acids and derivativesKeto acids and derivativesShort-chain keto acids and derivatives1,3-dicarbonyl compoundsBeta-hydroxy ketonesBeta-keto acids and derivativesCarboxylic acidsEnolsHydrocarbon derivativesHydroxy fatty acidsMonocarboxylic acids and derivativesOrganic oxidesUnsaturated fatty acidsVinylogous acids1,3-dicarbonyl compoundAliphatic acyclic compoundBeta-hydroxy ketoneBeta-keto acidCarbonyl groupCarboxylic acidCarboxylic acid derivativeEnolFatty acidFatty acylHydrocarbon derivativeHydroxy fatty acidKetoneMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundShort-chain keto acidUnsaturated fatty acidVinylogous acidSolidlogp-0.20logs0.09solubility1.25e+02 g/llogp0.015pka_strongest_acidic4.34pka_strongest_basic-6.1iupac(2E)-3-hydroxybut-2-enoic acid; 3-oxobutanoic acidaverage_mass204.1773mono_mass204.063388116smilesCC(=O)CC(O)=O.C\C(O)=C/C(O)=OformulaC8H12O6inchiInChI=1S/2C4H6O3/c2*1-3(5)2-4(6)7/h2H2,1H3,(H,6,7);2,5H,1H3,(H,6,7)/b;3-2+inchikeyUNNIHLXYGZEWRE-ZPYUXNTASA-Npolar_surface_area57.53refractivity25.09polarizability9.11rotatable_bond_count3acceptor_count3donor_count2physiological_charge-1formal_charge0Butyrate MetabolismSMP00073map00650Fatty Acid BiosynthesisSMP00456Ketone Body MetabolismSMP00071map00072Phenylalanine and Tyrosine MetabolismSMP00008map00360Tyrosine MetabolismSMP00006map00350Valine, Leucine and Isoleucine DegradationSMP00032map00280HMDB00060AAE#<Reference:0x0000555675e243b8>#<Reference:0x0000555675e24200>#<Reference:0x0000555675e24048>#<Reference:0x0000555675e23d50>#<Reference:0x0000555675e23aa8>#<Reference:0x0000555675e23800>#<Reference:0x0000555675e23558>#<Reference:0x0000555675e232b0>#<Reference:0x0000555675e230f8>#<Reference:0x0000555675e22f40>#<Reference:0x0000555675e22d60>#<Reference:0x0000555675e22ba8>#<Reference:0x0000555675e229f0>#<Reference:0x0000555675e22838>#<Reference:0x0000555675e22680>#<Reference:0x0000555675e224a0>#<Reference:0x0000555675e222e8>#<Reference:0x0000555675e22130>#<Reference:0x0000555675e21f50>#<Reference:0x0000555675e21d48>#<Reference:0x0000555675e21b68>BeerType 2specific0.02050.0230.018mg/100 gMilk (Cow)Type 2specific23.540.07.0uM3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmicQ8TB92HMGCLL1Acetoacetyl-CoA synthetaseQ86V21AACSHydroxymethylglutaryl-CoA lyase, mitochondrialP35914HMGCLSuccinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrialP55809OXCT1Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrialQ9BYC2OXCT2