CHEBI:15345 - acetoacetyl-CoA

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ChEBI Name acetoacetyl-CoA
ChEBI ID CHEBI:15345
Definition A 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of acetoacetic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41333, CHEBI:2392, CHEBI:11756, CHEBI:13706, CHEBI:22173
Supplier Information ZINC000008216889
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Oxygen is a chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and a potent oxidizing agent that readily forms oxides with most elements as well as with other compounds. Oxygen is the most abundant element in Earth's crust, and the third-most abundant element in the universe after hydrogen and helium. At standard temperature and pressure, two oxygen atoms will bind covalently to form dioxygen, a colorless and odorless diatomic gas with the chemical formula O2. Dioxygen gas currently constitutes approximately 20.95% molar fraction of the Earth's atmosphere, though this has changed considerably over long periods of time in Earth's history. Oxygen makes up almost half of the Earth's crust in the form of various oxides such as water, carbon dioxide, iron oxides and silicates. All eukaryotic organisms, including plants, animals, fungi, algae and most protists, need oxygen for cellular respiration, which extracts chemical energy by the reaction of oxygen with organic molecules derived from food and releases carbon dioxide as a waste product. In aquatic animals, dissolved oxygen in water is absorbed by specialized respiratory organs called gills, through the skin or via the gut; in terrestrial animals such as tetrapods, oxygen in air is actively taken into the body via specialized organs known as lungs, where gas exchange takes place to diffuse oxygen into the blood and carbon dioxide out, and the body's circulatory system then transports the oxygen to other tissues where cellular respiration takes place. However in insects, the most successful and biodiverse terrestrial clade, oxygen is directly conducted to the internal tissues via a deep network of airways. Many major classes of organic molecules in living organisms contain oxygen atoms, such as proteins, nucleic acids, carbohydrates and fats, as do the major constituent inorganic compounds of animal shells, teeth, and bone. Most of the mass of living organisms is oxygen as a component of water, the major constituent of lifeforms. Oxygen in Earth's atmosphere is produced by biotic photosynthesis, in which photon energy in sunlight is captured by chlorophyll to split water molecules and then react with carbon dioxide to produce carbohydrates and oxygen is released as a byproduct. Oxygen is too chemically reactive to remain a free element in air without being continuously replenished by the photosynthetic activities of autotrophs such as cyanobacteria, chloroplast-bearing algae and plants. A much rarer triatomic allotrope of oxygen, ozone (O3), strongly absorbs the UVB and UVC wavelengths and forms a protective ozone layer at the lower stratosphere, which shields the biosphere from ionizing ultraviolet radiation. However, ozone present at the surface is a corrosive byproduct of smog and thus an air pollutant. Oxygen was isolated by Michael Sendivogius before 1604, but it is commonly believed that the element was discovered independently by Carl Wilhelm Scheele, in Uppsala, in 1773 or earlier, and Joseph Priestley in Wiltshire, in 1774. Priority is often given for Priestley because his work was published first. Priestley, however, called oxygen "dephlogisticated air", and did not recognize it as a chemical element. The name oxygen was coined in 1777 by Antoine Lavoisier, who first recognized oxygen as a chemical element and correctly characterized the role it plays in combustion. Common industrial uses of oxygen include production of steel, plastics and textiles, brazing, welding and cutting of steels and other metals, rocket propellant, oxygen therapy, and life support systems in aircraft, submarines, spaceflight and diving.
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Formula C25H40N7O18P3S
Net Charge 0
Average Mass 851.610
Monoisotopic Mass 851.13634
InChI InChI=1S/C25H40N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1
InChIKey OJFDKHTZOUZBOS-CITAKDKDSA-N
SMILES CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Mus musculus (NCBI:txid10090) From MetaboLights See: MetaboLights Study
Mus musculus (NCBI:txid10090) From MetaboLights See: MetaboLights Study
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Chemical Role(s): acyl donor
Any donor that can transfer acyl groups between molecular entities.
(via acyl-CoA )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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ChEBI Ontology
Outgoing acetoacetyl-CoA (CHEBI:15345) has functional parent acetoacetic acid (CHEBI:15344)
acetoacetyl-CoA (CHEBI:15345) has functional parent butyryl-CoA (CHEBI:15517)
acetoacetyl-CoA (CHEBI:15345) has role Escherichia coli metabolite (CHEBI:76971)
acetoacetyl-CoA (CHEBI:15345) has role mouse metabolite (CHEBI:75771)
acetoacetyl-CoA (CHEBI:15345) is a 3-oxo-fatty acyl-CoA (CHEBI:15489)
acetoacetyl-CoA (CHEBI:15345) is conjugate acid of acetoacetyl-CoA(4−) (CHEBI:57286)
Incoming acetoacetyl-CoA(4−) (CHEBI:57286) is conjugate base of acetoacetyl-CoA (CHEBI:15345)
IUPAC Name
3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxobutanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate}
Synonyms Sources
3-Acetoacetyl-CoA KEGG COMPOUND
acetoacetyl CoA KNApSAcK
Acetoacetyl coenzyme A KEGG COMPOUND
Acetoacetyl-CoA KEGG COMPOUND
S-acetoacetyl-CoA ChEBI
S-Acetoacetyl-coenzym A ChEBI
S-acetoacetyl-coenzyme A ChEBI
Manual Xrefs Databases
Acetoacetyl-CoA Wikipedia
C00007269 KNApSAcK
C00332 KEGG COMPOUND
c0229 UM-BBD
CAA PDBeChem
DB03059 DrugBank
FDB022648 FooDB
HMDB0001484 HMDB
LMFA07050030 LIPID MAPS
View more database links
Registry Numbers Types Sources
1420-36-6 CAS Registry Number KEGG COMPOUND
1420-36-6 CAS Registry Number ChemIDplus
78273 Reaxys Registry Number Reaxys
Citations Types Sources
10806397 PubMed citation Europe PMC
11137815 PubMed citation Europe PMC
11451959 PubMed citation Europe PMC
12501183 PubMed citation Europe PMC
1682408 PubMed citation Europe PMC
16887802 PubMed citation Europe PMC
239468 PubMed citation Europe PMC
24211201 PubMed citation Europe PMC
26527136 PubMed citation Europe PMC
27093562 PubMed citation Europe PMC
27124816 PubMed citation Europe PMC
28062645 PubMed citation Europe PMC
29226071 PubMed citation Europe PMC
32218776 PubMed citation Europe PMC
6118268 PubMed citation Europe PMC
6150478 PubMed citation Europe PMC
7857927 PubMed citation Europe PMC
Last Modified
08 June 2021