Structure via PubChem · Public domain (PubChem)
acetoacetyl-CoA
Sign in to saveAlso known as 3-acetoacetyl-CoA, acetoacetyl coenzyme A, acetoacetyl-coenzyme a, S-acetoacetyl-coenzyme A, S-acetoacetyl-CoA, 3-Acetoacetyl-CoA, S-Acetoacetyl-coenzym A, Acetoacetyl-Coenzyme A
Acetoacetyl CoA is the precursor of HMG-CoA in the mevalonate pathway, which is essential for cholesterol biosynthesis. It also takes a similar role in the ketone bodies synthesis (ketogenesis) pathway of the liver. In the ketone bodies digestion pathway (in the tissue), it is no longer associated with having HMG-CoA as a product or as a reactant.
Chemical data
- Formula
- C25H40N7O18P3S
- Molecular weight
- 851.6 g/mol
- IUPAC name
- S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 3-oxobutanethioate
- SMILES
- CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O
- InChIKey
- OJFDKHTZOUZBOS-CITAKDKDSA-N
- XLogP
- -5.8
- Polar surface area
- 406 Ų
- H-bond donors
- 9
- H-bond acceptors
- 23
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 851.136
Show 5 more facts
- chemical formula
- C₂₅H₄₀N₇O₁₈P₃S
- canonical SMILES
- CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)OP(=O)(O)O)O
- isomeric SMILES
- CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C2N=CN=C3N)O)OP(=O)(O)O)O
- found in taxon
- Caenorhabditis elegans
- subject has role
- primary metabolite
via Wikidata · CC0
~4 min read
Encyclopedic overview
4 sectionsContents
- Mutations
- Additional application
- See also
- References
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477239005 | ImageFile=Acetoacetyl coenzyme A.svg | ImageSize=300px | IUPACName=3′-O-Phosphonoadenosine 5′-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxobutanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl dihydrogen diphosphate] | SystematicName=O1-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxobutanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate | OtherNames= |Section1= |Section2= |Section3= }} Acetoacetyl CoA is the precursor of HMG-CoA in the mevalonate pathway, which is essential for cholesterol biosynthesis. It also takes a similar role in the ketone bodies synthesis (ketogenesis) pathway of the liver. In the ketone bodies digestion pathway (in the tissue), it is no longer associated with having HMG-CoA as a product or as a reactant.
It is created from acetyl-CoA, a thioester, which reacts with the enolate of a second molecule of acetyl-CoA in a Claisen condensation reaction, and it is acted upon by HMG-CoA synthase to form HMG-CoA. During the metabolism of leucine, this last reaction is reversed. Some individuals may experience Acetoacetyl-CoA deficiency. This deficiency is classified as a disorder ketone body and isoleucine metabolism that can be inherited. Additional mutations include those with the enzymes within pathways related to Acetoacetyl CoA, including Beta-Ketothiolase deficiency and Mitochondrial 3-hydroxy-3-methylglutaryl-CoA Synthase mutation.
Excerpted from Wikipedia’s “acetoacetyl-CoA” article, available under the CC BY-SA 4.0 licence.