Acetoacetyl-CoA

Acetoacetyl-CoA
Names
	Preferred IUPAC name S-{(9R)-1-[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-3,5,10,14-tetraoxo-2,4,6-trioxa-11,15-diaza-3λ5,5λ5-diphosphaheptadecan-17-yl} 3-oxobutanethioate
Identifiers
CAS Number	1420-36-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15345 ;
ChemSpider	83198 ;
ECHA InfoCard	100.014.378
IUPHAR/BPS	3039;
MeSH	acetoacetyl+CoA
PubChem CID	74;
CompTox Dashboard (EPA)	DTXSID30931292 ;
	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 Key: OJFDKHTZOUZBOS-CITAKDKDSA-N ; InChI=1/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 Key: OJFDKHTZOUZBOS-CITAKDKDBD;
	SMILES O=C(C)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O;
Properties
Chemical formula	C25H40N7O18P3S
Molar mass	851.609 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	Infobox references

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,^[1] 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.^[2] This deficiency is classified as a disorder ketone body and isoleucine metabolism that can be inherited.^[3]

References[]

^ Yurkanis, Bruice, Paula (2017). Organic chemistry. Pearson. ISBN 9780134042282. OCLC 974910578.
^ Tsuda, Hirohisa; Shiraki, Mari; Inoue, Eri; Saito, Terumi (August 2016). "Generation of poly-β-hydroxybutyrate from acetate in higher plants: Detection of acetoacetyl CoA reductase- and PHB synthase- activities in rice". Journal of Plant Physiology. 201: 9–16. doi:10.1016/j.jplph.2016.06.007. ISSN 0176-1617. PMID 27372278.
^ Bose, K. S.; Sarma, R. H. (1975-10-27). "Delineation of the intimate details of the backbone conformation of pyridine nucleotide coenzymes in aqueous solution". Biochemical and Biophysical Research Communications. 66 (4): 1173–1179. doi:10.1016/0006-291x(75)90482-9. ISSN 1090-2104. PMID 2.