Acetoacetyl-CoA

Acetoacetyl-CoA
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).
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	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.

Mevalonate pathway

References

Yurkanis, Bruice, Paula (2017). Organic chemistry. Pearson. ISBN 9780134042282. OCLC 974910578.

Acetoacetyl-CoA

References

See also