Stearoyl-CoA

Stearoyl-CoA
Names
	IUPAC name 3′-O-Phosphonoadenosine 5′-{(3R)-3-hydroxy-2,2-dimethyl-4-[(3-{[2-(octadecanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-4-oxobutyl dihydrogen diphosphate}
	Systematic IUPAC name 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-[(3-{[2-(octadecanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-4-oxobutyl} dihydrogen diphosphate
	Other names S-Stearoylcoenzyme A, Stearyl-CoA, Octadecanoyl-coenzyme A, Octadecanoyl-CoA, stearyl coenzyme A
Identifiers
CAS Number	362-66-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15541;
ChemSpider	84957;
ECHA InfoCard	100.006.045
KEGG	C00412;
PubChem CID	94140;
UNII	OBC49BV194 ;
CompTox Dashboard (EPA)	DTXSID80863110 ;
	InChI InChI=1S/C39H70N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h26-28,32-34,38,49-50H,4-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/t28-,32-,33-,34+,38-/m1/s1 Key: SIARJEKBADXQJG-LFZQUHGESA-N;
	SMILES CCCCCCCCCCCCCCCCCC(=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;
Properties
Chemical formula	C39H70N7O17P3S
Molar mass	1034.00 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Stearoyl-CoA is a coenzyme involved in the metabolism of fatty acids.^[1] Stearoyl-CoA is an 18-carbon long fatty acyl-CoA chain that participates in an unsaturation reaction. The reaction is catalyzed by the enzyme stearoyl-CoA desaturase, which is located in the endoplasmic reticulum.^[2] It forms a cis-double bond between the ninth and tenth carbons within the chain to form the product oleoyl-CoA.^[3]

References

^ Ntambi, J. M. (2002). "Loss of stearoyl-CoA desaturase-1 function protects mice against adiposity". Proceedings of the National Academy of Sciences. 99 (17): 11482–11486. Bibcode:2002PNAS...9911482N. doi:10.1073/pnas.132384699. ISSN 0027-8424. PMC 123282. PMID 12177411.
^ Ntambi, James (2013). Stearoyl-CoA Desaturase Genes in Lipid Metabolism. Springer. ISBN 978-1-4614-7969-7.
^ Igal, R. Ariel (December 2016). "Stearoyl CoA desaturase-1: New insights into a central regulator of cancer metabolism". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1861 (12): 1865–1880. doi:10.1016/j.bbalip.2016.09.009. PMID 27639967.

Bibliography

Miyazaki, M. (2000). "The Biosynthesis of Hepatic Cholesterol Esters and Triglycerides Is Impaired in Mice with a Disruption of the Gene for Stearoyl-CoA Desaturase 1". Journal of Biological Chemistry. 275 (39): 30132–30138. doi:10.1074/jbc.M005488200. PMID 10899171.

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[Ntambi20022-1] Ntambi, J. M. (2002). "Loss of stearoyl-CoA desaturase-1 function protects mice against adiposity". Proceedings of the National Academy of Sciences. 99 (17): 11482–11486. Bibcode:2002PNAS...9911482N. doi:10.1073/pnas.132384699. ISSN 0027-8424. PMC 123282. PMID 12177411.

[2] Ntambi, James (2013). Stearoyl-CoA Desaturase Genes in Lipid Metabolism. Springer. ISBN 978-1-4614-7969-7.

[3] Igal, R. Ariel (December 2016). "Stearoyl CoA desaturase-1: New insights into a central regulator of cancer metabolism". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1861 (12): 1865–1880. doi:10.1016/j.bbalip.2016.09.009. PMID 27639967.

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