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{{Unreferenced stub|auto=yes|date=December 2009}}
{{Chembox {{Chembox
| verifiedrevid = 443852794 | verifiedrevid = 450656813
|ImageFile=HMG coenzyme A.svg | ImageFile=HMG coenzyme A.svg
|ImageSize=300px | ImageSize=300px
| IUPACName=(9R,21S)-1--3,5,9,21-tetrahydroxy-8,8,21-trimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphatricosan-23-oic acid 3,5-dioxide
|IUPACName=(9R,21S)-1-[(2R,3S,4R,5R)-5-
| OtherNames=3-hydroxy-3-methylglutaryl CoA; 3-hydroxy-3-methylglutaryl coenzyme A
(6-amino-9H-purin-9-yl)-4-hydroxy-
|Section1={{Chembox Identifiers
3-(phosphonooxy)tetrahydrofuran-2-yl]-
| IUPHAR_ligand = 3040
3,5,9,21-tetrahydroxy-8,8,21-trimethyl-
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
10,14,19-trioxo-2,4,6-trioxa-18-thia-
11,15-diaza-3,5-diphosphatricosan-23-
oic acid 3,5-dioxide
|OtherNames=
|Section1= {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 392859 | ChemSpiderID = 392859
| InChI = 1/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1 | InChI = 1/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CABVTRNMFUVUDM-VRHQGPGLSA-N | StdInChIKey = CABVTRNMFUVUDM-VRHQGPGLSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=1553-55-5 | CASNo=1553-55-5
| PubChem = 445127 | PubChem = 445127
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 61659 | ChEBI = 61659
| SMILES = O=C(O)C(O)(C)CC(=O)SCCNC(=O)CCNC(=O)(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC3O(n2cnc1c(ncnc12)N)(O)3OP(=O)(O)O | SMILES = O=C(O)C(O)(C)CC(=O)SCCNC(=O)CCNC(=O)(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC3O(n2cnc1c(ncnc12)N)(O)3OP(=O)(O)O
| MeSHName=HMG-CoA | MeSHName=HMG-CoA
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>27</sub>H<sub>44</sub>N<sub>7</sub>O<sub>20</sub>P<sub>3</sub>S | Formula=C<sub>27</sub>H<sub>44</sub>N<sub>7</sub>O<sub>20</sub>P<sub>3</sub>S
| MolarMass=911.661 g/mol | MolarMass=911.661 g/mol
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
'''β-Hydroxy β-methylglutaryl-CoA''' ('''HMG-CoA'''), also known as '''3-hydroxy-3-methylglutaryl coenzyme A''', is an intermediate in the ] and ] pathways. It is formed from ] and ] by ]. The research of ] and ] in the 1950s at ] led to its discovery.<ref name="Classics in Indian Medicine">{{cite journal | url=http://www.nmji.in/archives/Volume-28/Issue-3/Classics-in-Indian-Medicine.pdf | title=Classics in Indian Medicine | first = Debi P. | last = Sarkar | name-list-style = vanc | journal=The National Medical Journal of India | year=2015 | issue=28 | pages=3 | url-status=dead | archive-url=https://web.archive.org/web/20160531082638/http://www.nmji.in/archives/Volume-28/Issue-3/Classics-in-Indian-Medicine.pdf | archive-date=2016-05-31 }}</ref><ref name="An outstanding scientist and a splendid human being">{{cite journal | title=An outstanding scientist and a splendid human being | first = Avadhesha | last = Surolia | name-list-style = vanc | author-link = Avadhesha Surolia | journal=Glycobiology | year=1997 | volume=7 | issue=4 | pages=v–ix | doi = 10.1093/glycob/7.4.453| doi-access=free }}</ref>
'''HMG-CoA''' (or '''3-hydroxy-3-methylglutaryl-coenzyme A''') is an intermediate in the ]. It is formed from ] and ] by ].


HMG-CoA is a ] in the ] of the ]s, which include ], ], and ].<ref name="HMG biosynthesis">{{cite web|title=Valine, leucine and isoleucine degradation - Reference pathway|url=http://www.genome.jp/kegg-bin/show_pathway?map00280+C00356|website=Kyoto Encyclopedia of Genes and Genomes|publisher=Kanehisa Laboratories|date=27 January 2016|access-date=1 February 2018}}</ref> Its immediate precursors are ] (MG-CoA) and ] (HMB-CoA).<ref name="ISSN position stand 2013" /><ref name="HMB athletic performance-related effects 2011 review">{{cite journal | vauthors = Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH | title = HMB supplementation: clinical and athletic performance-related effects and mechanisms of action | journal = Amino Acids | volume = 40 | issue = 4 | pages = 1015–1025 | date = April 2011 | pmid = 20607321 | doi = 10.1007/s00726-010-0678-0 | s2cid = 11120110 | url = https://repositorio.unal.edu.co/handle/unal/77957 | quote = HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, may follow one of two pathways. In the first, HMB is produced from by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).<!--<br /><br /> In the second pathway, after transamination, in liver generates isovaleryl-CoA through the enzymatic action of branched-chain ketoacid dehydrogenase (BCKD) and after several steps, there is production of HMG-CoA through the enzyme HMG-CoA synthase (Fig. 1). Under normal conditions the majority of KIC is converted into isovaleryl-CoA, in which approximately 5% of leucine is metabolized into HMB (Wilson et al. 2008; Van Koverin and Nissen 1992). However, Nissen and Abumrad (1997) provided evidence that the primary fate of HMB is probably conversion to HMG-CoA in the liver, for cholesterol biosynthesis.--> }}</ref><ref name="Leucine metabolism" />
] converts it into ].


] catalyzes the conversion of HMG-CoA to ], a necessary step in the biosynthesis of cholesterol.
]


== Biosynthesis ==
Also, ] breaks it into ] and ].
{{Leucine metabolism in humans|align=center}}


== Mevalonate pathway ==
]]]
{{main|Mevalonate pathway}}
] synthesis begins with the ]-catalyzed ] of two molecules of ] to produce ]. The following reaction involves the joining of ] and ] to form HMG-CoA, a process catalyzed by ].<ref>{{Cite book|title=Biochemistry|last=Garrett|first=Reginald H. | name-list-style = vanc |publisher=Cengage Learning|year=2013|isbn=978-1-305-57720-6|pages=856}}</ref>


In the final step of ] biosynthesis, ], an ]-dependent ], catalyzes the conversion of HMG-CoA into ], which is the primary regulatory point in this pathway. ] serves as the precursor to ] groups that are incorporated into a wide variety of end-products, including ] in humans.<ref>{{cite journal | vauthors = Haines BE, Steussy CN, Stauffacher CV, Wiest O | title = Molecular modeling of the reaction pathway and hydride transfer reactions of HMG-CoA reductase | journal = Biochemistry | volume = 51 | issue = 40 | pages = 7983–95 | date = October 2012 | pmid = 22971202 | pmc = 3522576 | doi = 10.1021/bi3008593 }}</ref>
It is also an intermediate in the metabolism of ]. Its immediate precursor is ].

]
{{Clear}}

== Ketogenesis pathway ==
] breaks it into ] and ].

]]]
{{Clear}}

== See also ==
* ]

== References ==
{{Reflist}}


{{Cholesterol metabolism intermediates}} {{Cholesterol metabolism intermediates}}
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{{DEFAULTSORT:Hmg-Coa}} {{DEFAULTSORT:Hmg-Coa}}
] ]
]




{{Biochemistry-stub}} {{Biochemistry-stub}}

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