HMG-CoA

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HMG-CoA
Names
IUPAC name
(9R,21S)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-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
Other names
3-hydroxy-3-methylglutaryl CoA; 3-hydroxy-3-methylglutaryl coenzyme A
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.014.820 Edit this at Wikidata
IUPHAR/BPS
MeSH HMG-CoA
  • InChI=1S/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 checkY
    Key: CABVTRNMFUVUDM-VRHQGPGLSA-N checkY
  • 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
    Key: CABVTRNMFUVUDM-VRHQGPGLBX
  • O=C(O)C[C@@](O)(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
C27H44N7O20P3S
Molar mass 911.661 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

β-Hydroxy β-methylglutaryl-CoA (HMG-CoA), also known as 3-hydroxy-3-methylglutaryl coenzyme A, is an intermediate in the

University of Illinois led to its discovery.[1][2]

HMG-CoA is a

β-hydroxy β-methylbutyryl-CoA (HMB-CoA).[4][5][6]

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

Biosynthesis

Diagram of leucine, HMB, and isovaleryl-CoA metabolism in humans
α-Ketoglutarate
Glutamate
Glutamate
Pyruvate
α-Ketoisocaproate
(α-KIC)
α-Ketoisocaproate
(α-KIC)
mitochondria
)
Excreted
in urine
(10–40%)


β-Hydroxy β-methylglutaryl-CoA
(HMG-CoA)
(
HMG-CoA
lyase
HMG-CoA 
synthase
Unknown
enzyme
β-Hydroxybutyrate
Acetoacetate
Mevalonate
The image above contains clickable links
Human metabolic pathway for HMB and isovaleryl-CoA relative to L-leucine.[4][7][6] Of the two major pathways, L-leucine is mostly metabolized into isovaleryl-CoA, while only about 5% is metabolized into HMB.[4][7][6]

Mevalonate pathway

Main article: Mevalonate pathway

HMG-CoA synthase.[8]

In the final step of

isoprenoid groups that are incorporated into a wide variety of end-products, including cholesterol in humans.[9]

Mevalonate pathway

Ketogenesis pathway

acetoacetate
.

Ketogenesis

See also

References

  1. ^ Sarkar DP (2015). "Classics in Indian Medicine" (PDF). The National Medical Journal of India (28): 3. Archived from the original (PDF) on 2016-05-31.
  2. doi:10.1093/glycob/7.4.453
    .
  3. ^ "Valine, leucine and isoleucine degradation - Reference pathway". Kyoto Encyclopedia of Genes and Genomes. Kanehisa Laboratories. 27 January 2016. Retrieved 1 February 2018.
  4. ^
    PMID 23374455
    .
  5. ^
    ISBN 978-0-12-387784-0. Retrieved 6 June 2016. Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds
    Figure 8.57: Metabolism of L-leucine
  6. ISBN 978-1-305-57720-6
    .
  7. PMID 22971202
    .


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