HMG-CoA

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HMG-CoA
HMG coenzyme A.svg
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
Identifiers
1553-55-5 YesY
ChEBI CHEBI:61659 YesY
ChemSpider 392859 YesY
3040
Jmol 3D model Interactive image
MeSH HMG-CoA
PubChem 445127
  • 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 YesY
    Key: CABVTRNMFUVUDM-VRHQGPGLSA-N YesY
  • 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
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

HMG-CoA (or 3-hydroxy-3-methylglutaryl-coenzyme A) is an intermediate in the mevalonate and ketogenesis pathways. It is formed from acetyl CoA and acetoacetyl CoA by HMG-CoA synthase.

It is also an intermediate in the metabolism of leucine. Its immediate precursor is 3-methylglutaconyl CoA.

Mevalonate pathway

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HMG-CoA reductase converts it into mevalonic acid.

Mevalonate pathway

Ketogenesis pathway

HMG-CoA lyase breaks it into acetyl CoA and acetoacetate.

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