β-Hydroxy β-methylbutyryl-coenzyme A (HMB-CoA), also known as 3-hydroxyisovaleryl-CoA, is a metabolite of l-leucine that is produced in the human body.[1][2] Its immediate precursors are β-hydroxy β-methylbutyric acid (HMB) and β-methylcrotonoyl-CoA (MC-CoA). It can be metabolized into HMB, MC-CoA, and HMG-CoA in humans.
β-Hydroxy β-methylbutyryl-CoA |
| Names |
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| IUPAC name S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 3-hydroxy-3-methylbutanethioate |
| Other names β-hydroxyisovaleryl-CoA
3-hydroxyisovaleryl-CoA
3-hydroxy-3-methylbutyryl-CoA |
| Identifiers |
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3D model (JSmol) | |
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SMILES CC(C)(CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)OP(=O)(O)O)O)O
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| Properties |
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Chemical formula | C26H44N7O18P3S |
| Molar mass | 867.649946 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
| Infobox references |
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Metabolic pathwayEditMuscle: α-Ketoisocaproate (α-KIC) Liver: α-Ketoisocaproate (α-KIC) Branched-chain α-ketoacid
dehydrogenase (mitochondria) KIC-dioxygenase
(cytosol) β-Hydroxy
β-methylbutyrate
(HMB) Excreted
in urine
(10–40%)
HMB-CoA β-Hydroxy β-methylglutaryl-CoA
(HMG-CoA) β-Methylcrotonyl-CoA
(MC-CoA) β-Methylglutaconyl-CoA
(MG-CoA) (liver)
HMG-CoA
lyase Unknown
enzyme Human metabolic pathway for HMB and isovaleryl-CoA relative to l-leucine. [1][5][2] Of the two major pathways, l-leucine is mostly metabolized into isovaleryl-CoA, while only about 5% is metabolized into HMB. [1][5][
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