(S)-3-Hydroxy-3-methylglutaryl-CoA (BioCAD00000000937)
Metabolite Card
Formula: C27H44N7O20P3S (911.1575)
SMILES: C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
Synonyms [en]
(S)-3-hydroxy-3-methylglutaryl-CoA; Hydroxymethylglutaroyl coenzyme A; 3-hydroxy-3-methylglutaryl-CoA; hydroxymethylglutaryl-CoA; HMG-CoA; HMG-coenzyme A
Last reviewed on 2024-06-28.
Cite this Page
(S)-3-Hydroxy-3-methylglutaryl-CoA. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000000937). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
3-Hydroxy-3-methylglutaryl-CoA (HMG-CoA) (CAS: 1553-55-5) is formed when acetyl-CoA condenses with acetoacetyl-CoA in a reaction that is catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway or mevalonate-dependent (MAD) route, an important cellular metabolic pathway present in virtually all organisms. HMG-CoA reductase (EC 1.1.1.34) inhibitors, more commonly known as statins, are cholesterol-lowering drugs that have been widely used for many years to reduce the incidence of adverse cardiovascular events. HMG-CoA reductase catalyzes the rate-limiting step in the mevalonate pathway and these agents lower cholesterol by inhibiting its synthesis in the liver and in peripheral tissues. Androgen also stimulates lipogenesis in human prostate cancer cells directly by increasing transcription of the fatty acid synthase and HMG-CoA-reductase genes (PMID: 14689582).
DBLinks
- CAS Registry Number: 1553-55-5
- PubChem CID: 445127
- ChEBI: 15467
- HMDB: HMDB0001375
- LipidMaps: LMFA07050209
- KEGG: C00356
- BioCyc:
- NCBI MeSH: 3-hydroxy-3-methylglutaryl-coenzyme A
- Wikipedia: HMG-CoA
Other DBLinks
- CAS Registry Number: 1553-55-5
- CAS Registry Number: 26926-09-0
- PubChem: 445127
- PubChem: 91506
- ChEBI: ChEBI:11814
- ChEBI: ChEBI:15467
- HMDB: HMDB0001375
- HMDB: HMDB01375
- LipidMaps: LMFA07050116
- LipidMaps: LMFA07050209
- KEGG: C00356
- NCBI MeSH: 3-hydroxy-3-methylglutaryl-coenzyme A
- Wikipedia: HMG-CoA
- RefMet: RM0160240
- Metlin: METLIN_349
- Coconut NaturalProduct: CNP0085565.2
- Coconut NaturalProduct: CNP0085565.3
Class / Ontology
- WishartLab ClassyFire: [Fatty acyl thioesters] Fatty acyl thioesters
- RefMet: [Acyl CoAs] Acyl CoAs
- LipidMaps: [Fatty acyl CoAs [FA0705]] Fatty acyl CoAs [FA0705]
- ChEBI: [CHEBI:15467] (3S)-3-hydroxy-3-methylglutaryl-CoA
- Coconut NaturalProduct: [Fatty acyl CoAs] Fatty acyl CoAs
| ID | EC Number | Name |
|---|---|---|
| KEGG:R01360 | 4.1.3.4 | (S)-3-hydroxy-3-methylglutaryl-CoA acetoacetate-lyase (acetyl-CoA-forming) |
| KEGG:R01978 | 2.3.3.10 | acetyl-CoA:acetoacetyl-CoA C-acetyltransferase (thioester-hydrolysing, carboxymethyl-forming) |
| KEGG:R02081 | 1.1.1.88 | (R)-mevalonate:NAD+ oxidoreductase (CoA-acetylating) |
| KEGG:R02082 | 1.1.1.34 | (R)-mevalonate:NADP+ oxidoreductase (CoA acylating) |
| KEGG:R02083 | 3.1.2.5 | (S)-3-hydroxy-3-methylglutaryl-CoA hydrolase |
| KEGG:R02084 | 2.8.3.13 | succinyl-CoA:3-hydroxy-3-methylglutarate CoA-transferase |
| KEGG:R02085 | 4.2.1.18 | (S)-3-hydroxy-3-methylglutaryl-CoA hydro-lyase (trans-3-methylglutaconyl-CoA-forming) |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:TRYPANO_PWY-922 | mevalonate pathway I |
| BioCyc:LEISH_PWY-922 | mevalonate pathway I |
| BioCyc:LEISH_LEU-DEG2-PWY | leucine degradation I |
| BioCyc:TRYPANO_LEU-DEG2-PWY | leucine degradation I |
| BioCyc:LEISH_PWY3IU-93 | superpathway of sterol biosynthesis |
| Plant Reactome:R-OAU-2744345 | Metabolism and regulation |
| Plant Reactome:R-OAU-1119615 | MVA pathway |
| Plant Reactome:R-TAE-2744344 | Secondary metabolism |
| Plant Reactome:R-FVE-1119615 | MVA pathway |
| Plant Reactome:R-MES-2744345 | Metabolism and regulation |
| Plant Reactome:R-MES-1119615 | MVA pathway |
| Plant Reactome:R-TDI-2744345 | Metabolism and regulation |
| Plant Reactome:R-DRO-2744345 | Metabolism and regulation |
| Plant Reactome:R-DRO-1119615 | MVA pathway |
| Plant Reactome:R-GSU-2744344 | Secondary metabolism |
| Plant Reactome:R-PTI-2744345 | Metabolism and regulation |
| Plant Reactome:R-GMA-2744345 | Metabolism and regulation |
| Plant Reactome:R-GMA-2744344 | Secondary metabolism |
| Plant Reactome:R-PDA-2744345 | Metabolism and regulation |
| Plant Reactome:R-PDA-1119615 | MVA pathway |