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CHEBI:34848 - mevastatin
| Formula | C23H34O5 |
| Net Charge | 0 |
| Average Mass | 390.520 |
| Monoisotopic Mass | 390.24062 |
| SMILES | [H][C@@]12C(=CCC[C@@H]1OC(=O)[C@@H](C)CC)C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1 |
| InChI | InChI=1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1 |
| InChIKey | AJLFOPYRIVGYMJ-INTXDZFKSA-N |
| Wikipedia |
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| Roles Classification |
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| Biological Roles: | antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. Penicillium metabolite Any fungal metabolite produced during a metabolic reaction in Penicillium. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor An EC 3.4.24.* (metalloendopeptidase) inhibitor that interferes with the action of anthrax lethal factor endopeptidase (EC 3.4.24.83). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme. EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme. |
| Applications: | anticholesteremic drug A substance used to lower plasma cholesterol levels. anticholesteremic drug A substance used to lower plasma cholesterol levels. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| mevastatin (CHEBI:34848) has role Penicillium metabolite (CHEBI:76964) |
| mevastatin (CHEBI:34848) has role antifungal agent (CHEBI:35718) |
| mevastatin (CHEBI:34848) has role apoptosis inducer (CHEBI:68495) |
| mevastatin (CHEBI:34848) has role EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor (CHEBI:77255) |
| mevastatin (CHEBI:34848) has role fungal metabolite (CHEBI:76946) |
| mevastatin (CHEBI:34848) is a 2-pyranones (CHEBI:75885) |
| mevastatin (CHEBI:34848) is a carboxylic ester (CHEBI:33308) |
| mevastatin (CHEBI:34848) is a hexahydronaphthalenes (CHEBI:142348) |
| mevastatin (CHEBI:34848) is a polyketide (CHEBI:26188) |
| mevastatin (CHEBI:34848) is a statin (naturally occurring) (CHEBI:87632) |
| Incoming Relation(s) |
| lovastatin (CHEBI:40303) has functional parent mevastatin (CHEBI:34848) |
| pravastatin lactone (CHEBI:145933) has functional parent mevastatin (CHEBI:34848) |
| IUPAC Name |
|---|
| (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate |
| INNs | Source |
|---|---|
| mévastatine | WHO MedNet |
| mevastatina | WHO MedNet |
| mevastatinum | WHO MedNet |
| mevastatin | WHO MedNet |
| Synonyms | Source |
|---|---|
| Mevastatin | KEGG COMPOUND |
| Compactin | KEGG COMPOUND |
| ML-236B | KEGG COMPOUND |
| ML 236 B | ChemIDplus |
| CS 500 | ChemIDplus |
| antibiotic ML 236B | ChemIDplus |
| UniProt Name | Source |
|---|---|
| mevastatin | UniProt |
| Registry Numbers | Sources |
|---|---|
| Reaxys:3630717 | Reaxys |
| CAS:73573-88-3 | KEGG COMPOUND |
| CAS:73573-88-3 | ChemIDplus |
| Citations |
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