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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. fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. Penicillium metabolite Any fungal metabolite produced during a metabolic reaction in Penicillium. 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). apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. 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 |
|---|---|
| mevastatin | WHO MedNet |
| mevastatina | WHO MedNet |
| mévastatine | WHO MedNet |
| mevastatinum | WHO MedNet |
| Synonyms | Source |
|---|---|
| antibiotic ML 236B | ChemIDplus |
| Compactin | KEGG COMPOUND |
| CS 500 | ChemIDplus |
| Mevastatin | KEGG COMPOUND |
| ML 236 B | ChemIDplus |
| ML-236B | KEGG COMPOUND |
| 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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