CHEBI:34848 - mevastatin

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ChEBI Name mevastatin
ChEBI ID CHEBI:34848
Definition A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5418550, eMolecules:531093, ZINC000004081043
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Dihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups, and therefore is a dithiol. It is optically active, but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.
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Formula C23H34O5
Net Charge 0
Average Mass 390.51310
Monoisotopic Mass 390.24062
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
SMILES CC[C@H](C)C(=O)O[C@H]1CCC=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@@H]12
Roles Classification
Biological Role(s): 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).
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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via statin (naturally occurring) )
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.
(via statin )
Application(s): anticholesteremic drug
A substance used to lower plasma cholesterol levels.
(via statin )
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ChEBI Ontology
Outgoing 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 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 Sources
mevastatin WHO MedNet
mevastatina WHO MedNet
mévastatine WHO MedNet
mevastatinum WHO MedNet
Synonyms Sources
antibiotic ML 236B ChemIDplus
Compactin KEGG COMPOUND
CS 500 ChemIDplus
mevastatin UniProt
Mevastatin KEGG COMPOUND
ML 236 B ChemIDplus
ML-236B KEGG COMPOUND
Manual Xrefs Databases
C00000564 KNApSAcK
C13963 KEGG COMPOUND
DB06693 DrugBank
DE2524355 Patent
LSM-4123 LINCS
Mevastatin Wikipedia
US3983140 Patent
View more database links
Registry Numbers Types Sources
3630717 Reaxys Registry Number Reaxys
73573-88-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11283400 PubMed citation Europe PMC
12403272 PubMed citation Europe PMC
15274361 PubMed citation Europe PMC
15531285 PubMed citation Europe PMC
15786722 PubMed citation Europe PMC
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18936176 PubMed citation Europe PMC
20629200 PubMed citation Europe PMC
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3170348 PubMed citation Europe PMC
3719857 PubMed citation Europe PMC
Last Modified
23 September 2018