CHEBI:40303 - lovastatin

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ChEBI Name lovastatin
ChEBI ID CHEBI:40303
Definition A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40299, CHEBI:6544
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Formula C24H36O5
Net Charge 0
Average Mass 404.53964
Monoisotopic Mass 404.256
InChI InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKey PCZOHLXUXFIOCF-BXMDZJJMSA-N
SMILES [H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)[C@@H](C)CC
Roles Classification
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
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): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
anticholesteremic drug
A substance used to lower plasma cholesterol levels.
(via statin )
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing lovastatin (CHEBI:40303) has functional parent (S)-2-methylbutyric acid (CHEBI:38655)
lovastatin (CHEBI:40303) has functional parent mevastatin (CHEBI:34848)
lovastatin (CHEBI:40303) has role Aspergillus metabolite (CHEBI:76956)
lovastatin (CHEBI:40303) has role anticholesteremic drug (CHEBI:35821)
lovastatin (CHEBI:40303) has role antineoplastic agent (CHEBI:35610)
lovastatin (CHEBI:40303) has role prodrug (CHEBI:50266)
lovastatin (CHEBI:40303) is a δ-lactone (CHEBI:18946)
lovastatin (CHEBI:40303) is a carbobicyclic compound (CHEBI:36785)
lovastatin (CHEBI:40303) is a fatty acid ester (CHEBI:35748)
lovastatin (CHEBI:40303) is a polyketide (CHEBI:26188)
lovastatin (CHEBI:40303) is a statin (naturally occurring) (CHEBI:87632)
Incoming mevinolinic acid (CHEBI:82985) has functional parent lovastatin (CHEBI:40303)
simvastatin (CHEBI:9150) has functional parent lovastatin (CHEBI:40303)
IUPAC Name
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
Synonyms Sources
(1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyrate ChemIDplus
2β,6α-dimethyl-8alpha-(2-methyl-1-oxobutoxy)-mevinic acid lactone ChemIDplus
6α-methylcompactin ChemIDplus
Lovastatin KEGG COMPOUND
LOVASTATIN PDBeChem
Mevinolin ChemIDplus
MK-803 KEGG DRUG
ML-530B KEGG DRUG
Brand Name Source
Mevacor ChemIDplus
Database Links Databases
803 PDBeChem
C00000547 KNApSAcK
C07074 KEGG COMPOUND
CN103172602 Patent
D00359 KEGG DRUG
DB00227 DrugBank
HMDB14372 HMDB
Lovastatin Wikipedia
LSM-2189 LINCS
WO2013090461 Patent
View more database links
Registry Numbers Types Sources
3631989 Beilstein Registry Number ChemIDplus
4720754 Reaxys Registry Number Reaxys
75330-75-5 CAS Registry Number ChemIDplus
75330-75-5 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
11375168 PubMed citation Europe PMC
11389707 PubMed citation Europe PMC
11483865 PubMed citation Europe PMC
18642339 PubMed citation Europe PMC
24093797 PubMed citation Europe PMC
7720768 PubMed citation Europe PMC
Last Modified
24 February 2016