CHEBI:50130 - monacolin L

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ChEBI Name monacolin L
ChEBI ID CHEBI:50130
Definition A polyketide that is 1-ethyl-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalene in which one of the methyl hydrogens from the ethyl group is replaced by a 4-hydroxy-6-ketopyran-2-yl group.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Secondary ChEBI IDs CHEBI:79043
Supplier Information
Download Molfile XML SDF
Formula C19H28O3
Net Charge 0
Average Mass 304.42380
Monoisotopic Mass 304.20384
InChI InChI=1S/C19H28O3/c1-12-3-7-18-14(9-12)5-4-13(2)17(18)8-6-16-10-15(20)11-19(21)22-16/h4-5,9,12-13,15-18,20H,3,6-8,10-11H2,1-2H3/t12-,13+,15-,16-,17+,18+/m1/s1
InChIKey BKZPCUPKVCPRQW-MHMDBQTNSA-N
SMILES C[C@@H]1CC[C@@H]2[C@@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@@H](C)C=CC2=C1
Metabolite of Species Details
Aspergillus terreus (NCBI:txid33178) of strain ATCC 20542 See: PubMed
Monascus ruber (NCBI:txid89489) of strain M 4681 See: PubMed
Roles Classification
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
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.
Application(s): anticholesteremic drug
A substance used to lower plasma cholesterol levels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing monacolin L (CHEBI:50130) has role Aspergillus metabolite (CHEBI:76956)
monacolin L (CHEBI:50130) has role anticholesteremic drug (CHEBI:35821)
monacolin L (CHEBI:50130) has role EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor (CHEBI:35664)
monacolin L (CHEBI:50130) is a 2-pyranones (CHEBI:75885)
monacolin L (CHEBI:50130) is a hexahydronaphthalenes (CHEBI:142348)
monacolin L (CHEBI:50130) is a polyketide (CHEBI:26188)
monacolin L (CHEBI:50130) is a secondary alcohol (CHEBI:35681)
Incoming dihydromonacolin L (CHEBI:14158) has functional parent monacolin L (CHEBI:50130)
monacolin J (CHEBI:79034) has functional parent monacolin L (CHEBI:50130)
monacolin L acid (CHEBI:82987) has functional parent monacolin L (CHEBI:50130)
IUPAC Name
(4R,6R)-6-{2-[(1S,2S,6R,8aR)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-hydroxyoxan-2-one
Synonyms Sources
(4R,6R)-6-{2-[(1S,2S,6R,8aR)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-hydroxytetrahydro-2H-pyran-2-one IUPAC
monacolin L lactone ChEBI
Manual Xrefs Databases
C00018633 KNApSAcK
KR20040016648 Patent
View more database links
Registry Numbers Types Sources
79394-47-1 CAS Registry Number ChemIDplus
8791298 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
21495633 PubMed citation SUBMITTER
22995742 PubMed citation Europe PMC
24534845 PubMed citation Europe PMC
2708134 PubMed citation Europe PMC
2921224 PubMed citation SUBMITTER
Last Modified
23 September 2018