CHEBI:79034 - monacolin J

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ChEBI Name monacolin J
ChEBI ID CHEBI:79034
Definition A polyketide that is monacolin L bearing an additional hydroxy substituent at position 8.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
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Formula C19H28O4
Net Charge 0
Average Mass 320.42320
Monoisotopic Mass 320.19876
InChI InChI=1S/C19H28O4/c1-11-7-13-4-3-12(2)16(19(13)17(21)8-11)6-5-15-9-14(20)10-18(22)23-15/h3-4,7,11-12,14-17,19-21H,5-6,8-10H2,1-2H3/t11-,12-,14+,15+,16-,17-,19-/m0/s1
InChIKey ZDFOBOYQVYMVCW-IRUSZSJRSA-N
SMILES C[C@@H]1C[C@H](O)[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
Monascus ruber (NCBI:txid89489) See: PubMed
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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.
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ChEBI Ontology
Outgoing monacolin J (CHEBI:79034) has functional parent monacolin L (CHEBI:50130)
monacolin J (CHEBI:79034) has role antimicrobial agent (CHEBI:33281)
monacolin J (CHEBI:79034) has role EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor (CHEBI:35664)
monacolin J (CHEBI:79034) has role fungal metabolite (CHEBI:76946)
monacolin J (CHEBI:79034) is a 2-pyranones (CHEBI:75885)
monacolin J (CHEBI:79034) is a carbobicyclic compound (CHEBI:36785)
monacolin J (CHEBI:79034) is a hexahydronaphthalenes (CHEBI:142348)
monacolin J (CHEBI:79034) is a polyketide (CHEBI:26188)
monacolin J (CHEBI:79034) is a secondary alcohol (CHEBI:35681)
Incoming monacolin J acid (CHEBI:82971) has functional parent monacolin J (CHEBI:79034)
IUPAC Name
(4R,6R)-4-hydroxy-6-{2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}tetrahydro-2H-pyran-2-one
Synonyms Sources
Antibiotic MB 530A KNApSAcK
Lovastatin diol lactone KNApSAcK
Monacolin J KNApSAcK
monacolin J UniProt
monacolin J lactone ChEBI
Manual Xrefs Databases
C00018632 KNApSAcK
Monacolin_J Wikipedia
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Registry Numbers Types Sources
4758897 Reaxys Registry Number Reaxys
79952-42-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20648024 PubMed citation Europe PMC
21495633 PubMed citation SUBMITTER
2276983 PubMed citation Europe PMC
2708134 PubMed citation Europe PMC
3839227 PubMed citation Europe PMC
Last Modified
28 January 2020