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CHEBI:50130 - monacolin L

ChEBI IDCHEBI:50130
ChEBI Namemonacolin L
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:79043
Last Modified23 September 2018
SubmitterKristian Axelsen, Marcus Ennis
DownloadsMolfile
FormulaC19H28O3
Net Charge0
Average Mass304.430
Monoisotopic Mass304.20384
SMILES[H][C@]12CC[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1
InChIInChI=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
InChIKeyBKZPCUPKVCPRQW-MHMDBQTNSA-N
Species of MetaboliteComponentSourceComments
Monascus ruber (ncbitaxon:89489) - PubMed (3839227) Strain: M 4681
Aspergillus terreus (ncbitaxon:33178) - PubMed (24534845) Strain: ATCC 20542
Roles Classification
Biological Roles:
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.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
Application:
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
(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-oneIUPAC
monacolin L lactoneChEBI
Manual XrefsDatabases
C00018633KNApSAcK
KR20040016648Patent
Registry NumbersSources
Reaxys:8791298Reaxys
CAS:79394-47-1ChemIDplus
Citations