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CHEBI:34652 - compactin diol lactone

ChEBI IDCHEBI:34652
ChEBI Namecompactin diol lactone
Stars
DefinitionA carbobicyclic compound that is ML-236C substituted by a hydroxy group at position 8S. It is a fungal metabolite isolated from Penicillium citrinum and exhibits anticholesteremic activity.
Last Modified30 January 2020
DownloadsMolfile
FormulaC18H26O4
Net Charge0
Average Mass306.402
Monoisotopic Mass306.18311
SMILES[H][C@@]12C(=CCC[C@@H]1O)C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1
InChIInChI=1S/C18H26O4/c1-11-5-6-12-3-2-4-16(20)18(12)15(11)8-7-14-9-13(19)10-17(21)22-14/h3,5-6,11,13-16,18-20H,2,4,7-10H2,1H3/t11-,13+,14+,15-,16-,18-/m0/s1
InChIKeyWWSNTLOVYSRDEL-DZSDEGEFSA-N
Species of MetaboliteComponentSourceComments
Penicillium citrinum (ncbitaxon:5077) cell suspension culture (BTO:0000221) PubMed (1010803) Strain: SANK 18767
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.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
antilipemic drug  A substance used to treat hyperlipidemia (an excess of lipids in the blood).
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
antiatherosclerotic agent  A cardiovascular drug that prevents atherosclerosis (a disease in which the inside of an artery narrows due to the build up of plaque). Compare with antiatherogenic agent.
ChEBI Ontology
Outgoing Relation(s)
compactin diol lactone (CHEBI:34652) has functional parent ML-236C (CHEBI:34828)
compactin diol lactone (CHEBI:34652) has role antiatherosclerotic agent (CHEBI:145947)
compactin diol lactone (CHEBI:34652) has role anticholesteremic drug (CHEBI:35821)
compactin diol lactone (CHEBI:34652) has role antilipemic drug (CHEBI:35679)
compactin diol lactone (CHEBI:34652) has role antimicrobial agent (CHEBI:33281)
compactin diol lactone (CHEBI:34652) has role EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor (CHEBI:35664)
compactin diol lactone (CHEBI:34652) has role fungal metabolite (CHEBI:76946)
compactin diol lactone (CHEBI:34652) is a 2-pyranones (CHEBI:75885)
compactin diol lactone (CHEBI:34652) is a carbobicyclic compound (CHEBI:36785)
compactin diol lactone (CHEBI:34652) is a hexahydronaphthalenes (CHEBI:142348)
compactin diol lactone (CHEBI:34652) is a polyketide (CHEBI:26188)
compactin diol lactone (CHEBI:34652) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(4R,6R)-4-hydroxy-6-{2-[(1S,2S,8S,8aR)-8-hydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}tetrahydro-2H-pyran-2-one
Synonyms  Source
compactin diol lactoneKEGG COMPOUND
ML-236AKEGG COMPOUND
(4R,6R)-4-hydroxy-6-{2-[(1S,2S,8S,8aR)-8-hydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}oxan-2-oneIUPAC
ML 236AChemIDplus
Antibiotic ML 236AChEBI
desmethylmonacolin JChEBI
UniProt Name  Source
compactin diol lactoneUniProt
Manual XrefsDatabases
C14183KEGG COMPOUND
C00018116KNApSAcK
Registry NumbersSources
CAS:58889-19-3KEGG COMPOUND
CAS:58889-19-3ChemIDplus
Citations