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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:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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.
Applications:
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.
anticholesteremic drug  A substance used to lower plasma cholesterol levels.
antilipemic drug  A substance used to treat hyperlipidemia (an excess of lipids in the blood).
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