CHEBI:34652 - compactin diol lactone

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name compactin diol lactone
ChEBI ID CHEBI:34652
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C18H26O4
Net Charge 0
Average Mass 306.402
Monoisotopic Mass 306.18311
InChI InChI=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
InChIKey WWSNTLOVYSRDEL-DZSDEGEFSA-N
SMILES C1CC=C2[C@]([C@H]1O)([C@H]([C@H](C=C2)C)CC[C@H]3OC(C[C@@H](C3)O)=O)[H]
Metabolite of Species Details
Penicillium citrinum (NCBI:txid5077) Found in cell suspension culture (BTO:0000221). of strain SANK 18767 See: PubMed
Roles Classification
Biological Role(s): 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.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application(s): antilipemic drug
A substance used to treat hyperlipidemia (an excess of lipids in the blood).
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(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-one IUPAC
Antibiotic ML 236A ChEBI
compactin diol lactone KEGG COMPOUND
compactin diol lactone UniProt
desmethylmonacolin J ChEBI
ML 236A ChemIDplus
ML-236A KEGG COMPOUND
Manual Xrefs Databases
C00018116 KNApSAcK
C14183 KEGG COMPOUND
View more database links
Registry Number Type Source
58889-19-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1010803 PubMed citation Europe PMC
12929390 PubMed citation Europe PMC
15531273 PubMed citation Europe PMC
16386050 PubMed citation Europe PMC
2280672 PubMed citation Europe PMC
2696346 PubMed citation Europe PMC
28619444 PubMed citation Europe PMC
3793626 PubMed citation Europe PMC
6549610 PubMed citation Europe PMC
908337 PubMed citation Europe PMC
Last Modified
30 January 2020
General Comment
2020-01-30 Total synthesis of this compound is described in the following article: Danishefsky, S.J. and Simoneau. (1989) Total syntheses of ML-236A and compactin by combining the lactonic (silyl) enolate rearrangement and aldehyde-diene cyclocondensation technologies. J. Am. Chem. Soc., 111(7), 2599-2604.