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CHEBI:180490 - beauveriolide I

Default Structure
ChEBI IDCHEBI:180490
ChEBI Namebeauveriolide I
Stars
DefinitionA cyclodepsipeptide with formula C27H41N3O5. It was originally isolated from the fungus Beauveria sp. FO-6979 during a screening program for inhibitors of lipid droplet accumulation in murine macrophages. It is an inhibitor of acyl-CoA: cholesterol acyltransferase (ACAT) and effective at reducing atherogenic lesions of the artery and heart in mouse models.
Last Modified20 September 2021
SubmitterAdnan
DownloadsMolfile
FormulaC27H41N3O5
Net Charge0
Average Mass487.641
Monoisotopic Mass487.30462
SMILESCCCC[C@H](C)[C@@H]1CC(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](C)C(=O)N[C@H](CC(C)C)C(=O)O1
InChIInChI=1S/C27H41N3O5/c1-6-7-11-18(4)23-16-24(31)29-21(15-20-12-9-8-10-13-20)26(33)28-19(5)25(32)30-22(14-17(2)3)27(34)35-23/h8-10,12-13,17-19,21-23H,6-7,11,14-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t18-,19-,21-,22+,23-/m0/s1
InChIKeyZKSLFHXTWGEITF-JIORRVSTSA-N
Species of MetaboliteComponentSourceComments
Beauveria sp. (ncbitaxon:1891652) cell suspension culture (BTO:0000221) PubMed (10092189) Strain: FO-6979
Cordyceps militaris (ncbitaxon:73501) - PubMed (31926180)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
EC 2.3.1.26 (sterol O-acyltransferase) inhibitor  An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of acyl-CoA:cholesterol acyltransferase (EC 2.3.1.26).
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.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
antiatherogenic agent  A cardiovascular drug that prevents atherogenesis, the accumulation of lipid-containing plaques on the innermost layers of the arteries. Compare with antiatherosclerotic agent.
ChEBI Ontology
Outgoing Relation(s)
beauveriolide I (CHEBI:180490) has role antiatherogenic agent (CHEBI:50855)
beauveriolide I (CHEBI:180490) has role antiatherosclerotic agent (CHEBI:145947)
beauveriolide I (CHEBI:180490) has role EC 2.3.1.26 (sterol O-acyltransferase) inhibitor (CHEBI:64696)
beauveriolide I (CHEBI:180490) has role fungal metabolite (CHEBI:76946)
beauveriolide I (CHEBI:180490) has role geroprotector (CHEBI:176497)
beauveriolide I (CHEBI:180490) is a cyclodepsipeptide (CHEBI:35213)
beauveriolide I (CHEBI:180490) is a macrocycle (CHEBI:51026)
IUPAC Name 
(3R,6S,9S,13S)-9-benzyl-13-[(2S)-hexan-2-yl]-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotridecane-2,5,8,11-tetrone
Manual XrefsDatabases
8088999ChemSpider
US2003143716Patent
Registry NumbersSources
CAS:154491-55-1ChEBI
Citations