CHEBI:180490 - beauveriolide I

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ChEBI Name beauveriolide I
ChEBI ID CHEBI:180490
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C27H41N3O5
Net Charge 0
Average Mass 487.641
Monoisotopic Mass 487.30462
InChI InChI=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
InChIKey ZKSLFHXTWGEITF-JIORRVSTSA-N
SMILES CCCC[C@H](C)[C@@H]1CC(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](C)C(=O)N[C@H](CC(C)C)C(=O)O1
Metabolite of Species Details
Beauveria sp. (NCBI:txid1891652) Found in cell suspension culture (BTO:0000221). of strain FO-6979 See: PubMed
Cordyceps militaris (NCBI:txid73501) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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 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).
Application(s): 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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Xrefs Databases
8088999 ChemSpider
US2003143716 Patent
View more database links
Registry Number Type Source
154491-55-1 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
10092189 PubMed citation Europe PMC
12617514 PubMed citation Europe PMC
14718664 PubMed citation Europe PMC
17803269 PubMed citation Europe PMC
18620856 PubMed citation Europe PMC
19396893 PubMed citation Europe PMC
22079027 PubMed citation Europe PMC
22790951 PubMed citation Europe PMC
23252879 PubMed citation Europe PMC
31926180 PubMed citation Europe PMC
324779 Chinese Abstracts citation Europe PMC
Last Modified
20 September 2021