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CHEBI:3000 - beauvericin

ChEBI IDCHEBI:3000
ChEBI Namebeauvericin
Stars
DefinitionA trimeric cyclodepsipeptide composed from alternating methylphenylalanyl and hydroxyvaleryl residues.
Last Modified15 October 2019
DownloadsMolfile
FormulaC45H57N3O9
Net Charge0
Average Mass783.963
Monoisotopic Mass783.40948
SMILESCC(C)[C@H]1OC(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](Cc2ccccc2)N(C)C1=O
InChIInChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1
InChIKeyGYSCAQFHASJXRS-FFCOJMSVSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Beauveria bassiana (ncbitaxon:176275) - PubMed (18804027)
Fusarium proliferatum (ncbitaxon:948311) - PubMed (23832252)
Fusarium equiseti (ncbitaxon:61235) - PubMed (25475336)
Fusarium poae (ncbitaxon:36050) - PubMed (25475336)
Fusarium avenaceum (ncbitaxon:40199) - PubMed (25475336)
Fusarium sporotrichioides (ncbitaxon:5514) - PubMed (25475336)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
apoptosis inhibitor  Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
mycotoxin  Poisonous substance produced by fungi.
P450 inhibitor  An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
ionophore  A compound which can carry specific ions through membranes of cells or organelles.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
beauvericin (CHEBI:3000) has role antibiotic insecticide (CHEBI:39208)
beauvericin (CHEBI:3000) has role antifungal agent (CHEBI:35718)
beauvericin (CHEBI:3000) has role antineoplastic agent (CHEBI:35610)
beauvericin (CHEBI:3000) has role apoptosis inhibitor (CHEBI:68494)
beauvericin (CHEBI:3000) has role fungal metabolite (CHEBI:76946)
beauvericin (CHEBI:3000) has role ionophore (CHEBI:24869)
beauvericin (CHEBI:3000) has role mycotoxin (CHEBI:25442)
beauvericin (CHEBI:3000) has role P450 inhibitor (CHEBI:50183)
beauvericin (CHEBI:3000) is a cyclodepsipeptide (CHEBI:35213)
IUPAC Name 
(3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Synonyms  Source
BeauvericinKEGG COMPOUND
(3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexoneIUPAC
UniProt Name  Source
beauvericinUniProt
Manual XrefsDatabases
C11590KEGG COMPOUND
C00027924KNApSAcK
BeauvericinWikipedia
Registry NumbersSources
Reaxys:5223711Reaxys
Reaxys:24193536Reaxys
CAS:26048-05-5KEGG COMPOUND
CAS:26048-05-5ChemIDplus
Citations