CHEBI:48635 - fumagillin

ChEBI IDCHEBI:48635
ChEBI Namefumagillin
Stars
DefinitionA meroterpenoid resulting from the formal condensation of the hydroxy group of fumagillol with the carboxylic acid group of (all-E)-deca-2,4,6,8-tetraenedioic acid. Originally isolated from the fungus Aspergillus fumigatus, it is used for the control of Nosema infection in honey bees.
Secondary ChEBI IDsCHEBI:5189, CHEBI:48534
Last Modified20 October 2022
Submitterhcourrier, Kirill Degtyarenko
DownloadsMolfile
FormulaC26H34O7
Net Charge0
Average Mass458.551
Monoisotopic Mass458.23045
SMILES[H][C@]1([C@@]2(C)O[C@]2([H])CC=C(C)C)[C@H](OC)[C@H](OC(=O)/C=C/C=C/C=C/C=C/C(=O)O)CC[C@]12CO2
InChIInChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+/t19-,20-,23-,24-,25+,26+/m1/s1
InChIKeyNGGMYCMLYOUNGM-CSDLUJIJSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antibacterial drug  A drug used to treat or prevent bacterial infections.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
methionine aminopeptidase 2 inhibitor  Any methionyl aminopeptidase inhibitor that inhibits the action of methionyl aminopeptidase 2.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Applications:
antibacterial drug  A drug used to treat or prevent bacterial infections.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
ChEBI Ontology
Outgoing Relation(s)
fumagillin (CHEBI:48635) has functional parent (all-E)-deca-2,4,6,8-tetraenedioic acid (CHEBI:49057)
fumagillin (CHEBI:48635) has functional parent fumagillol (CHEBI:324935)
fumagillin (CHEBI:48635) has role angiogenesis inhibitor (CHEBI:48422)
fumagillin (CHEBI:48635) has role antibacterial drug (CHEBI:36047)
fumagillin (CHEBI:48635) has role antimicrobial agent (CHEBI:33281)
fumagillin (CHEBI:48635) has role antiprotozoal drug (CHEBI:35820)
fumagillin (CHEBI:48635) has role fungal metabolite (CHEBI:76946)
fumagillin (CHEBI:48635) has role methionine aminopeptidase 2 inhibitor (CHEBI:73361)
fumagillin (CHEBI:48635) is a antibiotic antifungal drug (CHEBI:87113)
fumagillin (CHEBI:48635) is a carboxylic ester (CHEBI:33308)
fumagillin (CHEBI:48635) is a dicarboxylic acid monoester (CHEBI:36244)
fumagillin (CHEBI:48635) is a meroterpenoid (CHEBI:64419)
fumagillin (CHEBI:48635) is a organooxygen heterocyclic antibiotic (CHEBI:25807)
fumagillin (CHEBI:48635) is a spiro-epoxide (CHEBI:133131)
Incoming Relation(s)
fumagillin-2-yl group (CHEBI:42601) is substituent group from fumagillin (CHEBI:48635)
IUPAC Name 
(2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
INNs  Source
fumagillineChemIDplus
fumagillinumChemIDplus
fumagilinaChemIDplus
fumagilinaChEBI
Synonyms  Source
FumagillinKEGG COMPOUND
2,4,6,8-decatetraenedioic acid, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro(2,5)oct-6-yl esterChemIDplus
Brand Names  Source
FumidilChemIDplus
FugillinChemIDplus
Manual XrefsDatabases
C09668KEGG COMPOUND
DB02640DrugBank
US2652356Patent
US2803586Patent
FumagillinWikipedia
LMPR0103060003LIPID MAPS
C00003133KNApSAcK
3253DrugCentral
Registry NumbersSources
Reaxys:5360220Reaxys
CAS:23110-15-8KEGG COMPOUND
CAS:23110-15-8ChemIDplus
Citations