CHEBI:48635 - fumagillin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name fumagillin
ChEBI ID CHEBI:48635
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:48534, CHEBI:5189
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formulae C26H34O7
C26H34O7
Net Charge 0
Average Mass 458.545
Monoisotopic Mass 458.230
InChI InChI=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
InChIKey NGGMYCMLYOUNGM-CSDLUJIJSA-N
SMILES [C@]1([C@]2(O[C@@]2(CC=C(C)C)[H])C)([H])[C@H](OC)[C@@H](CC[C@]13CO3)OC(/C=C/C=C/C=C/C=C/C(=O)O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
antibacterial drug
A drug used to treat or prevent bacterial infections.
methionine aminopeptidase 2 inhibitor
Any methionyl aminopeptidase inhibitor that inhibits the action of methionyl aminopeptidase 2.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via meroterpenoid )
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via antibiotic antifungal agent )
Application(s): angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
antibacterial drug
A drug used to treat or prevent bacterial infections.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via antibiotic antifungal drug )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
fumagilina ChemIDplus
fumagilina ChEBI
fumagilline ChemIDplus
fumagillinum ChemIDplus
Synonyms Sources
2,4,6,8-decatetraenedioic acid, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro(2,5)oct-6-yl ester ChemIDplus
Fumagillin KEGG COMPOUND
Brand Names Sources
Fugillin ChemIDplus
Fumidil ChemIDplus
Manual Xrefs Databases
3253 DrugCentral
C00003133 KNApSAcK
C09668 KEGG COMPOUND
DB02640 DrugBank
Fumagillin Wikipedia
LMPR0103060003 LIPID MAPS
US2652356 Patent
US2803586 Patent
View more database links
Registry Numbers Types Sources
23110-15-8 CAS Registry Number KEGG COMPOUND
23110-15-8 CAS Registry Number ChemIDplus
5360220 Beilstein Registry Number Beilstein
5360220 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
14514693 PubMed citation Europe PMC
14809278 PubMed citation Europe PMC
15723631 PubMed citation Europe PMC
23121865 PubMed citation Europe PMC
23488861 PubMed citation Europe PMC
23505365 PubMed citation Europe PMC
Last Modified
22 February 2017