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fumagillin

Go to external page http://purl.obolibrary.org/obo/CHEBI_48635

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.

Term info

Label

fumagillin

Synonyms
  • (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
  • Fumagillin
database cross reference
Subsets

3_STAR

INN
fumagilina [ ChemIDplus ]

BRAND NAME
Fugillin [ ChemIDplus ]

INN
fumagillinum [ ChemIDplus ]

INN
fumagilline [ ChemIDplus ]

BRAND NAME
Fumidil [ ChemIDplus ]

INN
fumagilina [ ChEBI ]

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 [ IUPAC ]

charge

0

formula

C26H34O7

has alternative id

CHEBI:5189, CHEBI:48534

has obo namespace

chebi_ontology

has related synonym

Fumidil, fumagilline, fumagillinum, fumagilina, 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, Fugillin

id

CHEBI:48635

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

mass

458.545

monoisotopicmass

458.23045

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