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CHEBI:42265 - epoxomicin

ChEBI IDCHEBI:42265
ChEBI Nameepoxomicin
Stars
DefinitionA tripeptide consisting of an Ile-Ile-Thr-NH2 sequence N-substituted on the threonamide amidic nitrogen with a (2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl group and with acetyl and methyl groups on the nitrogen of the isoleucine residue distal to the threonamide; a naturally occurring selective proteasome inhibitor with anti-inflammatory activity.
Last Modified25 February 2015
DownloadsMolfile
FormulaC28H50N4O7
Net Charge0
Average Mass554.729
Monoisotopic Mass554.36795
SMILESCC[C@H](C)[C@H](NC(=O)[C@H]([C@@H](C)CC)N(C)C(C)=O)C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)[C@@]1(C)CO1)[C@@H](C)O
InChIInChI=1S/C28H50N4O7/c1-11-16(5)21(30-27(38)23(17(6)12-2)32(10)19(8)34)25(36)31-22(18(7)33)26(37)29-20(13-15(3)4)24(35)28(9)14-39-28/h15-18,20-23,33H,11-14H2,1-10H3,(H,29,37)(H,30,38)(H,31,36)/t16-,17-,18+,20-,21-,22-,23-,28+/m0/s1
InChIKeyDOGIDQKFVLKMLQ-JTHVHQAWSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Application:
proteasome inhibitor  A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
ChEBI Ontology
Outgoing Relation(s)
epoxomicin (CHEBI:42265) has role proteasome inhibitor (CHEBI:52726)
epoxomicin (CHEBI:42265) is a morpholines (CHEBI:38785)
epoxomicin (CHEBI:42265) is a tripeptide (CHEBI:47923)
IUPAC Name 
N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-{(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl}-L-threoninamide
Synonym  Source
(2R,3S)-2-[acetyl(methyl)amino]-N-[(2S,3S)-1-{[(2S,3R)-3-hydroxy-1-({(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl}amino)-1-oxobutan-2-yl]amino}-3-methyl-1-oxopentan-2-yl]-3-methylpentanamideIUPAC
Manual XrefsDatabases
EpoxomicinWikipedia
Registry NumbersSources
CAS:134381-21-8ChemIDplus
Citations