CHEBI:42265 - epoxomicin

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ChEBI Name epoxomicin
ChEBI ID CHEBI:42265
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C28H50N4O7
Net Charge 0
Average Mass 554.71920
Monoisotopic Mass 554.36795
InChI InChI=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
InChIKey DOGIDQKFVLKMLQ-JTHVHQAWSA-N
SMILES CC[C@H](C)[C@H](NC(=O)[C@H]([C@@H](C)CC)N(C)C(C)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)[C@@]1(C)CO1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Application(s): proteasome inhibitor
A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
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ChEBI Ontology
Outgoing 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-methylpentanamide IUPAC
Manual Xref Database
Epoxomicin Wikipedia
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Registry Number Type Source
134381-21-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10468620 PubMed citation Europe PMC
10843664 PubMed citation Europe PMC
12705480 PubMed citation Europe PMC
1468981 PubMed citation Europe PMC
25666501 PubMed citation Europe PMC
Last Modified
25 February 2015