CHEBI:66281 - TMC-89A

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ChEBI Name TMC-89A
ChEBI ID CHEBI:66281
Definition An epoxide that is oxiran-2-ylmethanol which is acylated at position 2 by an N-[(2R)-3-amino-2-methyl-3-oxopropanoyl]-L-threonyl-L-threonylleucinyl group. It is a proteasome inhibitor isolated from Streptomyces sp. TC 1087.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H36N4O9
Net Charge 0
Average Mass 488.53190
Monoisotopic Mass 488.24823
InChI InChI=1S/C21H36N4O9/c1-9(2)6-13(16(29)21(7-26)8-34-21)23-19(32)14(11(4)27)25-20(33)15(12(5)28)24-18(31)10(3)17(22)30/h9-15,26-28H,6-8H2,1-5H3,(H2,22,30)(H,23,32)(H,24,31)(H,25,33)/t10-,11-,12-,13?,14+,15+,21?/m1/s1
InChIKey SCVCWUHUBWSKHS-CRHDNEEASA-N
SMILES CC(C)CC(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C)C(N)=O)[C@@H](C)O)[C@@H](C)O)C(=O)C1(CO)CO1
Metabolite of Species Details
Streptomyces sp. (NCBI:txid1931) of strain TC 1087 See: PubMed
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application(s): proteasome inhibitor
A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing TMC-89A (CHEBI:66281) has role antimicrobial agent (CHEBI:33281)
TMC-89A (CHEBI:66281) has role bacterial metabolite (CHEBI:76969)
TMC-89A (CHEBI:66281) has role proteasome inhibitor (CHEBI:52726)
TMC-89A (CHEBI:66281) is a dicarboxylic acid diamide (CHEBI:35779)
TMC-89A (CHEBI:66281) is a epoxide (CHEBI:32955)
TMC-89A (CHEBI:66281) is a ketone (CHEBI:17087)
TMC-89A (CHEBI:66281) is a primary alcohol (CHEBI:15734)
TMC-89A (CHEBI:66281) is a secondary alcohol (CHEBI:35681)
IUPAC Name
N-[(2R)-3-amino-2-methyl-3-oxopropanoyl]-L-threonyl-N-{1-[2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl}-L-threoninamide
Citation Waiting for Citations Type Source
11099231 PubMed citation Europe PMC
Last Modified
06 March 2014