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CHEBI:66281 - TMC-89A

ChEBI IDCHEBI:66281
ChEBI NameTMC-89A
Stars
DefinitionAn 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.
Last Modified6 March 2014
DownloadsMolfile
FormulaC21H36N4O9
Net Charge0
Average Mass488.538
Monoisotopic Mass488.24823
SMILESCC(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
InChIInChI=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
InChIKeySCVCWUHUBWSKHS-CRHDNEEASA-N
Species of MetaboliteComponentSourceComments
Streptomyces sp. (ncbitaxon:1931) - PubMed (11099231) Strain: TC 1087
Roles Classification
Biological Roles:
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:
proteasome inhibitor  A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
ChEBI Ontology
Outgoing Relation(s)
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
Citations