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CHEBI:66248 - TMC-95D

ChEBI IDCHEBI:66248
ChEBI NameTMC-95D
Stars
DefinitionA 17-membered macrocyclic lactam that incorporates a phenol and a substituted indole moiety. It includes a R-hydroxy group at position 11 and a (3-methyl-2-oxopentanoyl)amino group at position at position 18 with a S-methyl group. It acts as a proteasome inhibitor and is obtained from Apiospora montagnei Sacc. TC 1093, isolated from a soil sample.
Last Modified6 March 2014
DownloadsMolfile
FormulaC33H38N6O10
Net Charge0
Average Mass678.699
Monoisotopic Mass678.26494
SMILESC/C=C\NC(=O)[C@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)C(=O)[C@H](C)CC)Cc2ccc(O)c(c2)-c2cccc3c2NC(=O)[C@@]3(O)[C@H]1O
InChIInChI=1S/C33H38N6O10/c1-4-11-35-30(46)25-27(43)33(49)19-8-6-7-17(24(19)39-32(33)48)18-12-16(9-10-22(18)40)13-20(37-31(47)26(42)15(3)5-2)28(44)36-21(14-23(34)41)29(45)38-25/h4,6-12,15,20-21,25,27,40,43,49H,5,13-14H2,1-3H3,(H2,34,41)(H,35,46)(H,36,44)(H,37,47)(H,38,45)(H,39,48)/b11-4-/t15-,20+,21+,25+,27+,33+/m1/s1
InChIKeyZIAXNZCTODBCKW-WYRJOJSMSA-N
Species of MetaboliteComponentSourceComments
Apiospora montagnei (ncbitaxon:255776) - PubMed (10814045) Strain: TC 1093
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
proteasome inhibitor  A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
ChEBI Ontology
Outgoing Relation(s)
TMC-95D (CHEBI:66248) has role antimicrobial agent (CHEBI:33281)
TMC-95D (CHEBI:66248) has role antineoplastic agent (CHEBI:35610)
TMC-95D (CHEBI:66248) has role fungal metabolite (CHEBI:76946)
TMC-95D (CHEBI:66248) has role proteasome inhibitor (CHEBI:52726)
TMC-95D (CHEBI:66248) is a indoles (CHEBI:24828)
TMC-95D (CHEBI:66248) is a lactam (CHEBI:24995)
TMC-95D (CHEBI:66248) is a macrocycle (CHEBI:51026)
TMC-95D (CHEBI:66248) is a phenols (CHEBI:33853)
TMC-95D (CHEBI:66248) is a secondary alcohol (CHEBI:35681)
TMC-95D (CHEBI:66248) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
(10S,11S,12S,15S,18S)-15-(2-amino-2-oxoethyl)-10,11,23-trihydroxy-18-{[(3R)-3-methyl-2-oxopentanoyl]amino}-9,14,17-trioxo-N-[(1Z)-prop-1-en-1-yl]-8,13,16-triazatetracyclo[18.3.1.02,7.06,10]tetracosa-1(24),2,4,6,20,22-hexaene-12-carboxamide
Citations