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CHEBI:167048 - levesquamide

ChEBI IDCHEBI:167048
ChEBI Namelevesquamide
Stars
DefinitionA polyketide-nonribosomal peptide with an isothiazolinone moiety found in Streptomyces sp. RKND-216. It has a strong selective activity against M. tuberculosis, with no cytotoxicity against mammalian cell lines.
Last Modified27 April 2021
SubmitterMartin Larralde
DownloadsMolfile
FormulaC28H34N6O9S
Net Charge0
Average Mass630.680
Monoisotopic Mass630.21080
SMILESCOc1c(-c2coc(-c3ccccc3N)n2)nc2c(=O)n([C@@H](CO)C(=O)NC[C@@H](O)C(=O)N[C@H](CO)CC(C)C)sc2c1O
InChIInChI=1S/C28H34N6O9S/c1-13(2)8-14(10-35)31-26(40)19(37)9-30-25(39)18(11-36)34-28(41)21-24(44-34)22(38)23(42-3)20(33-21)17-12-43-27(32-17)15-6-4-5-7-16(15)29/h4-7,12-14,18-19,35-37H,8-11,29H2,1-3H3,(H,30,39)(H,31,40)(H,33,38)/t14-,18-,19+/m0/s1
InChIKeyDZVHAUSOBYTBDX-ZOCIIQOWSA-N
Species of MetaboliteComponentSourceComments
Streptomyces sp. RKND-216 (ncbitaxon:2562581) - PubMed (32363877)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
Application:
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
ChEBI Ontology
Outgoing Relation(s)
levesquamide (CHEBI:167048) has role antitubercular agent (CHEBI:33231)
levesquamide (CHEBI:167048) has role bacterial metabolite (CHEBI:76969)
levesquamide (CHEBI:167048) is a 1,3-oxazoles (CHEBI:46812)
levesquamide (CHEBI:167048) is a anilines (CHEBI:22562)
levesquamide (CHEBI:167048) is a aromatic ether (CHEBI:35618)
levesquamide (CHEBI:167048) is a polyketide (CHEBI:26188)
levesquamide (CHEBI:167048) is a primary alcohol (CHEBI:15734)
levesquamide (CHEBI:167048) is a secondary alcohol (CHEBI:35681)
levesquamide (CHEBI:167048) is a secondary carboxamide (CHEBI:140325)
levesquamide (CHEBI:167048) is a thiazolopyridine (CHEBI:46956)
IUPAC Name 
(2S)-2-{5-[2-(2-aminophenyl)-1,3-oxazol-4-yl]-7-hydroxy-6-methoxy-3-oxo[1,2]thiazolo[4,5-b]pyridin-2(3H)-yl}-3-hydroxy-N-[(2R)-2-hydroxy-3-{[(2S)-1-hydroxy-4-methylpentan-2-yl]amino}-3-oxopropyl]propanamide
Citations