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CHEBI:65716 - cystothiazole A

ChEBI IDCHEBI:65716
ChEBI Namecystothiazole A
Stars
DefinitionAn organonitrogen heterocyclic antibiotic that is 2,4'-bi-1,3-thiazole substituted by an isopropyl group at position 2' and a 3,5,7-trimethoxy-4-methyl-7-oxohepta-1,5-dien-1-yl group at position 4 (the 2E,4R,5S,6E stereoisomer). It is isolated from the culture broth of myxobacterium, Cystobacter fuscus, and exhibits antifungal and cytotoxic activity.
Last Modified11 March 2015
DownloadsMolfile
FormulaC20H26N2O4S2
Net Charge0
Average Mass422.572
Monoisotopic Mass422.13340
SMILESCOC(=O)/C=C(/OC)[C@H](C)[C@H](/C=C/c1csc(-c2csc(C(C)C)n2)n1)OC
InChIInChI=1S/C20H26N2O4S2/c1-12(2)19-22-15(11-28-19)20-21-14(10-27-20)7-8-16(24-4)13(3)17(25-5)9-18(23)26-6/h7-13,16H,1-6H3/b8-7+,17-9+/t13-,16+/m1/s1
InChIKeyLRTJMINIVSPVMX-ZVJWTWILSA-N
Species of MetaboliteComponentSourceComments
Cystobacter fuscus (ncbitaxon:43) - PubMed (9589062)
Roles Classification
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
cystothiazole A (CHEBI:65716) has role antifungal agent (CHEBI:35718)
cystothiazole A (CHEBI:65716) has role antineoplastic agent (CHEBI:35610)
cystothiazole A (CHEBI:65716) has role bacterial metabolite (CHEBI:76969)
cystothiazole A (CHEBI:65716) is a 1,3-thiazoles (CHEBI:38418)
cystothiazole A (CHEBI:65716) is a biaryl (CHEBI:64459)
cystothiazole A (CHEBI:65716) is a enoate ester (CHEBI:51702)
cystothiazole A (CHEBI:65716) is a enol ether (CHEBI:47985)
cystothiazole A (CHEBI:65716) is a methyl ester (CHEBI:25248)
cystothiazole A (CHEBI:65716) is a organonitrogen heterocyclic antibiotic (CHEBI:25558)
IUPAC Name 
methyl (2E,4R,5S,6E)-3,5-dimethoxy-4-methyl-7-[2'-(propan-2-yl)-2,4'-bi-1,3-thiazol-4-yl]hepta-2,6-dienoate
Synonyms  Source
melithiazole EChEBI
(+)-cystothiazole AChEBI
Cystothiazole AKEGG COMPOUND
Manual XrefsDatabases
C00016023KNApSAcK
C15712KEGG COMPOUND
Registry NumbersSources
Reaxys:8161374Reaxys
Citations