CHEBI:65716 - cystothiazole A

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ChEBI Name cystothiazole A
ChEBI ID CHEBI:65716
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H26N2O4S2
Net Charge 0
Average Mass 422.56100
Monoisotopic Mass 422.133
InChI InChI=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
InChIKey LRTJMINIVSPVMX-ZVJWTWILSA-N
SMILES CO[C@@H](\C=C\c1csc(n1)-c1csc(n1)C(C)C)[C@@H](C)C(\OC)=C/C(=O)OC
Metabolite of Species Details
Cystobacter fuscus (NCBI:txid43) See: PubMed
Roles Classification
Biological Role(s): 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.
(via heterocyclic antibiotic )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(+)-cystothiazole A ChEBI
Cystothiazole A KEGG COMPOUND
melithiazole E ChEBI
Manual Xrefs Databases
C00016023 KNApSAcK
C15712 KEGG COMPOUND
View more database links
Registry Number Type Source
8161374 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12817811 PubMed citation Europe PMC
14572275 PubMed citation Europe PMC
14981303 PubMed citation Europe PMC
17978521 PubMed citation Europe PMC
22621309 PubMed citation Europe PMC
9589062 PubMed citation Europe PMC
Last Modified
11 March 2015