cystothiazole A (CHEBI:65716)

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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

Average Mass

422.56100

Monoisotopic Mass

422.13340

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.

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

Registry Number	Type	Source
8161374	Reaxys Registry Number	Reaxys

Last Modified

11 March 2015