CHEBI:66341 - UK-3A

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ChEBI Name UK-3A
Definition A lactone which is 9-methyl-1,5-dioxonane-2,6-dione substituted by a benzyl group at position 8, a [(3-hydroxy-pyridine-2-yl)carbonyl]amino group at position 3 and an isobutyryloxy group at position 7. It is isolated from the mycelia cake of Streptomyces sp. 517-02 and exhibits potent antifungal activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H28N2O8
Net Charge 0
Average Mass 484.49840
Monoisotopic Mass 484.18457
InChI InChI=1S/C25H28N2O8/c1-14(2)23(30)35-21-15(3)34-25(32)18(27-22(29)20-19(28)10-7-11-26-20)13-33-24(31)17(21)12-16-8-5-4-6-9-16/h4-11,14-15,17-18,21,28H,12-13H2,1-3H3,(H,27,29)/t15-,17+,18-,21-/m0/s1
SMILES CC(C)C(=O)O[C@H]1[C@H](C)OC(=O)[C@H](COC(=O)[C@@H]1Cc1ccccc1)NC(=O)c1ncccc1O
Metabolite of Species Details
Streptomyces sp. (NCBI:txid1931) Found in mycelium (BTO:0001436). of strain 517-02 See: PubMed
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing UK-3A (CHEBI:66341) has role antifungal agent (CHEBI:35718)
UK-3A (CHEBI:66341) has role antimicrobial agent (CHEBI:33281)
UK-3A (CHEBI:66341) has role bacterial metabolite (CHEBI:76969)
UK-3A (CHEBI:66341) is a aromatic amide (CHEBI:62733)
UK-3A (CHEBI:66341) is a lactone (CHEBI:25000)
UK-3A (CHEBI:66341) is a monocarboxylic acid amide (CHEBI:29347)
UK-3A (CHEBI:66341) is a monohydroxypyridine (CHEBI:38182)
Synonym Source
(3S,6S,7R,8R)-8-benzyl-3-{[(3-hydroxypyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate IUPAC
Registry Number Type Source
8124360 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20621723 PubMed citation Europe PMC
9510913 PubMed citation Europe PMC
9711246 PubMed citation Europe PMC
Last Modified
06 March 2014