CHEBI:66339 - UK-2A

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ChEBI Name UK-2A
ChEBI ID CHEBI:66339
Definition A lactone which is 9-methyl-1,5-dioxonane-2,6-dione substituted by a benzyl group at position 8, a [(3-hydroxy-4-methoxypyridine-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.
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Formula C26H30N2O9
Net Charge 0
Average Mass 514.52440
Monoisotopic Mass 514.19513
InChI InChI=1S/C26H30N2O9/c1-14(2)24(31)37-22-15(3)36-26(33)18(28-23(30)20-21(29)19(34-4)10-11-27-20)13-35-25(32)17(22)12-16-8-6-5-7-9-16/h5-11,14-15,17-18,22,29H,12-13H2,1-4H3,(H,28,30)/t15?,17?,18-,22-/m0/s1
InChIKey MLGCATYQZVMGBG-DRHHIBKESA-N
SMILES COc1ccnc(C(=O)N[C@H]2COC(=O)C(Cc3ccccc3)[C@@H](OC(=O)C(C)C)C(C)OC2=O)c1O
Metabolite of Species Details
Streptomyces sp. (NCBI:txid1931) Found in mycelium (BTO:0001436). of strain 517-02 See: PubMed
Roles Classification
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing UK-2A (CHEBI:66339) has role antifungal agent (CHEBI:35718)
UK-2A (CHEBI:66339) has role antimicrobial agent (CHEBI:33281)
UK-2A (CHEBI:66339) has role bacterial metabolite (CHEBI:76969)
UK-2A (CHEBI:66339) is a aromatic amide (CHEBI:62733)
UK-2A (CHEBI:66339) is a aromatic ether (CHEBI:35618)
UK-2A (CHEBI:66339) is a lactone (CHEBI:25000)
UK-2A (CHEBI:66339) is a monocarboxylic acid amide (CHEBI:29347)
UK-2A (CHEBI:66339) is a monohydroxypyridine (CHEBI:38182)
Synonym Source
(3S,7R)-8-benzyl-3-{[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate IUPAC
Registry Number Type Source
8124863 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10048572 PubMed citation Europe PMC
10580388 PubMed citation Europe PMC
11560380 PubMed citation Europe PMC
12760689 PubMed citation Europe PMC
8784423 PubMed citation Europe PMC
9031668 PubMed citation Europe PMC
Last Modified
06 March 2014