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CHEBI:66341 - UK-3A

ChEBI IDCHEBI:66341
ChEBI NameUK-3A
Stars
DefinitionA 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.
Last Modified6 March 2014
DownloadsMolfile
FormulaC25H28N2O8
Net Charge0
Average Mass484.505
Monoisotopic Mass484.18457
SMILESCC(C)C(=O)O[C@H]1[C@H](C)OC(=O)[C@@H](NC(=O)c2ncccc2O)COC(=O)[C@@H]1Cc1ccccc1
InChIInChI=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
InChIKeyLATFDMCUVSRKNK-DKXUYOFUSA-N
Species of MetaboliteComponentSourceComments
Streptomyces sp. (ncbitaxon:1931) mycelium (BTO:0001436) PubMed (9711246) Strain: 517-02
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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-methylpropanoateIUPAC
Registry NumbersSources
Reaxys:8124360Reaxys
Citations