Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 04:38:38 UTC
Update Date2025-10-07 16:06:07 UTC
Metabolite IDMMDBc0013313
Metabolite Identification
Common NameAmicoumacin A
DescriptionAmicoumacin A is a member of the class of natural products known as antibiotics, specifically a metabolite with significant antibacterial properties. This compound has been shown to exhibit a minimum inhibitory concentration (MIC) of 1.25 µg/mL against certain bacterial strains (PMID:40742104 ). Its presence in cell-free supernatants has been linked to bactericidal effects against Vibrio species (PMID:38573920 ), and it has been identified as a major antibacterial metabolite contributing to the antagonistic activity of specific bacterial strains (PMID:35163108 ). The biosynthetic gene cluster responsible for amicoumacin A has been elucidated through whole genome sequencing, highlighting its importance in microbial ecology (PMID:33193216 ). Mechanistically, amicoumacin A inhibits bacterial growth by targeting the ribosome and disrupting translation processes (PMID:33643246 ). Notably, it has demonstrated high activity against shrimp pathogens, indicating its potential application in aquaculture (PMID:33193216 ). Additionally, amicoumacin A serves as a precursor for the synthesis of related compounds, such as hetiamacins B-F, showcasing its versatility in chemical synthesis (PMID:33817482 ). Overall, amicoumacin A represents a promising candidate for further research in antibiotic development and microbial interactions.
Structure
Synonyms
ValueSource
Amicoumacin-aMeSH
Molecular FormulaC20H29N3O7
Average Mass423.466
Monoisotopic Mass423.200550286
IUPAC Name(2S,3S,4S)-4-amino-2,3-dihydroxy-N-[(1S)-1-[(3S)-8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]-3-methylbutyl]hexanediimidic acid
Traditional Name(2S,3S,4S)-4-amino-2,3-dihydroxy-N-[(1S)-1-[(3S)-8-hydroxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]-3-methylbutyl]hexanediimidic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(CC(O)=N)[C@]([H])(O)[C@]([H])(O)C(O)=N[C@@]([H])(CC(C)C)[C@]1([H])CC2=C(C(=O)O1)C(O)=CC=C2
InChI Identifier
InChI=1S/C20H29N3O7/c1-9(2)6-12(23-19(28)18(27)17(26)11(21)8-15(22)25)14-7-10-4-3-5-13(24)16(10)20(29)30-14/h3-5,9,11-12,14,17-18,24,26-27H,6-8,21H2,1-2H3,(H2,22,25)(H,23,28)/t11-,12-,14-,17-,18-/m0/s1
InChI KeyDCPWYLSPIAHJFU-YKRRISCLSA-N