Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 03:15:01 UTC
Update Date2025-10-07 16:05:51 UTC
Metabolite IDMMDBc0011360
Metabolite Identification
Common NameAmicoumacin B
DescriptionAmicoumacin B is a member of the amicoumacin chemical class, which consists of metabolites produced by certain actinomycetes. This compound has garnered attention for its antimicrobial properties, as evidenced by its minimum inhibitory concentration (MIC) of 10 µg/mL against various pathogens, including Liberibacter spp. (PMID:40742104 ). In ex vivo citrus hairy root assays, amicoumacin B significantly reduced populations of Candidatus Liberibacter asiaticus, highlighting its potential utility in agricultural applications (PMID:40742104 ). The compound was isolated from the culture broth of a Bacillus safensis strain, native to citrus environments, further underscoring its ecological relevance (PMID:40742104 ). Additionally, amicoumacin B has been implicated in the synthesis of derivatives through complex chemical processes, such as the formation of a 1,3-oxazinane ring (PMID:33817482 ). Its anti-quorum sensing (QS) activity has also been documented, contributing to its classification alongside other known amicoumacins (PMID:32640925 ). Moreover, a novel actinomycete producing amicoumacin B was identified from soil samples in Jinan, China, indicating its diverse sources and potential applications in biotechnology and medicine (PMID:19196788 ).
Structure
Synonyms
ValueSource
2-[(3S)-3-{[(2S)-4-amino-5-carboxy-1,2,3-trihydroxypentylidene]amino}-2-hydroxy-5-methylhexyl]-6-hydroxybenzoateGenerator
Molecular FormulaC20H30N2O9
Average Mass442.465
Monoisotopic Mass442.195130554
IUPAC Name2-[(3S)-3-{[(2S)-4-amino-5-carboxy-1,2,3-trihydroxypentylidene]amino}-2-hydroxy-5-methylhexyl]-6-hydroxybenzoic acid
Traditional Name2-[(3S)-3-{[(2S)-4-amino-5-carboxy-1,2,3-trihydroxypentylidene]amino}-2-hydroxy-5-methylhexyl]-6-hydroxybenzoic acid
CAS Registry NumberNot Available
SMILES
[H]C(N)(CC(O)=O)C([H])(O)[C@]([H])(O)C(O)=N[C@@]([H])(CC(C)C)C([H])(O)CC1=C(C(O)=O)C(O)=CC=C1
InChI Identifier
InChI=1S/C20H30N2O9/c1-9(2)6-12(22-19(29)18(28)17(27)11(21)8-15(25)26)14(24)7-10-4-3-5-13(23)16(10)20(30)31/h3-5,9,11-12,14,17-18,23-24,27-28H,6-8,21H2,1-2H3,(H,22,29)(H,25,26)(H,30,31)/t11?,12-,14?,17?,18-/m0/s1
InChI KeyZVMJOYORHWNPCZ-MLXNOORUSA-N