Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 06:47:20 UTC
Update Date2025-10-07 16:06:30 UTC
Metabolite IDMMDBc0016064
Metabolite Identification
Common NameBacilysin
DescriptionBacilysin is a lipopeptide antibiotic belonging to the chemical class of cyclic peptides. Its chemical structure features a cyclic arrangement of amino acids, which contributes to its antimicrobial properties. Bacilysin is synthesized through a biosynthetic pathway involving gene clusters that encode for various enzymes responsible for the assembly of its peptide backbone and modification steps. Genomic analyses have identified bacilysin biosynthesis clusters in several Bacillus species, including Bacillus velezensis, which also produce other secondary metabolites such as surfactin and fengycin (PMID:40964052 ). Furthermore, studies have highlighted the presence of bacilysin among diverse secondary metabolite biosynthetic gene clusters, indicating its role in the complex metabolic networks of these bacteria (PMID:40941136 ). Liquid chromatography time of flight mass spectrometry (LC-TOF/MS) has confirmed the detection of bacilysin alongside other lipopeptides, showcasing its co-production with other antimicrobial compounds (PMID:40782405 ). The identification of bacilysin gene clusters in various strains underscores its significance in microbial ecology and potential applications in biocontrol (PMID:40767861 ). Additionally, bacilysin's antimicrobial properties are further supported by genome prediction analyses that reveal its biosynthetic potential (PMID:40718143 ).
Structure
Synonyms
ValueSource
Ala-(2,3-epoxycyclohexanone-4)-alaMeSH
BacillinMeSH
TetaineMeSH
Molecular FormulaC12H18N2O5
Average Mass270.285
Monoisotopic Mass270.121571688
IUPAC Name2-[(2-amino-1-hydroxypropylidene)amino]-3-[(1R,2R,6R)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid
Traditional Name2-[(2-amino-1-hydroxypropylidene)amino]-3-[(1R,2R,6R)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid
CAS Registry NumberNot Available
SMILES
[H]C(C)(N)C(O)=NC([H])(C[C@@]1([H])CCC(=O)[C@]2([H])O[C@]12[H])C(O)=O
InChI Identifier
InChI=1S/C12H18N2O5/c1-5(13)11(16)14-7(12(17)18)4-6-2-3-8(15)10-9(6)19-10/h5-7,9-10H,2-4,13H2,1H3,(H,14,16)(H,17,18)/t5?,6-,7?,9-,10+/m1/s1
InChI KeyXFOUAXMJRHNTOP-PCPUDTNWSA-N