CHEBI:156531 - ficellomycin

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This entity has been annotated by a third party. If you would like more information added to this entry, please contact ChEBI via email or GitHub.
ChEBI Name ficellomycin
ChEBI ID CHEBI:156531
Definition A dipeptide antibiotic containing an azabicyclohexane ring system that exhibits potent in vitro activity against Penicillium oxalicum and Staphylococcus aureus. It inhibits semi-conservative DNA replication by causing accumulation of 34S DNA species.
Stars This entity has been manually annotated by a third party.
Submitter Martin Larralde
Supplier Information ZINC000096095058
Download Molfile XML SDF
Formula C13H24N6O3
Net Charge 0
Average Mass 312.374
Monoisotopic Mass 312.19099
InChI InChI=1S/C13H24N6O3/c1-5(2)9(14)11(20)18-10(12(21)22)7-3-6(17-13(15)16)8-4-19(7)8/h5-10H,3-4,14H2,1-2H3,(H,18,20)(H,21,22)(H4,15,16,17)
InChIKey DGIHWRUPUISVIZ-UHFFFAOYSA-N
SMILES CC(C)C(C(=O)NC(C1CC(C2N1C2)NC(N)=N)C(=O)O)N
Metabolite of Species Details
Streptomyces ficellus (NCBI:txid1977088) of strain NRRL8067 See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ficellomycin (CHEBI:156531) has part L-valine (CHEBI:16414)
ficellomycin (CHEBI:156531) has part guanidino group (CHEBI:48551)
ficellomycin (CHEBI:156531) has role antibacterial agent (CHEBI:33282)
ficellomycin (CHEBI:156531) has role bacterial metabolite (CHEBI:76969)
ficellomycin (CHEBI:156531) has role DNA synthesis inhibitor (CHEBI:59517)
ficellomycin (CHEBI:156531) is a alkaloid (CHEBI:22315)
ficellomycin (CHEBI:156531) is a aziridines (CHEBI:22681)
ficellomycin (CHEBI:156531) is a dipeptide (CHEBI:46761)
ficellomycin (CHEBI:156531) is a pyrrolidines (CHEBI:38260)
Citations
Yue R, Li M, Wang Y, Guan Y, Zhang J, Yan Z, Liu F, Lu F, Zhang H (2020)
Insight into enzyme-catalyzed aziridine formation mechanism in ficellomycin biosynthesis.
European journal of medicinal chemistry 204, 112639 (Source: SUBMITTER) [PubMed:32712437]
[show Abstract]
Kurosawa S, Matsuda K, Hasebe F, Shiraishi T, Shin-Ya K, Kuzuyama T, Nishiyama M (2020)
Guanidyl modification of the 1-azabicyclo[3.1.0]hexane ring in ficellomycin essential for its biological activity.
Organic & biomolecular chemistry 18, 5137-5144 (Source: SUBMITTER) [PubMed:32582897]
[show Abstract]
He X, Li M, Song S, Wu X, Zhang J, Wu G, Yue R, Cui H, Song S, Ma C, Lu F, Zhang H (2018)
Ficellomycin: an aziridine alkaloid antibiotic with potential therapeutic capacity.
Applied microbiology and biotechnology 102, 4345-4354 (Source: SUBMITTER) [PubMed:29602982]
[show Abstract]
Liu Y, Li M, Mu H, Song S, Zhang Y, Chen K, He X, Wang H, Dai Y, Lu F, Yan Z, Zhang H (2017)
Identification and characterization of the ficellomycin biosynthesis gene cluster from Streptomyces ficellus.
Applied microbiology and biotechnology 101, 7589-7602 (Source: SUBMITTER) [PubMed:28894917]
[show Abstract]
Foulke-Abel J, Agbo H, Zhang H, Mori S, Watanabe CM (2011)
Mode of action and biosynthesis of the azabicycle-containing natural products azinomycin and ficellomycin.
Natural product reports 28, 693-704 (Source: SUBMITTER) [PubMed:21327255]
[show Abstract]
Kuo MS, Yurek DA, Mizsak SA (1989)
Structure elucidation of ficellomycin.
The Journal of antibiotics 42, 357-360 (Source: SUBMITTER) [PubMed:2708128]
[show Abstract]
Reusser F (1977)
Ficellomycin and feldamycin; inhibitors of bacterial semiconservative DNA replication.
Biochemistry 16, 3406-3412 (Source: SUBMITTER) [PubMed:329871]
[show Abstract]
Argoudelis AD, Reusser F, Whaley HA, Baczynskyj L, Mizsak SA, Wnuk RJ (1976)
Antibiotics produced by Streptomyces ficellus. I. Ficellomycin.
The Journal of antibiotics 29, 1001-1006 (Source: SUBMITTER) [PubMed:994319]
[show Abstract]