CHEBI:80056 - (+)-zwittermicin A

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ChEBI Name (+)-zwittermicin A
ChEBI ID CHEBI:80056
Definition The (+)-enantiomer of zwittermicin A. It is a water-soluble natural antibiotic from the fermentation of the soil-borne bacterium Bacillus cereus and shows significant activity against phytopathogenic fungi.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C13H28N6O8
Net Charge 0
Average Mass 396.401
Monoisotopic Mass 396.19686
InChI InChI=1S/C13H28N6O8/c14-4(3-20)6(21)1-7(22)8(15)9(23)10(24)12(26)19-5(11(16)25)2-18-13(17)27/h4-10,20-24H,1-3,14-15H2,(H2,16,25)(H,19,26)(H3,17,18,27)/t4-,5+,6+,7+,8+,9+,10-/m1/s1
InChIKey FYIPKJHNWFVEIR-FXQWNPMTSA-N
SMILES N[C@H](CO)[C@@H](O)C[C@H](O)[C@H](N)[C@H](O)[C@@H](O)C(=O)N[C@@H](CNC(N)=O)C(N)=O
Metabolite of Species Details
Bacillus cereus (NCBI:txid1396) 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): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via peptide antibiotic )
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ChEBI Ontology
Outgoing (+)-zwittermicin A (CHEBI:80056) has role antifungal agent (CHEBI:35718)
(+)-zwittermicin A (CHEBI:80056) has role bacterial metabolite (CHEBI:76969)
(+)-zwittermicin A (CHEBI:80056) is a 4,8-diamino-N-[1-amino-3-(carbamoylamino)-1-oxopropan-2-yl]-2,3,5,7,9-pentahydroxynonanamide (CHEBI:167622)
(+)-zwittermicin A (CHEBI:80056) is a peptide antibiotic (CHEBI:25903)
(+)-zwittermicin A (CHEBI:80056) is enantiomer of (−)-zwittermicin A (CHEBI:167210)
Incoming (−)-zwittermicin A (CHEBI:167210) is enantiomer of (+)-zwittermicin A (CHEBI:80056)
IUPAC Name
(2R,3S,4S,5S,7S,8R)-4,8-diamino-N-[(2S)-1-amino-3-(carbamoylamino)-1-oxopropan-2-yl]-2,3,5,7,9-pentahydroxynonanamide
Synonym Source
(+)-zwittermicin A ChEBI
Manual Xrefs Databases
C15726 KEGG COMPOUND
CPD-18237 MetaCyc
EP1163347 Patent
Zwittermicin_A Wikipedia
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Registry Number Type Source
155547-95-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10464220 PubMed citation Europe PMC
10521664 PubMed citation Europe PMC
14711631 PubMed citation Europe PMC
15281929 PubMed citation Europe PMC
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18798190 PubMed citation Europe PMC
19062654 PubMed citation Europe PMC
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31622586 PubMed citation Europe PMC
645857 Chinese Abstracts citation Europe PMC
8031096 PubMed citation Europe PMC
8763956 PubMed citation Europe PMC
Last Modified
22 April 2022
General Comment
2020-09-11 The structure of zwittermicin A updated due to evidence found in PMID:18798190.