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CHEBI:84582 - schizokinen

ChEBI IDCHEBI:84582
ChEBI Nameschizokinen
Stars
DefinitionA hydroxamic acid resulting from the formal condensation of the primary amino group of N-(3-aminopropyl)-N-hydroxyacetamide (2 mol eq.) with the carboxy groups at positions 1 and 3 of citric acid. It is a siderophore produced by Bacillus megaterium and Anabaena species.
Last Modified30 January 2015
SubmitterGareth Owen
DownloadsMolfile
FormulaC16H28N4O9
Net Charge0
Average Mass420.419
Monoisotopic Mass420.18563
SMILESCC(=O)N(O)CCCNC(=O)CC(O)(CC(=O)NCCCN(O)C(C)=O)C(=O)O
InChIInChI=1S/C16H28N4O9/c1-11(21)19(28)7-3-5-17-13(23)9-16(27,15(25)26)10-14(24)18-6-4-8-20(29)12(2)22/h27-29H,3-10H2,1-2H3,(H,17,23)(H,18,24)(H,25,26)
InChIKeyYILWWVUXGMGOAM-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Bacillus megaterium (ncbitaxon:1404) - PubMed (4960152) Strain: ATCC 19213
Anabaena sp. (ncbitaxon:1167) - PubMed (6806241) Strain: ATCC 27898
Roles Classification
Chemical Roles:
siderophore  Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
siderophore  Any of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
ChEBI Ontology
Outgoing Relation(s)
schizokinen (CHEBI:84582) has functional parent citric acid (CHEBI:30769)
schizokinen (CHEBI:84582) has role bacterial metabolite (CHEBI:76969)
schizokinen (CHEBI:84582) has role siderophore (CHEBI:26672)
schizokinen (CHEBI:84582) is a 2-hydroxy carboxylic acid (CHEBI:52618)
schizokinen (CHEBI:84582) is a hydroxamic acid (CHEBI:24650)
IUPAC Name 
4-({3-[acetyl(hydroxy)amino]propyl}amino)-2-[2-({3-[acetyl(hydroxy)amino]propyl}amino)-2-oxoethyl]-2-hydroxy-4-oxobutanoic acid
Registry NumbersSources
Reaxys:2492423Reaxys
CAS:35418-52-1ChemIDplus
Citations