schizokinen (CHEBI:84582)

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ChEBI Name	schizokinen

ChEBI ID	CHEBI:84582

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C16H28N4O9

Net Charge

Average Mass

420.41490

Monoisotopic Mass

420.18563

InChI

InChI=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)

InChIKey

YILWWVUXGMGOAM-UHFFFAOYSA-N

SMILES

CC(=O)N(O)CCCNC(=O)CC(O)(CC(=O)NCCCN(O)C(C)=O)C(O)=O

Metabolite of Species	Details
Anabaena sp. (NCBI:txid1167)	of strain ATCC 27898 See: PubMed
Bacillus megaterium (NCBI:txid1404)	of strain ATCC 19213 See: PubMed

Roles Classification
Chemical Role(s):	siderophore Any of low-molecular-mass iron(3)-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 (Bronsted base). (via oxoacid )

Biological Role(s):	siderophore Any of low-molecular-mass iron(3)-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	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

Last Modified

30 January 2015