CHEBI:18157 - aerobactin

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ChEBI Name aerobactin
ChEBI ID CHEBI:18157
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:13745, CHEBI:2499
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Formula C22H36N4O13
Net Charge 0
Average Mass 564.54040
Monoisotopic Mass 564.22789
InChI InChI=1S/C22H36N4O13/c1-13(27)25(38)9-5-3-7-15(19(31)32)23-17(29)11-22(37,21(35)36)12-18(30)24-16(20(33)34)8-4-6-10-26(39)14(2)28/h15-16,37-39H,3-12H2,1-2H3,(H,23,29)(H,24,30)(H,31,32)(H,33,34)(H,35,36)/t15-,16-/m0/s1
InChIKey KDHHWXGBNUCREU-HOTGVXAUSA-N
SMILES CC(=O)N(O)CCCC[C@H](NC(=O)CC(O)(CC(=O)N[C@@H](CCCCN(O)C(C)=O)C(O)=O)C(O)=O)C(O)=O
Metabolite of Species Details
Escherichia coli (NCBI:txid562) 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.
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.
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
virulence factor
Any toxin secreted by bacteria, viruses, fungi or protozoa enabling them to achieve colonisation of a niche in the host, inhibit or evade the host's immune response, enter and exit cells, or obtain nutrition from the host.
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ChEBI Ontology
Outgoing aerobactin (CHEBI:18157) has role Escherichia coli metabolite (CHEBI:76971)
aerobactin (CHEBI:18157) has role siderophore (CHEBI:26672)
aerobactin (CHEBI:18157) has role virulence factor (CHEBI:72316)
aerobactin (CHEBI:18157) is a L-lysine derivative (CHEBI:25095)
aerobactin (CHEBI:18157) is conjugate acid of aerobactinate(3−) (CHEBI:58396)
Incoming aerobactinate(3−) (CHEBI:58396) is conjugate base of aerobactin (CHEBI:18157)
IUPAC Name
N2,N2'-(3-carboxy-3-hydroxypentanedioyl)bis(N6-acetyl-N6-hydroxy-L-lysine)
Synonyms Sources
(8S,16S)-3,12,21-trihydroxy-2,10,14,22-tetraoxo-3,9,15,21-tetraazatricosane-8,12,16-tricarboxylic acid ChEBI
Aerobactin KEGG COMPOUND
Manual Xrefs Databases
Aerobactin Wikipedia
AEROBACTIN MetaCyc
C05554 KEGG COMPOUND
FDB023292 FooDB
HMDB0004051 HMDB
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Registry Number Type Source
26198-65-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17600077 PubMed citation Europe PMC
22716772 PubMed citation Europe PMC
23460907 PubMed citation Europe PMC
24664504 PubMed citation Europe PMC
26056379 PubMed citation Europe PMC
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28736222 PubMed citation Europe PMC
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29991301 PubMed citation Europe PMC
31032610 PubMed citation Europe PMC
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Last Modified
25 September 2020