CHEBI:5019 - ferrichrome

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ChEBI Name ferrichrome
ChEBI ID CHEBI:5019
Definition A member of the class of ferrichromes that is an iron(III) chelate of a homodetic cyclic peptide made up of a tripeptide of glycine and a tripeptide of N4-acetyl-N4-hydroxy-L-ornithine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C27H42FeN9O12
Net Charge 0
Average Mass 740.52000
Monoisotopic Mass 740.230
InChI InChI=1S/C27H42N9O12.Fe/c1-16(37)34(46)10-4-7-19-25(43)30-14-23(41)28-13-22(40)29-15-24(42)31-20(8-5-11-35(47)17(2)38)26(44)33-21(27(45)32-19)9-6-12-36(48)18(3)39;/h19-21H,4-15H2,1-3H3,(H,28,41)(H,29,40)(H,30,43)(H,31,42)(H,32,45)(H,33,44);/q-3;+3/t19-,20-,21-;/m0./s1
InChIKey GGUNGDGGXMHBMJ-OCIDDWSYSA-N
SMILES [H][C@]12CCCN3O[Fe-3]456(ON(CCC[C@]([H])(NC(=O)CNC(=O)CNC(=O)CNC1=O)C(=O)N[C@@]([H])(CCCN(O4)C(C)=[O+]5)C(=O)N2)C(C)=[O+]6)[O+]=C3C
Metabolite of Species Details
Escherichia coli (NCBI:txid562) 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): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
(via iron(III) hydroxamate )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ferrichrome (CHEBI:5019) has role Escherichia coli metabolite (CHEBI:76971)
ferrichrome (CHEBI:5019) is a ferrichromes (CHEBI:61414)
IUPAC Name
(cyclo{glycyl-N5-(hydroxy-κO)-N5-[1-(oxo-κO)ethyl]-L-ornithyl-N5-(hydroxy-κO)-N5-[1-(oxo-κO)ethyl]-L-ornithyl-N5-(hydroxy-κO)-N5-[1-(oxo-κO)ethyl]-L-ornithylglycylglycyl})iron
Synonym Source
Ferrichrome KEGG COMPOUND
Manual Xrefs Databases
C00019283 KNApSAcK
C06228 KEGG COMPOUND
CPD0-2241 MetaCyc
View more database links
Registry Numbers Types Sources
14617047 Reaxys Registry Number Reaxys
15630-64-5 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
14269299 PubMed citation Europe PMC
Last Modified
25 January 2016
General Comment
2011-02-21 Ferrichromes are growth-promoting iron chelates that were first isolated from Ustilago sphaerogena (the rust fungus) in the 1950s. Ferrichrome itself and related compounds were subsequently isolated from Aspergillaceae and Penicillium resticulosum.