ferrienterobactin(3-) (CHEBI:28199)

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CHEBI:28199 - ferrienterobactin(3−)

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ChEBI Name	ferrienterobactin(3−)

ChEBI ID	CHEBI:28199

ChEBI ASCII Name	ferrienterobactin(3-)

Definition	Iron (Fe3+) siderophore

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

Submitter	Sandra Orchard

Secondary ChEBI IDs	CHEBI:21133, CHEBI:144426, CHEBI:4993

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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1.5432 3.5118 -1.4068 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1092 1.4465 -0.7859 O 0 0 0 0 0 0 0 0 0 0 0 0

3.3542 4.7668 -0.3881 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2842 4.6999 -1.2963 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5554 3.4026 -2.1834 O 0 0 0 0 0 0 0 0 0 0 0 0

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-0.0037 -1.9650 -3.1458 C 0 0 0 0 0 0 0 0 0 0 0 0

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-2.2633 0.9405 -2.6209 C 0 0 0 0 0 0 0 0 0 0 0 0

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-1.9297 -1.3363 1.4129 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.5595 0.9667 1.7800 C 0 0 0 0 0 0 0 0 0 0 0 0

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M CHG 1 48 -3

M END): 24 ms

reading 70 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

70 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Formula

C30H21FeN3O15

Net Charge

-3

Average Mass

719.351

Monoisotopic Mass

719.03385

InChI

InChI=1S/C30H27N3O15.Fe/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38;/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42);/q;+3/p-6/t16-,17-,18-;/m0./s1

InChIKey

NGILTSZTOFYVBF-UVJOBNTFSA-H

SMILES

[H][C@]12COC(=O)[C@]3([H])COC(=O)[C@]([H])(COC1=O)NC(=O)C1=C4O[Fe-3]56(OC7=CC=CC(=C7O5)C(=O)N2)(OC4=CC=C1)OC1=CC=CC(=C1O6)C(=O)N3

Metabolite of Species	Details
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	ferrienterobactin(3−) (CHEBI:28199) has part enterobactin(6−) (CHEBI:38150) ferrienterobactin(3−) (CHEBI:28199) has role Escherichia coli metabolite (CHEBI:76971) ferrienterobactin(3−) (CHEBI:28199) is a Fe(III)-complexed siderophore (CHEBI:84734) ferrienterobactin(3−) (CHEBI:28199) is a organic anion (CHEBI:25696) ferrienterobactin(3−) (CHEBI:28199) is conjugate base of ferrienterobactin (CHEBI:38151)

Incoming	ferrienterobactin (CHEBI:38151) is conjugate acid of ferrienterobactin(3−) (CHEBI:28199)

IUPAC Names

{N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-di(hydroxy-κO)benzamidato](6−)}ferrate(3−)

{N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-di(hydroxy-κO)benzamidato]}ferrate(3−)

Synonyms	Sources
[Fe(ent)]³⁻	ChEBI
Fe(III)-enterobactin	UniProt
Fe-enterobactin	KEGG COMPOUND
FeEnt	ChEBI
ferric enterobactin	ChEBI
ferric-enterobactin	ChEBI
ferrienterobactin	ChemIDplus
ferrienterochelin	ChemIDplus

Manual Xrefs	Databases
C06230	KEGG COMPOUND
FERRIC-ENTEROBACTIN-COMPLEX	MetaCyc
View more database links

Registry Numbers	Types	Sources
2494246	Gmelin Registry Number	Gmelin
61481-53-6	CAS Registry Number	ChemIDplus
885856	Gmelin Registry Number	Gmelin

Citations	Types	Sources
12655062	PubMed citation	Europe PMC
16819888	PubMed citation	Europe PMC
21842211	PubMed citation	Europe PMC
23905838	PubMed citation	Europe PMC
24981231	PubMed citation	Europe PMC
28956921	PubMed citation	Europe PMC
30135989	PubMed citation	Europe PMC
31413254	PubMed citation	Europe PMC
32098871	PubMed citation	Europe PMC
9852016	PubMed citation	Europe PMC

Last Modified

12 July 2022

CHEBI:28199 - ferrienterobactin(3−)

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