Record Information
Version2.0
Creation Date2012-07-30 14:55:30 -0600
Update Date2015-06-03 17:21:15 -0600
Secondary Accession Numbers
  • ECMDB21372
Identification
Name:Ferric enterobactin
DescriptionFerric enterobactin is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. Ferric enterobactin is a catecholate siderophore that binds with high affinity (Kd approximately 10-10 M) to the Escherichia coli outer membrane protein FepA. (PMID 10998164) The Escherichia coli FepA protein is an energy- and TonB-dependent, ligand-binding porin that functions as a receptor for the siderophore ferric enterobactin and colicins B and D. (PMID 9268330) The periplasmic protein FepB of Escherichia coli is a component of the ferric enterobactin transport system. (PMID 10986237) The ferric enterobactin receptor, FepA, is a TonB-dependent gated porin that transports the siderophore ferric enterobactin across the outer membrane of gram-negative bacteria. (PMID 7947735) In Escherichia coli, the outer membrane protein FepA is a receptor for the siderophore complex ferric enterobactin and for colicins B and D. (PMID 2201687) FepA is an Escherichia coli outer membrane receptor protein for the siderophore ferric enterobactin. (PMID 7504275) FepA is the Escherichia coli outer membrane receptor for ferric enterobactin, colicin D and colicin B. (PMID 11532122)
Structure
Thumb
Synonyms:
  • Fe-enterobactin
  • Fe-enterochlin
  • Ferric enterobactin complex
  • [Fe(ent)]3
  • {N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-di(hydroxy-kappaO)benzamidato]}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-kappao)benzamidato]}ferric acid(3)
Chemical Formula:C30H33FeN3O15
Weight:Average: 731.439
Monoisotopic: 731.126109534
InChI Key:WPYKFMKTUGWUGY-UHFFFAOYSA-N
InChI:InChI=1S/C30H33N3O15.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;/h1-9,16-18,28-30,34-39,43-45H,10-12H2,(H,31,40)(H,32,41)(H,33,42);
CAS number:Not Available
IUPAC Name:N-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trihydroxy-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzene-1-carboximidic acid iron
Traditional IUPAC Name:N-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trihydroxy-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid iron
SMILES:[Fe].OC1OCC(N=C(O)C2=C(O)C(O)=CC=C2)C(O)OCC(N=C(O)C2=C(O)C(O)=CC=C2)C(O)OCC1N=C(O)C1=C(O)C(O)=CC=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylamides
Alternative Parents
Substituents
  • Salicylamide
  • Benzamide
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organic transition metal salt
  • Organic salt
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
logP4.16ChemAxon
pKa (Strongest Acidic)6.54ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area307.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity162.87 m³·mol⁻¹ChemAxon
Polarizability65.12 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
Biosynthesis of siderophore group nonribosomal peptidesPW000760 ThumbThumb?image type=greyscaleThumb?image type=simple
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Biosynthesis of siderophore group nonribosomal peptides ec01053
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-28c8afcd3b5f368a80dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-28c8afcd3b5f368a80dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0000000900-28c8afcd3b5f368a80dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-2588cf04e699537c7c41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000000900-2588cf04e699537c7c41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0000000900-2588cf04e699537c7c41View in MoNA
References
References:
  • Barnard, T. J., Watson, M. E. Jr, McIntosh, M. A. (2001). "Mutations in the Escherichia coli receptor FepA reveal residues involved in ligand binding and transport." Mol Microbiol 41:527-536. Pubmed: 11532122
  • Cao, Z., Qi, Z., Sprencel, C., Newton, S. M., Klebba, P. E. (2000). "Aromatic components of two ferric enterobactin binding sites in Escherichia coli FepA." Mol Microbiol 37:1306-1317. Pubmed: 10998164
  • Liu, J., Rutz, J. M., Feix, J. B., Klebba, P. E. (1993). "Permeability properties of a large gated channel within the ferric enterobactin receptor, FepA." Proc Natl Acad Sci U S A 90:10653-10657. Pubmed: 7504275
  • Liu, J., Rutz, J. M., Klebba, P. E., Feix, J. B. (1994). "A site-directed spin-labeling study of ligand-induced conformational change in the ferric enterobactin receptor, FepA." Biochemistry 33:13274-13283. Pubmed: 7947735
  • Payne, M. A., Igo, J. D., Cao, Z., Foster, S. B., Newton, S. M., Klebba, P. E. (1997). "Biphasic binding kinetics between FepA and its ligands." J Biol Chem 272:21950-21955. Pubmed: 9268330
  • Sprencel, C., Cao, Z., Qi, Z., Scott, D. C., Montague, M. A., Ivanoff, N., Xu, J., Raymond, K. M., Newton, S. M., Klebba, P. E. (2000). "Binding of ferric enterobactin by the Escherichia coli periplasmic protein FepB." J Bacteriol 182:5359-5364. Pubmed: 10986237
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID440956
Kegg IDC06230
ChemSpider ID389783
Wikipedia IDNot Available
BioCyc IDFERRIC-ENTEROBACTIN-COMPLEX
EcoCyc IDFERRIC-ENTEROBACTIN-COMPLEX

Enzymes

General function:
Involved in iron ion binding
Specific function:
Upon internalization, ferric enterobactin is processed via an exquisitely specific pathway that is dependent on FES activity, making iron available for metabolic use
Gene Name:
fes
Uniprot ID:
P13039
Molecular weight:
42569
General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for ferric enterobactin. Probably responsible for energy coupling to the transport system
Gene Name:
fepC
Uniprot ID:
P23878
Molecular weight:
29784
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for ferric enterobactin. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
fepD
Uniprot ID:
P23876
Molecular weight:
33871
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for ferric enterobactin. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
fepG
Uniprot ID:
P23877
Molecular weight:
34910
General function:
Involved in binding
Specific function:
Binds ferrienterobactin; part of the binding-protein- dependent transport system for uptake of ferrienterobactin
Gene Name:
fepB
Uniprot ID:
P0AEL6
Molecular weight:
34283

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for ferric enterobactin. Probably responsible for energy coupling to the transport system
Gene Name:
fepC
Uniprot ID:
P23878
Molecular weight:
29784
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for ferric enterobactin. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
fepD
Uniprot ID:
P23876
Molecular weight:
33871
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for ferric enterobactin. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
fepG
Uniprot ID:
P23877
Molecular weight:
34910
General function:
Involved in binding
Specific function:
Binds ferrienterobactin; part of the binding-protein- dependent transport system for uptake of ferrienterobactin
Gene Name:
fepB
Uniprot ID:
P0AEL6
Molecular weight:
34283
General function:
Involved in protein transporter activity
Specific function:
Involved in the tonB-dependent energy-dependent transport of various receptor-bound substrates. Protects exbD from proteolytic degradation and functionally stabilizes tonB
Gene Name:
exbB
Uniprot ID:
P0ABU7
Molecular weight:
26287
General function:
Involved in transporter activity
Specific function:
Involved in the tonB-dependent energy-dependent transport of various receptor-bound substrates
Gene Name:
exbD
Uniprot ID:
P0ABV2
Molecular weight:
15527
General function:
Involved in receptor activity
Specific function:
This protein is involved in the initial step of iron uptake by binding ferrienterobactin (Fe-ENT), an iron chelatin siderophore that allows E.coli to extract iron from the environment. FepA also acts as a receptor for colicins B and D
Gene Name:
fepA
Uniprot ID:
P05825
Molecular weight:
82106
General function:
Involved in iron ion transmembrane transporter activity
Specific function:
Interacts with outer membrane receptor proteins that carry out high-affinity binding and energy dependent uptake into the periplasmic space of specific substrates such as cobalamin, and various iron compounds (such as iron dicitrate, enterochelin, aerobactin, etc.). In the absence of tonB these receptors bind their substrates but do not carry out active transport. TonB also interacts with some colicins and is involved in the energy- dependent, irreversible steps of bacteriophages phi 80 and T1 infection. It could act to transduce energy from the cytoplasmic membrane to specific energy-requiring processes in the outer membrane, resulting in the release into the periplasm of ligands bound by these outer membrane proteins
Gene Name:
tonB
Uniprot ID:
P02929
Molecular weight:
26094