Ferric enterobactin (PAMDB001768)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001768
Identification
Name: Ferric enterobactin
Description:Ferric 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 Pseudomonas aeruginosa outer membrane protein FepA. (PMID 10998164) The Pseudomonas aeruginosa 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 Pseudomonas aeruginosa 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 Pseudomonas aeruginosa, 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 Pseudomonas aeruginosa outer membrane receptor protein for the siderophore ferric enterobactin. (PMID 7504275) FepA is the Pseudomonas aeruginosa outer membrane receptor for ferric enterobactin, colicin D and colicin B. (PMID 11532122)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 731.439
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.
Kingdom Organic compounds
Super ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct Parent Catechols
Alternative Parents
Substituents
  • 1,2-diphenol
  • Polyol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Organic transition metal salt
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors Not 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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity162.87 m3·mol-1ChemAxon
Polarizability65.12 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Adenosine triphosphate + Water + Ferric enterobactin > ADP + Ferric enterobactin + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Ferric enterobactin > ADP + Ferric enterobactin + Hydrogen ion + Phosphate
Ferric enterobactin + 3 Water >3 2,3-Dihydroxybenzoylserine + Fe3+ +3 Hydrogen ion
Enterochelin + Fe3+ > Ferric enterobactin
Ferric enterobactin + Water > ferric 2,3-dihydroxybenzoylserine
-->-->Ferric enterobactin + Adenosine triphosphate + Water Ferric enterobactin + Adenosine diphosphate + Hydrogen ion + ADP
Ferric enterobactin + Adenosine triphosphate + Water Ferric enterobactin + Adenosine diphosphate + Hydrogen ion + ADP
Pathways:
  • Biosynthesis of siderophore group nonribosomal peptides pae01053
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

Protein Details
• Ferric enterobactin transport ATP-binding protein fepC
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
Locus Tag:
PA4158
Molecular weight:
28.6 kDa
Protein Details
• Ferric enterobactin transport system permease protein fepD
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
Locus Tag:
PA4160
Molecular weight:
34.6 kDa
Protein Details
• Ferric enterobactin transport system permease protein fepG
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
Locus Tag:
PA4161
Molecular weight:
34.8 kDa
Protein Details
• Ferrienterobactin-binding periplasmic protein
General function:
Involved in binding
Specific function:
Binds ferrienterobactin; part of the binding-protein- dependent transport system for uptake of ferrienterobactin
Gene Name:
fepB
Locus Tag:
PA4159
Molecular weight:
32.1 kDa

Transporters

Protein Details
• Ferric enterobactin transport ATP-binding protein fepC
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
Locus Tag:
PA4158
Molecular weight:
28.6 kDa
Protein Details
• Ferric enterobactin transport system permease protein fepD
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
Locus Tag:
PA4160
Molecular weight:
34.6 kDa
Protein Details
• Ferric enterobactin transport system permease protein fepG
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
Locus Tag:
PA4161
Molecular weight:
34.8 kDa
Protein Details
• Ferrienterobactin-binding periplasmic protein
General function:
Involved in binding
Specific function:
Binds ferrienterobactin; part of the binding-protein- dependent transport system for uptake of ferrienterobactin
Gene Name:
fepB
Locus Tag:
PA4159
Molecular weight:
32.1 kDa
Protein Details
• Ferrienterobactin receptor
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 Pseudomonas aeruginosa to extract iron from the environment. FepA also acts as a receptor for colicins B and D
Gene Name:
fepA
Locus Tag:
PA2688
Molecular weight:
81 kDa