Ferric enterobactin (ECMDB21372) (M2MDB001768)
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| Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-07-30 14:55:30 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-06-03 17:21:15 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| 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 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 |  | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| 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. | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Benzenoids | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Benzene and substituted derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Benzoic acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Salicylamides | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents |
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| Substituents |
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| Molecular Framework | Aromatic heteromonocyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| 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 Adenosine triphosphate + Ferric enterobactin + Water > ADP + Phosphate + Ferric enterobactin + Hydrogen ion Adenosine triphosphate + Ferric enterobactin + Water > ADP + Phosphate + Ferric enterobactin + Hydrogen ion Ferric enterobactin + Adenosine triphosphate + Water Ferric enterobactin + Adenosine diphosphate + Hydrogen ion + ADP Ferric enterobactin + Adenosine triphosphate + Water Ferric enterobactin + Adenosine diphosphate + Hydrogen ion + ADP | |||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: |
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| EcoCyc Pathways: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||
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| References: |
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| Synthesis Reference: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||
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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