Record Information
Version2.0
Creation Date2012-07-30 14:55:20 -0600
Update Date2015-07-22 15:13:49 -0600
Secondary Accession Numbers
  • ECMDB21331
Identification
Name:ferric 2,3-dihydroxybenzoylserine
DescriptionFerric 2,3-dihydroxybenzoylserine belongs to the class of Hippuric Acid Derivatives. These are compounds containing an hippuric acid or a derivative, with a structure characterized the presence of a benzoyl group linked to the N-terminal of a glycine. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • Dihydroxybenzoylserine-iron
  • Ferric 2,3-dihydroxybenzoylserine
  • Ferric dihydroxybenzoylserine
  • Hydrolyzed ferric enterobactin complex
Chemical Formula:C10H11FeNO6
Weight:Average: 297.044
Monoisotopic: 296.993573
InChI Key:CNGSOAGKXMNDIO-RGMNGODLSA-N
InChI:InChI=1S/C10H11NO6.Fe/c12-4-6(10(16)17)11-9(15)5-2-1-3-7(13)8(5)14;/h1-3,6,12-14H,4H2,(H,11,15)(H,16,17);/t6-;/m0./s1
CAS number:Not Available
IUPAC Name:(2S)-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxypropanoic acid iron
Traditional IUPAC Name:(2S)-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxypropanoic acid iron
SMILES:[Fe].[H][C@@](CO)(N=C(O)C1=C(O)C(O)=CC=C1)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHippuric acids
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Serine or derivatives
  • Alpha-amino acid or derivatives
  • Salicylamide
  • Salicylic acid or derivatives
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Beta-hydroxy acid
  • Hydroxy acid
  • Vinylogous acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic transition metal salt
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.73 g/LALOGPS
logP0.31ALOGPS
logP0.91ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)-0.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area130.58 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.64 m³·mol⁻¹ChemAxon
Polarizability22.2 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-0cf3af520e5e02e6ac8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-0cf3af520e5e02e6ac8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0090000000-0cf3af520e5e02e6ac8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-c88adadf96c9815bfd70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-c88adadf96c9815bfd70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0090000000-c88adadf96c9815bfd70View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID46926236
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2482
EcoCyc IDCPD0-2482

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 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
General function:
Involved in receptor activity
Specific function:
Not yet known. Postulated to participate in iron transport. Outer membrane receptor for colicins IA and IB
Gene Name:
cirA
Uniprot ID:
P17315
Molecular weight:
73895
General function:
Involved in receptor activity
Specific function:
Involved in the active transport across the outer membrane of iron complexed with catecholate siderophores such as dihydroxybenzoylserine and dihydroxybenzoate. It derives its energy for transport by interacting with the trans-periplasmic membrane protein tonB. Can also transport catechol-substitued cephalosporins. Receptor for microcins M, H47 and E492
Gene Name:
fiu
Uniprot ID:
P75780
Molecular weight:
81960