Record Information
Version2.0
Creation Date2012-07-30 14:54:58 -0600
Update Date2015-06-03 17:20:54 -0600
Secondary Accession Numbers
  • ECMDB21213
Identification
Name:Fe(III)dicitrate
DescriptionFe(iii)dicitrate is the complex formed between iron(III) and citrate. It is a substrate for the E. coli transport protein known as FecA. FecA is the outer membrane receptor protein in the Fe3+ dicitrate transport system.
Structure
Thumb
Synonyms:
  • Fe(III)dicitrate
  • Fe(III)dicitric acid
  • Ferric dicitrate complex
  • Ferric dicitric acid complex
  • Iron (III) dicitrate
  • Iron (III) dicitric acid
  • Iron dicitrate
  • Iron dicitric acid
  • Iron(III)dicitrate
  • Iron(III)dicitric acid
  • {3-[(R)-hydroxy(hydroxy-kappaO)methyl]pentane-1,1,3,5,5-pentolato(3)-kappa2O1,O5}{3-[(S)-hydroxy(hydroxy-kappaO)methyl]pentane-1,1,3,5,5-pentolato(3-)-kappa2O1,O5}iron
Chemical Formula:C12H28FeO14
Weight:Average: 452.187
Monoisotopic: 452.082847737
InChI Key:BWHIDISYXGEZJU-UHFFFAOYSA-N
InChI:InChI=1S/2C6H14O7.Fe/c2*7-3(8)1-6(13,5(11)12)2-4(9)10;/h2*3-5,7-13H,1-2H2;
CAS number:Not Available
IUPAC Name:bis(3-(dihydroxymethyl)pentane-1,1,3,5,5-pentol) iron
Traditional IUPAC Name:bis(3-(dihydroxymethyl)pentane-1,1,3,5,5-pentol) iron
SMILES:[Fe].OC(O)CC(O)(CC(O)O)C(O)O.OC(O)CC(O)(CC(O)O)C(O)O
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Tertiary alcohol
  • Organic transition metal salt
  • 1,1-diol
  • Polyol
  • Carbonyl hydrate
  • Hydrocarbon derivative
  • Organic salt
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
logP-3.2ChemAxon
pKa (Strongest Acidic)11.13ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area141.61 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity38.69 m³·mol⁻¹ChemAxon
Polarizability17.47 ųChemAxon
Number of Rings0ChemAxon
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, Positivesplash10-0udi-0000900000-2520f3b30a5864d90710View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000900000-2520f3b30a5864d90710View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0000900000-2520f3b30a5864d90710View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-acb20658066243e1a640View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-acb20658066243e1a640View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0000900000-acb20658066243e1a640View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID4991
HMDB IDNot Available
Pubchem Compound ID440954
Kegg IDC06229
ChemSpider ID389781
Wikipedia IDNot Available
BioCyc IDFERRIC-CITRATE-COMPLEX
EcoCyc IDFERRIC-CITRATE-COMPLEX

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for energy coupling to the transport system
Gene Name:
fecE
Uniprot ID:
P15031
Molecular weight:
28191
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for the translocation of the substrate across the membrane
Gene Name:
fecD
Uniprot ID:
P15029
Molecular weight:
34131
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for the translocation of the substrate across the membrane
Gene Name:
fecC
Uniprot ID:
P15030
Molecular weight:
34892
General function:
Involved in binding
Specific function:
Binds citrate-dependent Fe(3+); part of the binding- protein-dependent transport system for uptake of citrate-dependent Fe(3+)
Gene Name:
fecB
Uniprot ID:
P15028
Molecular weight:
33146

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for energy coupling to the transport system
Gene Name:
fecE
Uniprot ID:
P15031
Molecular weight:
28191
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for the translocation of the substrate across the membrane
Gene Name:
fecD
Uniprot ID:
P15029
Molecular weight:
34131
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for citrate-dependent Fe(3+). Probably responsible for the translocation of the substrate across the membrane
Gene Name:
fecC
Uniprot ID:
P15030
Molecular weight:
34892
General function:
Involved in receptor activity
Specific function:
FecA is the outer membrane receptor protein in the Fe(3+) dicitrate transport system
Gene Name:
fecA
Uniprot ID:
P13036
Molecular weight:
85321
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 binding
Specific function:
Binds citrate-dependent Fe(3+); part of the binding- protein-dependent transport system for uptake of citrate-dependent Fe(3+)
Gene Name:
fecB
Uniprot ID:
P15028
Molecular weight:
33146
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