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Record Information
Version2.0
Creation Date2012-07-30 14:54:59 -0600
Update Date2015-06-03 17:20:55 -0600
Secondary Accession Numbers
  • ECMDB21218
Identification
Name:Ferrichrome
DescriptionFerrichrome is a cyclic hexa-peptide that forms a complex with iron atoms. It is a siderophore composed of three glycine and three modified ornithine residues with hydroxamate groups [-N(OH)C(=O)C-]. The 6 oxygen atoms from the three hydroxamate groups bind Fe(III) in near perfect octahedral coordination.
Structure
Thumb
Synonyms:
  • (cyclo{glycyl-N5-(hydroxy-kappaO)-N5-[1-(oxo-kappaO)ethyl]-L-ornithyl-N5-(hydroxy-kappaO)-N5-[1-(oxo-kappaO)ethyl]-L-ornithyl-N5-(hydroxy-kappaO)-N5-[1-(oxo-kappaO)ethyl]-L-ornithylglycylglycyl})iron
  • Ferrichrome
Chemical Formula:C27H42FeN9O12
Weight:Average: 740.52
Monoisotopic: 740.230234986
InChI Key:GGUNGDGGXMHBMJ-UHFFFAOYSA-N
InChI:InChI=1S/C27H42N9O12.Fe/c1-16(37)34(46)10-4-7-19-25(43)30-14-23(41)28-13-22(40)29-15-24(42)31-20(8-5-11-35(47)17(2)38)26(44)33-21(27(45)32-19)9-6-12-36(48)18(3)39;/h19-21H,4-15H2,1-3H3,(H,28,41)(H,29,40)(H,30,43)(H,31,42)(H,32,45)(H,33,44);/q-3;+3
CAS number:15630-64-5
IUPAC Name:1-{3,29-diacetyl-9,12,15,18,21,34-hexahydroxy-2,27,28-trioxa-3,8,11,14,17,20,26,29,33-nonaaza-1-ferratricyclo[17.8.5.2⁷,²²]tetratriaconta-8,11,14,17,20,33-hexaen-26-yl}ethan-1-one
Traditional IUPAC Name:1-{3,29-diacetyl-9,12,15,18,21,34-hexahydroxy-2,27,28-trioxa-3,8,11,14,17,20,26,29,33-nonaaza-1-ferratricyclo[17.8.5.2⁷,²²]tetratriaconta-8,11,14,17,20,33-hexaen-26-yl}ethanone
SMILES:CC(=O)N1CCCC2N=C(O)CN=C(O)CN=C(O)CN=C(O)C3CCCN(O[Fe](O1)ON(CCCC(N=C2O)C(O)=N3)C(C)=O)C(C)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Cyclic alpha peptide
  • Macrolactam
  • Alpha-amino acid or derivatives
  • Acetamide
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Azacycle
  • Organic transition metal salt
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic zwitterion
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP0.04ALOGPS
logP0.34ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)4.67ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area284.16 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity161.55 m³·mol⁻¹ChemAxon
Polarizability68.22 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-007p-5100009800-61df59dd98d6f2e41c67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052e-0000009300-b583c6f94c3a0da588baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-9000011000-72823dc2e3ac08c3a175View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-0000009500-61e1d971f25a45d3f738View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0103-1000039200-8e12f4c7be4f72b0c9edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05g4-4000149400-8418412bb70a903830e8View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID5019
HMDB IDNot Available
Pubchem Compound ID644251
Kegg IDC06228
ChemSpider ID25520
WikipediaFerrichrome
BioCyc IDCPD0-2241
EcoCyc IDCPD0-2241

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for energy coupling to the transport system
Gene Name:
fhuC
Uniprot ID:
P07821
Molecular weight:
28886
Reactions
ATP + H(2)O + iron chelate(Out) = ADP + phosphate + iron chelate(In).
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for the translocation of the substrate across the membrane
Gene Name:
fhuB
Uniprot ID:
P06972
Molecular weight:
70422
General function:
Involved in binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Binds the iron(3+)-hydroxamate complex and transfers it to the membrane-bound permease. Required for the transport of all iron(3+)-hydroxamate siderophores such as ferrichrome, gallichrome, desferrioxamine, coprogen, aerobactin, shizokinen, rhodotorulic acid and the antibiotic albomycin
Gene Name:
fhuD
Uniprot ID:
P07822
Molecular weight:
32998

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for energy coupling to the transport system
Gene Name:
fhuC
Uniprot ID:
P07821
Molecular weight:
28886
Reactions
ATP + H(2)O + iron chelate(Out) = ADP + phosphate + iron chelate(In).
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Responsible for the translocation of the substrate across the membrane
Gene Name:
fhuB
Uniprot ID:
P06972
Molecular weight:
70422
General function:
Involved in receptor activity
Specific function:
This receptor binds the ferrichrome-iron ligand. It interacts with the tonB protein, which is responsible for energy coupling of the ferrichrome-promoted iron transport system. Acts as a receptor for bacteriophage T5 as well as T1, phi80 and colicin M. Binding of T5 triggers the opening of a high conductance ion channel. Can also transport the antibiotic albomycin
Gene Name:
fhuA
Uniprot ID:
P06971
Molecular weight:
82182
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 binding
Specific function:
Part of the ABC transporter complex fhuCDB involved in iron(3+)-hydroxamate import. Binds the iron(3+)-hydroxamate complex and transfers it to the membrane-bound permease. Required for the transport of all iron(3+)-hydroxamate siderophores such as ferrichrome, gallichrome, desferrioxamine, coprogen, aerobactin, shizokinen, rhodotorulic acid and the antibiotic albomycin
Gene Name:
fhuD
Uniprot ID:
P07822
Molecular weight:
32998