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Ferrichrome minus Fe(III) (M2MDB001625)

Record Information
Version2.0
Creation Date2012-07-30 14:54:58 -0600
Update Date2015-06-03 17:20:54 -0600
Secondary Accession Numbers
  • ECMDB21217
Identification
Name:Ferrichrome minus Fe(III)
DescriptionFerrichrome minus Fe(iii) 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. Ferrichrome is produced by several different fungi, but used by bacteria in iron transport.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Ferrichrome
  • Ferrichrome minus Fe(III)
  • Iron-free ferrichrome
Chemical Formula:C27H42N9O12
Weight:Average: 684.6755
Monoisotopic: 684.295292853
InChI Key:GNGZPAKHDVFMFC-UHFFFAOYSA-N
InChI:InChI=1S/C27H42N9O12/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
CAS number:Not Available
IUPAC Name:N-(3-{3,6,9,12,15,18-hexahydroxy-5,17-bis[3-(N-oxidoacetamido)propyl]-1,4,7,10,13,16-hexaazacyclooctadeca-1(18),3,6,9,12,15-hexaen-2-yl}propyl)-N-oxidoacetamide
Traditional IUPAC Name:N-(3-{3,6,9,12,15,18-hexahydroxy-5,17-bis[3-(N-oxidoacetamido)propyl]-1,4,7,10,13,16-hexaazacyclooctadeca-1(18),3,6,9,12,15-hexaen-2-yl}propyl)-N-oxidoacetamide
SMILES:CC(=O)N([O-])CCCC1N=C(O)C(CCCN([O-])C(C)=O)N=C(O)C(CCCN([O-])C(C)=O)N=C(O)CN=C(O)CN=C(O)CN=C1O
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
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP-0.06ALOGPS
logP-2.3ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.64ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area325.65 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity161.83 m³·mol⁻¹ChemAxon
Polarizability66.89 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Fe3+ + Ferrichrome minus Fe(III) > Ferrichrome
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, Positivesplash10-000i-0000009000-732d5578818c0120c631View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1000009000-a20b323bad91cb6b7a39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9101001000-274b9542770240dea530View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2000009000-b365b94e87dda5b15926View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-9100007000-b48a5deae09293c4ee5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9721113000-f1d14639d40c532d7e44View 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 ID27425
Kegg IDNot Available
ChemSpider ID25521
Wikipedia IDNot Available
BioCyc IDCPD0-2205
EcoCyc IDCPD0-2205

Enzymes

Protein Details
1. Iron(3+)-hydroxamate import ATP-binding protein fhuC
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).
Protein Details
2. Iron(3+)-hydroxamate import system permease protein fhuB
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
Protein Details
3. Iron(3+)-hydroxamate-binding protein fhuD
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

Protein Details
1. Iron(3+)-hydroxamate import ATP-binding protein fhuC
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).
Protein Details
2. Iron(3+)-hydroxamate import system permease protein fhuB
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
Protein Details
3. Ferrichrome-iron receptor
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
Protein Details
4. Iron(3+)-hydroxamate-binding protein fhuD
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