ECMDB: Ferric coprogen (ECMDB20516) (M2MDB001325)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)Transporters (7)XML

Proteins (7)

Record Information

Version

2.0

Creation Date

2012-05-31 14:48:35 -0600

Update Date

2015-06-03 17:20:08 -0600

Secondary Accession Numbers

ECMDB20516

Identification

Name:

Ferric coprogen

Description

Ferric coprogen belongs to the class of Fatty Acid Esters. These are carboxylic ester derivatives of a fatty acid. (inferred from compound structure)Coprogen is involved in iron transportation. The FhuE protein of Escherichia coli functions as the receptor for ferric coprogen and ferric-rhodotorulic acid. (PMID 3032906) The fhuE gene of Escherichia coli encodes the FhuE protein, which is a receptor protein in the coprogen-mediated siderophore iron-transport system. (PMID 16502288) Removal of iron from coprogen, ferrichrome, and ferrioxamine B was significantly lower in fhuF mutants compared to the corresponding parental strains, which suggested that FhuF is involved in iron removal from these hydroxamate-type siderophores. (PMID 14756576) Insertional inactivation and gene replacement of both genes showed that while FhuD2 is involved in the transport of iron(III) in complex with ferrichrome, ferrioxamine B, aerobactin, and coprogen, FhuD1 shows a more limited substrate range, capable of only iron(III)-ferrichrome and iron(III)-ferrioxamine B transport in S. (PMID 11489851)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Coprogen

Chemical Formula:

C₃₅H₅₃FeN₆O₁₃

Weight:

Average: 821.673
Monoisotopic: 821.302002945

InChI Key:

FQIVLXIUJLOKPL-QYOPVWIVSA-N

InChI:

InChI=1S/C35H53N6O13.Fe/c1-23(11-17-42)20-30(45)39(51)14-5-8-27-33(48)38-28(34(49)37-27)9-6-15-40(52)32(47)22-25(3)13-19-54-35(50)29(36-26(4)44)10-7-16-41(53)31(46)21-24(2)12-18-43;/h20-22,27-29,42-43H,5-19H2,1-4H3,(H,36,44)(H,37,49)(H,38,48);/q-3;+3/b23-20-,24-21+,25-22-;

CAS number:

31418-71-0

IUPAC Name:

iron(3+) ion N-(1-{[(3Z)-4-{[3-(3,6-dihydroxy-5-{3-[(2Z)-5-hydroxy-3-methyl-N-oxidopent-2-enamido]propyl}-2,5-dihydropyrazin-2-yl)propyl](oxido)carbamoyl}-3-methylbut-3-en-1-yl]oxy}-5-[(2E)-5-hydroxy-3-methyl-N-oxidopent-2-enamido]-1-oxopentan-2-yl)ethanimidic acid

Traditional IUPAC Name:

SMILES:

[Fe+3].[H]\C(=C(\C)CCO)C(=O)N([O-])CCCC(N=C(C)O)C(=O)OCC\C(C)=C(\[H])C(=O)N([O-])CCCC1N=C(O)C(CCCN([O-])C(=O)C(\[H])=C(\C)CCO)N=C1O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
Fatty acid ester
1,4-diazinane
Piperazine
Fatty acyl
Acetamide
Carboxamide group
Carboxylic acid ester
Lactam
Secondary carboxylic acid amide
Organoheterocyclic compound
Organic transition metal salt
Monocarboxylic acid or derivatives
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic salt
Alcohol
Organooxygen compound
Carbonyl group
Primary alcohol
Organic zwitterion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	2.31	ALOGPS
logP	-0.32	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	5.29	ChemAxon
pKa (Strongest Basic)	3.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	294.64 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	194.4 m³·mol⁻¹	ChemAxon
Polarizability	78.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Adenosine triphosphate + Water + Ferric coprogen > ADP + Ferric coprogen + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Ferric coprogen > ADP + Ferric coprogen + Hydrogen ion + Phosphate
coprogen unloaded (no Fe(III)) + Fe3+ > Ferric coprogen

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-1213109710-305c83889be23469ffa1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-4237029500-df24ac68df840ada3250	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-8294023000-04b77a091e6365fc39df	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-008a-0010001900-593be6585000f38f4166	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001m-2060001900-6ed91bdbd4ad71c97c0b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053u-8182203900-9af0549e149e617b9556	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Cui, Y., Tu, R., Guan, Y., Ma, L., Chen, S. (2006). "Cloning, sequencing, and characterization of the Azospirillum brasilense fhuE gene." Curr Microbiol 52:169-177. Pubmed: 16502288
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Matzanke, B. F., Anemuller, S., Schunemann, V., Trautwein, A. X., Hantke, K. (2004). "FhuF, part of a siderophore-reductase system." Biochemistry 43:1386-1392. Pubmed: 14756576
Sebulsky, M. T., Heinrichs, D. E. (2001). "Identification and characterization of fhuD1 and fhuD2, two genes involved in iron-hydroxamate uptake in Staphylococcus aureus." J Bacteriol 183:4994-5000. Pubmed: 11489851
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	6449889
Kegg ID	Not Available
ChemSpider ID	4952560
Wikipedia ID	Not Available
BioCyc ID	CPD0-621
EcoCyc ID	CPD0-621

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. FhuE receptor

General function:: Involved in receptor activity
Specific function:: Required for the uptake of Fe(3+) via coprogen, ferrioxamine B, and rhodotorulic acid
Gene Name:: fhuE
Uniprot ID:: P16869
Molecular weight:: 81232

Protein Details

4. Biopolymer transport protein exbB

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

Protein Details

5. Biopolymer transport protein exbD

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

Protein Details

6. Protein tonB

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

Protein Details

7. 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

Ferric coprogen (ECMDB20516) (M2MDB001325)

Structure for #<Compound:0xa2c56dfc>

Enzymes

Reactions

Transporters

Reactions