2.0 2012-05-31 14:48:35 -0600 2015-06-03 17:20:08 -0600 ECMDB20516 M2MDB001325 Ferric coprogen 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) Coprogen C35H53FeN6O13 821.673 821.302002945 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 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 31418-71-0 [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 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-; FQIVLXIUJLOKPL-QYOPVWIVSA-N Cytosol Extra-organism Periplasm logp 2.31 ALOGPS logs -4.51 ALOGPS solubility 2.85e-02 g/l ALOGPS logp -0.32 ChemAxon pka_strongest_acidic 5.29 ChemAxon pka_strongest_basic 3.6 ChemAxon iupac 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 ChemAxon average_mass 821.673 ChemAxon mono_mass 821.302002945 ChemAxon 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 ChemAxon formula C35H53FeN6O13 ChemAxon 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-; ChemAxon inchikey FQIVLXIUJLOKPL-QYOPVWIVSA-N ChemAxon polar_surface_area 294.64 ChemAxon refractivity 194.4 ChemAxon polarizability 78.37 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 15 ChemAxon donor_count 5 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 287935 Specdb::NmrOneD 287936 Specdb::NmrOneD 287937 Specdb::NmrOneD 287938 Specdb::NmrOneD 287939 Specdb::NmrOneD 287940 Specdb::NmrOneD 287941 Specdb::NmrOneD 287942 Specdb::NmrOneD 287943 Specdb::NmrOneD 287944 Specdb::NmrOneD 287945 Specdb::NmrOneD 287946 Specdb::NmrOneD 287947 Specdb::NmrOneD 287948 Specdb::NmrOneD 287949 Specdb::NmrOneD 287950 Specdb::NmrOneD 287951 Specdb::NmrOneD 287952 Specdb::NmrOneD 287953 Specdb::NmrOneD 287954 Specdb::MsMs 1233772 Specdb::MsMs 1233773 Specdb::MsMs 1233774 Specdb::MsMs 1349272 Specdb::MsMs 1349273 Specdb::MsMs 1349274 6449889 4952560 CPD0-621 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. 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. 14756576 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. 16502288 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. 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 Iron(3+)-hydroxamate import ATP-binding protein fhuC P07821 FHUC_ECOLI fhuC http://ecmdb.ca/proteins/P07821.xml Iron(3+)-hydroxamate import system permease protein fhuB P06972 FHUB_ECOLI fhuB http://ecmdb.ca/proteins/P06972.xml Iron(3+)-hydroxamate-binding protein fhuD P07822 FHUD_ECOLI fhuD http://ecmdb.ca/proteins/P07822.xml Iron(3+)-hydroxamate import ATP-binding protein fhuC P07821 FHUC_ECOLI fhuC http://ecmdb.ca/proteins/P07821.xml Iron(3+)-hydroxamate import system permease protein fhuB P06972 FHUB_ECOLI fhuB http://ecmdb.ca/proteins/P06972.xml FhuE receptor P16869 FHUE_ECOLI fhuE http://ecmdb.ca/proteins/P16869.xml Biopolymer transport protein exbB P0ABU7 EXBB_ECOLI exbB http://ecmdb.ca/proteins/P0ABU7.xml Biopolymer transport protein exbD P0ABV2 EXBD_ECOLI exbD http://ecmdb.ca/proteins/P0ABV2.xml Protein tonB P02929 TONB_ECOLI tonB http://ecmdb.ca/proteins/P02929.xml Iron(3+)-hydroxamate-binding protein fhuD P07822 FHUD_ECOLI fhuD http://ecmdb.ca/proteins/P07822.xml 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