Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 14:48:35 -0600 |
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Update Date | 2015-06-03 17:20:08 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Ferric coprogen |
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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) |
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Structure | |
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Synonyms: | |
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Chemical Formula: | C35H53FeN6O13 |
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Weight: | Average: 821.673 Monoisotopic: 821.302002945 |
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InChI Key: | FQIVLXIUJLOKPL-QYOPVWIVSA-N |
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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-; |
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CAS number: | 31418-71-0 |
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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 |
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Traditional 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 |
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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 |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | N-acyl-alpha amino acids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State: | Not Available |
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Charge: | 1 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | |
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References |
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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
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | Resource | Link |
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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 |
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