Record Information |
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Version | 2.0 |
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Created at | 2022-12-13 18:21:16 UTC |
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Updated at | 2024-09-03 04:14:55 UTC |
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NP-MRD ID | NP0331213 |
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Natural Product DOI | https://doi.org/10.57994/0090 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Desferricoprogen |
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Description | Desferricoprogen 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. Desferricoprogen was first documented in 2004 (PMID: 15522421). Based on a literature review a significant number of articles have been published on desferricoprogen (PMID: 28058837) (PMID: 22687412) (PMID: 31152280) (PMID: 36993360) (PMID: 32635347) (PMID: 30016095). |
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Structure | CC(=O)N[C@@H](CCCN(O)C(=O)\C=C(/C)CCO)C(=O)OCC\C(C)=C\C(=O)N(O)CCC[C@@H]1NC(=O)[C@H](CCCN(O)C(=O)\C=C(/C)CCO)NC1=O InChI=1S/C35H56N6O13/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/h20-22,27-29,42-43,51-53H,5-19H2,1-4H3,(H,36,44)(H,37,49)(H,38,48)/b23-20+,24-21+,25-22+/t27-,28-,29-/m0/s1 |
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Synonyms | Value | Source |
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N-alpha-Acetylfusarinines | MeSH |
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Chemical Formula | C35H56N6O13 |
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Average Mass | 768.8620 Da |
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Monoisotopic Mass | 768.39054 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)N[C@@H](CCCN(O)C(=O)\C=C(/C)CCO)C(=O)OCC\C(C)=C\C(=O)N(O)CCC[C@@H]1NC(=O)[C@H](CCCN(O)C(=O)\C=C(/C)CCO)NC1=O |
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InChI Identifier | InChI=1S/C35H56N6O13/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/h20-22,27-29,42-43,51-53H,5-19H2,1-4H3,(H,36,44)(H,37,49)(H,38,48)/b23-20+,24-21+,25-22+/t27-,28-,29-/m0/s1 |
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InChI Key | AKLLFACZGZTMGS-FCRFISLRSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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ROESY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | a.salim@uq.edu.au | Not Available | Not Available | 2022-12-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental) | a.salim@uq.edu.au | Not Available | Not Available | 2022-12-13 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | a.salim@uq.edu.au | Not Available | Not Available | 2022-12-13 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | a.salim@uq.edu.au | Not Available | Not Available | 2022-12-13 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | a.salim@uq.edu.au | Not Available | Not Available | 2022-12-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental) | a.salim@uq.edu.au | Not Available | Not Available | 2022-12-13 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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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
- Hydroxamic acid
- Lactam
- Secondary carboxylic acid amide
- Monocarboxylic acid or derivatives
- Azacycle
- Organoheterocyclic compound
- Organonitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic nitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Primary alcohol
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Kalansuriya P, Quezada M, Esposito BP, Capon RJ: Talarazines A-E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045). J Nat Prod. 2017 Mar 24;80(3):609-615. doi: 10.1021/acs.jnatprod.6b00889. Epub 2017 Jan 6. [PubMed:28058837 ]
- Funahashi T, Tanabe T, Mihara K, Miyamoto K, Tsujibo H, Yamamoto S: Identification and characterization of an outer membrane receptor gene in Acinetobacter baumannii required for utilization of desferricoprogen, rhodotorulic acid, and desferrioxamine B as xenosiderophores. Biol Pharm Bull. 2012;35(5):753-60. doi: 10.1248/bpb.35.753. [PubMed:22687412 ]
- da Silva GS, Shang Z, Kalansuriya P, Capon RJ, Esposito BP: Antioxidant activity and cellular uptake of the hydroxamate-based fungal iron chelators pyridoxatin, desferriastechrome and desferricoprogen. Biometals. 2019 Aug;32(4):707-715. doi: 10.1007/s10534-019-00202-7. Epub 2019 Jun 1. [PubMed:31152280 ]
- Luu GT, Little JC, Pierce EC, Morin M, Ertekin CA, Wolfe BE, Baars O, Dutton RJ, Sanchez LM: Metabolomics of bacterial-fungal pairwise interactions reveal conserved molecular mechanisms. bioRxiv. 2023 Mar 13:2023.03.13.532449. doi: 10.1101/2023.03.13.532449. Preprint. [PubMed:36993360 ]
- Potor L, Eva SK, Hegedus H, Petho D, Szabo Z, Szigeti ZM, Pocsi I, Trencsenyi G, Szikra D, Garai I, Gall T, Combi Z, Kappelmayer J, Balla G, Balla J: The Fungal Iron Chelator Desferricoprogen Inhibits Atherosclerotic Plaque Formation. Int J Mol Sci. 2020 Jul 3;21(13):4746. doi: 10.3390/ijms21134746. [PubMed:32635347 ]
- Prescott TAK, Jaeg T, Hoepfner D: Yeast Chemogenomic Profiling Reveals Iron Chelation To Be the Principle Cell Inhibitory Mode of Action of Gossypol. J Med Chem. 2018 Aug 23;61(16):7381-7386. doi: 10.1021/acs.jmedchem.8b00692. Epub 2018 Aug 6. [PubMed:30016095 ]
- Farkas E, Buglyo P: Lead(II) Complexes of Amino Acids, Peptides, and Other Related Ligands of Biological Interest. Met Ions Life Sci. 2017 Apr 10;17:/books/9783110434330/9783110434330-008/9783110434330-008.xml. doi: 10.1515/9783110434330-008. [PubMed:28731301 ]
- Vartoukian SR, Moazzez RV, Paster BJ, Dewhirst FE, Wade WG: First Cultivation of Health-Associated Tannerella sp. HOT-286 (BU063). J Dent Res. 2016 Oct;95(11):1308-13. doi: 10.1177/0022034516651078. Epub 2016 May 18. [PubMed:27193146 ]
- Vartoukian SR, Adamowska A, Lawlor M, Moazzez R, Dewhirst FE, Wade WG: In Vitro Cultivation of 'Unculturable' Oral Bacteria, Facilitated by Community Culture and Media Supplementation with Siderophores. PLoS One. 2016 Jan 14;11(1):e0146926. doi: 10.1371/journal.pone.0146926. eCollection 2016. [PubMed:26764907 ]
- Farkas E, Szabo O, Parajdi-Losonczi PL, Balla G, Pocsi I: Mn(II)/Mn(III) and Fe(III) binding capability of two Aspergillus fumigatus siderophores, desferricrocin and N', N'', N'''-triacetylfusarinine C. J Inorg Biochem. 2014 Oct;139:30-7. doi: 10.1016/j.jinorgbio.2014.06.005. Epub 2014 Jun 11. [PubMed:24959697 ]
- Tircso G, Garda Z, Kalman FK, Baranyai Z, Pocsi I, Balla G, Toth I: Lanthanide(III) complexes of some natural siderophores: a thermodynamic, kinetic and relaxometric study. J Inorg Biochem. 2013 Oct;127:53-61. doi: 10.1016/j.jinorgbio.2013.06.006. Epub 2013 Jun 18. [PubMed:23850669 ]
- Pocsi I, Jeney V, Kertai P, Pocsi I, Emri T, Gyemant G, Fesus L, Balla J, Balla G: Fungal siderophores function as protective agents of LDL oxidation and are promising anti-atherosclerotic metabolites in functional food. Mol Nutr Food Res. 2008 Dec;52(12):1434-47. doi: 10.1002/mnfr.200700467. [PubMed:18646004 ]
- Farkas E, Batka D, Kremper G, Pocsi I: Structure-based differences between the metal ion selectivity of two siderophores desferrioxamine B (DFB) and desferricoprogen (DFC): why DFC is much better Pb(II) sequestering agent than DFB? J Inorg Biochem. 2008 Aug;102(8):1654-9. doi: 10.1016/j.jinorgbio.2008.03.006. Epub 2008 Apr 1. [PubMed:18486225 ]
- Enyedy EA, Pocsi I, Farkas E: Complexation of desferricoprogen with trivalent Fe, Al, Ga, In and divalent Fe, Ni, Cu, Zn metal ions: effects of the linking chain structure on the metal binding ability of hydroxamate based siderophores. J Inorg Biochem. 2004 Nov;98(11):1957-66. doi: 10.1016/j.jinorgbio.2004.08.017. [PubMed:15522421 ]
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