Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 03:15:27 UTC |
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Updated at | 2022-09-11 03:15:27 UTC |
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NP-MRD ID | NP0309012 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 2-hydroxy-3-({3-[(2e)-n-hydroxydec-2-enamido]propyl}-c-hydroxycarbonimidoyl)-2-({[3-(n-hydroxyacetamido)propyl]-c-hydroxycarbonimidoyl}methyl)propanoic acid |
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Description | Rhizobactin 1021 belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. It was first documented in 2006 (PMID: 16549659). Based on a literature review a significant number of articles have been published on rhizobactin 1021 (PMID: 25887945) (PMID: 23378574) (PMID: 22328673) (PMID: 20210991). |
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Structure | CCCCCCC\C=C\C(=O)N(O)CCCN=C(O)CC(O)(CC(O)=NCCCN(O)C(C)=O)C(O)=O InChI=1S/C24H42N4O9/c1-3-4-5-6-7-8-9-12-22(32)28(37)16-11-14-26-21(31)18-24(35,23(33)34)17-20(30)25-13-10-15-27(36)19(2)29/h9,12,35-37H,3-8,10-11,13-18H2,1-2H3,(H,25,30)(H,26,31)(H,33,34)/b12-9+ |
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Synonyms | Value | Source |
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Rhizobactin-1021 | ChEBI |
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Chemical Formula | C24H42N4O9 |
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Average Mass | 530.6190 Da |
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Monoisotopic Mass | 530.29518 Da |
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IUPAC Name | 2-hydroxy-3-({3-[(2E)-N-hydroxydec-2-enamido]propyl}-C-hydroxycarbonimidoyl)-2-({[3-(N-hydroxyacetamido)propyl]-C-hydroxycarbonimidoyl}methyl)propanoic acid |
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Traditional Name | 2-hydroxy-3-({3-[(2E)-N-hydroxydec-2-enamido]propyl}-C-hydroxycarbonimidoyl)-2-({[3-(N-hydroxyacetamido)propyl]-C-hydroxycarbonimidoyl}methyl)propanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCC\C=C\C(=O)N(O)CCCN=C(O)CC(O)(CC(O)=NCCCN(O)C(C)=O)C(O)=O |
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InChI Identifier | InChI=1S/C24H42N4O9/c1-3-4-5-6-7-8-9-12-22(32)28(37)16-11-14-26-21(31)18-24(35,23(33)34)17-20(30)25-13-10-15-27(36)19(2)29/h9,12,35-37H,3-8,10-11,13-18H2,1-2H3,(H,25,30)(H,26,31)(H,33,34)/b12-9+ |
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InChI Key | WRSKPFYPBJAAEG-FMIVXFBMSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| 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 hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Hydroxy fatty acids |
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Alternative Parents | |
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Substituents | - Branched fatty acid
- Hydroxy fatty acid
- Alpha-hydroxy acid
- Fatty amide
- Hydroxy acid
- N-acyl-amine
- Acetohydroxamic acid
- Acetamide
- Tertiary alcohol
- Carboxamide group
- Hydroxamic acid
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic 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 | - Amaya-Gomez CV, Hirsch AM, Soto MJ: Biofilm formation assessment in Sinorhizobium meliloti reveals interlinked control with surface motility. BMC Microbiol. 2015 Mar 3;15:58. doi: 10.1186/s12866-015-0390-z. [PubMed:25887945 ]
- Funahashi T, Tanabe T, Maki J, Miyamoto K, Tsujibo H, Yamamoto S: Identification and characterization of a cluster of genes involved in biosynthesis and transport of acinetoferrin, a siderophore produced by Acinetobacter haemolyticus ATCC 17906T. Microbiology (Reading). 2013 Apr;159(Pt 4):678-690. doi: 10.1099/mic.0.065177-0. Epub 2013 Feb 1. [PubMed:23378574 ]
- Nogales J, Bernabeu-Roda L, Cuellar V, Soto MJ: ExpR is not required for swarming but promotes sliding in Sinorhizobium meliloti. J Bacteriol. 2012 Apr;194(8):2027-35. doi: 10.1128/JB.06524-11. Epub 2012 Feb 10. [PubMed:22328673 ]
- Nogales J, Dominguez-Ferreras A, Amaya-Gomez CV, van Dillewijn P, Cuellar V, Sanjuan J, Olivares J, Soto MJ: Transcriptome profiling of a Sinorhizobium meliloti fadD mutant reveals the role of rhizobactin 1021 biosynthesis and regulation genes in the control of swarming. BMC Genomics. 2010 Mar 8;11:157. doi: 10.1186/1471-2164-11-157. [PubMed:20210991 ]
- Cuiv PO, Clarke P, O'Connell M: Identification and characterization of an iron-regulated gene, chtA, required for the utilization of the xenosiderophores aerobactin, rhizobactin 1021 and schizokinen by Pseudomonas aeruginosa. Microbiology (Reading). 2006 Apr;152(Pt 4):945-954. doi: 10.1099/mic.0.28552-0. [PubMed:16549659 ]
- LOTUS database [Link]
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