Record Information |
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Version | 2.0 |
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Created at | 2020-12-09 02:11:11 UTC |
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Updated at | 2021-07-15 16:50:06 UTC |
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NP-MRD ID | NP0004766 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Autoinducer I |
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Provided By | NPAtlas |
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Description | N-(3-oxohexanoyl)-L-homoserine lactone is also known as (S)-3-(3-ketohexanamido)-2-oxotetrahydrofuran or (S)-3-(3-ketohexanamido)butyrolactone. Autoinducer I is found in Azospirillum lipoferum, Erwinia and Pectobacterium carotovorum. Autoinducer I was first documented in 1992 (PMID: 1335238). Based on a literature review a small amount of articles have been published on N-(3-oxohexanoyl)-L-homoserine lactone (PMID: 34413838) (PMID: 33321169) (PMID: 32717872) (PMID: 32457732). |
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Structure | [H]N(C(=O)C([H])([H])C(=O)C([H])([H])C([H])([H])C([H])([H])[H])[C@]1([H])C(=O)OC([H])([H])C1([H])[H] InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)/t8-/m0/s1 |
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Synonyms | Value | Source |
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(S)-3-(3-Ketohexanamido)-2-oxotetrahydrofuran | ChEBI | (S)-3-(3-Ketohexanamido)butyrolactone | ChEBI | (S)-3-(3-Oxohexanamido)-2-oxotetrahydrofuran | ChEBI | (S)-3-(3-Oxohexanamido)butyrolactone | ChEBI | N-(3-Ketocaproyl)-L-homoserine lactone | ChEBI | N-(3-Ketohexanoyl)-L-homoserine lactone | ChEBI | N-(beta-Ketocaproyl)-L-homoserine lactone | ChEBI | N-(b-Ketocaproyl)-L-homoserine lactone | Generator | N-(Β-ketocaproyl)-L-homoserine lactone | Generator | 3-oxo-C6-AHL | MeSH | Luciferase autoinducer | MeSH | AI-1 lactone | MeSH | N-(3-Oxohexanoyl)-3-aminodihydro-2(3H)-furanone | MeSH | N-(beta-Ketocaproyl)homoserine lactone | MeSH | Autoinducer 1 | MeSH | N-(3-Oxohexanoyl)homoserine lactone | MeSH | N-3-Oxohexanoyl-L-homoserine lactone | MeSH | OHHL-N | MeSH | VAI-1 | MeSH |
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Chemical Formula | C10H15NO4 |
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Average Mass | 213.2330 Da |
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Monoisotopic Mass | 213.10011 Da |
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IUPAC Name | 3-oxo-N-[(3S)-2-oxooxolan-3-yl]hexanamide |
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Traditional Name | 3-oxo-N-[(3S)-2-oxooxolan-3-yl]hexanamide |
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CAS Registry Number | Not Available |
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SMILES | CCCC(=O)CC(=O)N[C@H]1CCOC1=O |
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InChI Identifier | InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)/t8-/m0/s1 |
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InChI Key | YRYOXRMDHALAFL-QMMMGPOBSA-N |
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Experimental Spectra |
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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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
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Chemical Shift Submissions |
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| Not Available |
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Species |
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Species of Origin | |
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Chemical Taxonomy |
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Classification | Not classified |
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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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External Links |
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NPAtlas ID | NPA003620 |
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HMDB ID | Not Available |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 599950 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | Not Available |
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PDB ID | Not Available |
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ChEBI ID | 63789 |
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Good Scents ID | Not Available |
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References |
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General References | - Bainton NJ, Stead P, Chhabra SR, Bycroft BW, Salmond GP, Stewart GS, Williams P: N-(3-oxohexanoyl)-L-homoserine lactone regulates carbapenem antibiotic production in Erwinia carotovora. Biochem J. 1992 Dec 15;288 ( Pt 3):997-1004. doi: 10.1042/bj2880997. [PubMed:1335238 ]
- Zhang W, Fan X, Li J, Ye T, Mishra S, Zhang L, Chen S: Exploration of the Quorum-Quenching Mechanism in Pseudomonas nitroreducens W-7 and Its Potential to Attenuate the Virulence of Dickeya zeae EC1. Front Microbiol. 2021 Aug 3;12:694161. doi: 10.3389/fmicb.2021.694161. eCollection 2021. [PubMed:34413838 ]
- Molnar M, Fenyvesi E, Berkl Z, Nemeth I, Fekete-Kertesz I, Marton R, Vaszita E, Varga E, Ujj D, Szente L: Cyclodextrin-mediated quorum quenching in the Aliivibrio fischeri bioluminescence model system - Modulation of bacterial communication. Int J Pharm. 2021 Feb 1;594:120150. doi: 10.1016/j.ijpharm.2020.120150. Epub 2020 Dec 13. [PubMed:33321169 ]
- Zhang W, Luo Q, Zhang Y, Fan X, Ye T, Mishra S, Bhatt P, Zhang L, Chen S: Quorum Quenching in a Novel Acinetobacter sp. XN-10 Bacterial Strain against Pectobacterium carotovorum subsp. carotovorum. Microorganisms. 2020 Jul 23;8(8). pii: microorganisms8081100. doi: 10.3390/microorganisms8081100. [PubMed:32717872 ]
- Fan X, Ye T, Li Q, Bhatt P, Zhang L, Chen S: Potential of a Quorum Quenching Bacteria Isolate Ochrobactrum intermedium D-2 Against Soft Rot Pathogen Pectobacterium carotovorum subsp. carotovorum. Front Microbiol. 2020 May 8;11:898. doi: 10.3389/fmicb.2020.00898. eCollection 2020. [PubMed:32457732 ]
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