| Record Information |
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| Version | 2.0 |
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| Created at | 2023-12-06 20:00:31 UTC |
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| Updated at | 2025-02-11 15:44:13 UTC |
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| NP-MRD ID | NP0332197 |
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| Natural Product DOI | https://doi.org/10.57994/1370 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 1-O-methoxy-1-oxotetradecan-3-yl 3-[α-l-rhamnopyranosyl-1→2-α-l-rhamnopyranosyl]oxytetradecanoate |
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| Description | 1-O-methoxy-1-oxotetradecan-3-yl 3-[α-l-rhamnopyranosyl-1→2-α-l-rhamnopyranosyl]oxytetradecanoate belongs to the class of organic compounds known as rhamnolipids. These are glycolipids structurally characterized by a glycosyl head group, in this case a rhamnose moiety, and a 3-(hydroxyalkanoyloxy)alkanoic acid (HAA) fatty acid tail. 1-O-methoxy-1-oxotetradecan-3-yl 3-[α-l-rhamnopyranosyl-1→2-α-l-rhamnopyranosyl]oxytetradecanoate was first documented in 2024 (PMID: 38065042). Based on a literature review very few articles have been published on 1-O-methoxy-1-oxotetradecan-3-yl 3-[α-l-rhamnopyranosyl-1→2-α-l-rhamnopyranosyl]oxytetradecanoate. |
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| Structure | CCCCCCCCCCC[C@H](CC(=O)O[C@H](CCCCCCCCCCC)CC(=O)OC)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O InChI=1S/C41H76O13/c1-6-8-10-12-14-16-18-20-22-24-30(26-32(42)49-5)52-33(43)27-31(25-23-21-19-17-15-13-11-9-7-2)53-41-39(37(47)35(45)29(4)51-41)54-40-38(48)36(46)34(44)28(3)50-40/h28-31,34-41,44-48H,6-27H2,1-5H3/t28-,29-,30+,31+,34-,35-,36+,37+,38+,39+,40-,41-/m0/s1 |
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| Synonyms | | Value | Source |
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| 1-O-Methoxy-1-oxotetradecan-3-yl 3-[α-L-rhamnopyranosyl-1→2-α-L-rhamnopyranosyl]oxytetradecanoic acid | Generator |
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| Chemical Formula | C41H76O13 |
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| Average Mass | 777.0460 Da |
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| Monoisotopic Mass | 776.52859 Da |
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| IUPAC Name | (3R)-1-methoxy-1-oxotetradecan-3-yl (3R)-3-{[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}tetradecanoate |
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| Traditional Name | (3R)-1-methoxy-1-oxotetradecan-3-yl (3R)-3-{[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}tetradecanoate |
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| CAS Registry Number | Not Available |
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| SMILES | CCCCCCCCCCC[C@H](CC(=O)O[C@H](CCCCCCCCCCC)CC(=O)OC)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O |
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| InChI Identifier | InChI=1S/C41H76O13/c1-6-8-10-12-14-16-18-20-22-24-30(26-32(42)49-5)52-33(43)27-31(25-23-21-19-17-15-13-11-9-7-2)53-41-39(37(47)35(45)29(4)51-41)54-40-38(48)36(46)34(44)28(3)50-40/h28-31,34-41,44-48H,6-27H2,1-5H3/t28-,29-,30+,31+,34-,35-,36+,37+,38+,39+,40-,41-/m0/s1 |
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| InChI Key | BDHCPAVBOFQCPW-ZKFCBJATSA-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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| NOESY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | TOCSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | 1D_DEPT NMR | 13C NMR Spectrum (1D, 126 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, C5D5N, experimental) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 500.303089352, C5D5deposition_typeN, simulated) | charles.gauthier@inrs.ca | Institut national de la recherche scientifique | Charles Gauthier | 2024-05-03 | View Spectrum |
| | Species |
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| Species of Origin | | Species Name | Source | Reference |
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| Burkholderia lata | | |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as rhamnolipids. These are glycolipids structurally characterized by a glycosyl head group, in this case a rhamnose moiety, and a 3-(hydroxyalkanoyloxy)alkanoic acid (HAA) fatty acid tail. |
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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 acyl glycosides |
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| Direct Parent | Rhamnolipids |
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| Alternative Parents | |
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| Substituents | - Di-rhamnolipid
- Rhamnolipid
- 3-(3-hydroxyalkanoyloxy)alkanoic acid
- Fatty acyl glycoside of mono- or disaccharide
- Fatty alcohol ester
- Alkyl glycoside
- Fatty acid methyl ester
- Fatty acid ester
- Oxane
- Monosaccharide
- Dicarboxylic acid or derivatives
- Methyl ester
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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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| 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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