Record Information |
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Version | 2.0 |
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Created at | 2021-06-19 22:18:43 UTC |
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Updated at | 2021-06-29 23:59:33 UTC |
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NP-MRD ID | NP0031148 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 9-hydroxy-octadeca-10,12,15-trienoic acid |
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Provided By | JEOL Database |
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Description | 9S-hotre belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, 9S-hotre is considered to be an octadecanoid. 9-hydroxy-octadeca-10,12,15-trienoic acid is found in Apis cerana and Artocarpus communis. 9-hydroxy-octadeca-10,12,15-trienoic acid was first documented in 2000 (PMID: 10830513). Based on a literature review a small amount of articles have been published on 9s-hotre (PMID: 21481031) (PMID: 23370715) (PMID: 23479199). |
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Structure | [H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(O[H])C(\[H])=C(/[H])\C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])[H] InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14,17,19H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3-,8-6-,14-11+/t17-/m1/s1 |
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Synonyms | Value | Source |
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(9S)-(10E,12Z,15Z)-9-Hydroxyoctadecatri-10,12,15-enoic acid | ChEBI | (9S,10E,12Z,15Z)-9-Hydroxyoctadecatrienoic acid | ChEBI | 9(S)-HOT | ChEBI | 9-Hydroxy-10,12,15-octadecatrienoic acid | ChEBI | 9(S)-HOTrE | Kegg | (9S)-(10E,12Z,15Z)-9-Hydroxyoctadecatri-10,12,15-enoate | Generator | (9S,10E,12Z,15Z)-9-Hydroxyoctadecatrienoate | Generator | 9-Hydroxy-10,12,15-octadecatrienoate | Generator | (10E,12Z,15Z)-9-OH-10,12,15-ODTA | MeSH | 9-OH-10,12,15-ODTA | MeSH | 9S-HOTrE | ChEBI |
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Chemical Formula | C18H30O3 |
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Average Mass | 294.4350 Da |
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Monoisotopic Mass | 294.21949 Da |
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IUPAC Name | (9S,10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid |
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Traditional Name | 9(S)-HOTrE |
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CAS Registry Number | Not Available |
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SMILES | [H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(O[H])C(\[H])=C(/[H])\C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14,17,19H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3-,8-6-,14-11+/t17-/m1/s1 |
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InChI Key | RIGGEAZDTKMXSI-MEBVTJQTSA-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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1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. |
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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 | Lineolic acids and derivatives |
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Direct Parent | Lineolic acids and derivatives |
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Alternative Parents | |
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Substituents | - Octadecanoid
- Long-chain fatty acid
- Hydroxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen 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 | - Dong M, Oda Y, Hirota M: (10E,12Z,15Z)-9-hydroxy-10,12,15-octadecatrienoic acid methyl ester as an anti-inflammatory compound from Ehretia dicksonii. Biosci Biotechnol Biochem. 2000 Apr;64(4):882-6. doi: 10.1271/bbb.64.882. [PubMed:10830513 ]
- Lopez MA, Vicente J, Kulasekaran S, Vellosillo T, Martinez M, Irigoyen ML, Cascon T, Bannenberg G, Hamberg M, Castresana C: Antagonistic role of 9-lipoxygenase-derived oxylipins and ethylene in the control of oxidative stress, lipid peroxidation and plant defence. Plant J. 2011 Aug;67(3):447-58. doi: 10.1111/j.1365-313X.2011.04608.x. Epub 2011 Jun 6. [PubMed:21481031 ]
- Vellosillo T, Aguilera V, Marcos R, Bartsch M, Vicente J, Cascon T, Hamberg M, Castresana C: Defense activated by 9-lipoxygenase-derived oxylipins requires specific mitochondrial proteins. Plant Physiol. 2013 Feb;161(2):617-27. doi: 10.1104/pp.112.207514. Epub 2012 Dec 12. [PubMed:23370715 ]
- Saubeau G, Goulitquer S, Barloy D, Potin P, Andrivon D, Val F: Differential induction of oxylipin pathway in potato and tobacco cells by bacterial and oomycete elicitors. Plant Cell Rep. 2013 May;32(5):579-89. doi: 10.1007/s00299-012-1377-y. Epub 2013 Mar 12. [PubMed:23479199 ]
- McLean, S., et al. (1996). McLean, S., et al, Magn. Reson. Chem. 34, 719 (1996). Mag. Reson. Chem..
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