Record Information |
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Version | 2.0 |
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Created at | 2022-04-28 01:09:45 UTC |
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Updated at | 2022-04-28 01:09:46 UTC |
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NP-MRD ID | NP0054970 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 18-Hydroxy-9-octadecenoic acid |
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Description | 18-Hydroxyoleic acid, also known as 19-home(9Z) or omega-hydroxyoleate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 18-Hydroxyoleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 18-Hydroxy-9-octadecenoic acid is found in Arabidopsis thaliana. 18-Hydroxy-9-octadecenoic acid was first documented in 1973 (PMID: 4356240). An omega-hydroxy fatty acid that is 18-hydroxyoctadecanoic acid which has been dehydrogenated to introduce a trans double bond at the 9-10 position (PMID: 24673591) (PMID: 23205954). |
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Structure | [H]\C(CCCCCCCCO)=C(/[H])CCCCCCCC(O)=O InChI=1S/C18H34O3/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h1-2,19H,3-17H2,(H,20,21)/b2-1- |
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Synonyms | Value | Source |
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(9Z)-18-Hydroxyoctadecenoic acid | ChEBI | 18-Hydroxy-9-octadecenoic acid | ChEBI | 18-Hydroxy-9Z-octadecenoic acid | ChEBI | 19-HOME(9Z) | ChEBI | Omega-hydroxy-(9Z)-octadecenoic acid | ChEBI | Omega-hydroxyoleic acid | ChEBI | (9Z)-18-Hydroxyoctadecenoate | Generator | 18-Hydroxy-9-octadecenoate | Generator | 18-Hydroxy-9Z-octadecenoate | Generator | Omega-hydroxy-(9Z)-octadecenoate | Generator | Omega-hydroxyoleate | Generator | 18-Hydroxyoleate | Generator |
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Chemical Formula | C18H34O3 |
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Average Mass | 298.4670 Da |
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Monoisotopic Mass | 298.25079 Da |
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IUPAC Name | (9Z)-18-hydroxyoctadec-9-enoic acid |
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Traditional Name | (9Z)-18-hydroxyoctadec-9-enoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]\C(CCCCCCCCO)=C(/[H])CCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C18H34O3/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h1-2,19H,3-17H2,(H,20,21)/b2-1- |
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InChI Key | LQUHZVLTTWMBTO-UPHRSURJSA-N |
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Experimental Spectra |
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| Not Available |
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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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Description | Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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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 | Long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Long-chain fatty acid
- Hydroxy fatty acid
- Unsaturated fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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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External Links |
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HMDB ID | HMDB0155793 |
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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 | C00007439 |
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Chemspider ID | Not Available |
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KEGG Compound ID | C19616 |
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BioCyc ID | 18-HYDROXYOLEATE |
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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 | 5312773 |
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PDB ID | Not Available |
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ChEBI ID | 79312 |
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Good Scents ID | Not Available |
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References |
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General References | - Belge B, Llovera M, Comabella E, Graell J, Lara I: Fruit cuticle composition of a melting and a nonmelting peach cultivar. J Agric Food Chem. 2014 Apr 16;62(15):3488-95. doi: 10.1021/jf5003528. Epub 2014 Apr 4. [PubMed:24673591 ]
- Shi JX, Adato A, Alkan N, He Y, Lashbrooke J, Matas AJ, Meir S, Malitsky S, Isaacson T, Prusky D, Leshkowitz D, Schreiber L, Granell AR, Widemann E, Grausem B, Pinot F, Rose JKC, Rogachev I, Rothan C, Aharoni A: The tomato SlSHINE3 transcription factor regulates fruit cuticle formation and epidermal patterning. New Phytol. 2013 Jan;197(2):468-480. doi: 10.1111/nph.12032. Epub 2012 Dec 3. [PubMed:23205954 ]
- Kolattukudy PE, Walton TJ, Kushwaha RP: Biosynthesis of the C18 family of cutin acids: omega-hydroxyoleic acid, omega-hydroxy-9,10-epoxystearic acid, 9,10,18-trihydroxystearic acid, and their delta12-unsaturated analogs. Biochemistry. 1973 Oct 23;12(22):4488-98. doi: 10.1021/bi00746a029. [PubMed:4356240 ]
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