| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-08 19:08:09 UTC |
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| Updated at | 2022-09-08 19:08:10 UTC |
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| NP-MRD ID | NP0272493 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (9z)-octadec-9-enimidic acid |
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| Description | Oleamide, also known as amide O or oleyl amide, belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. Thus, oleamide is considered to be a fatty amide lipid molecule. A fatty amide derived from oleic acid. (9z)-octadec-9-enimidic acid is found in Desmos cochinchinensis, Glycine max, Pseudo-nitzschia multistriata, Trypanosoma brucei and Vitis vinifera. (9z)-octadec-9-enimidic acid was first documented in 2001 (PMID: 11681856). Oleamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 17445087) (PMID: 24253045). |
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| Structure | CCCCCCCC\C=C/CCCCCCCC(N)=O InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9- |
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| Synonyms | | Value | Source |
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| (9Z)-9-Octadecenamide | ChEBI | | (9Z)-Octadecenamide | ChEBI | | (Z)-9-Octadecenamide | ChEBI | | (Z)-Octadec-9-enoic acid amide | ChEBI | | 9-Octadecenamide | ChEBI | | 9Z-Octadecenamide | ChEBI | | cis-9,10-Octadecenoamide | ChEBI | | Oleic acid amide | ChEBI | | Oleyl amide | ChEBI | | Oleylamide | ChEBI | | (Z)-Octadec-9-enoate amide | Generator | | Oleate amide | Generator | | (9Z)-Octadec-9-enamide | HMDB | | (cis)-9-Octadecenoate | HMDB | | (cis)-9-Octadecenoic acid | HMDB | | (cis)-9-Octadecenoic acid amide | HMDB | | 14C-Labeled oleamide | HMDB | | 9,10-Octadecenamide | HMDB | | Adogen 73 | HMDB | | Aliphatic amide | HMDB | | Amide O | HMDB | | Armid O | HMDB | | Armoslip CP | HMDB | | Crodamide O | HMDB | | Crodamide or | HMDB | | Diamide O 200 | HMDB | | Diamit O 200 | HMDB | | Elaidoylamide | HMDB | | ELD | HMDB | | Kemamide O | HMDB | | Octadecene amide | HMDB | | Petrac slip-eze | HMDB | | Polydis TR 121 | HMDB | | Slip-eze | HMDB | | Tocris-0878 | HMDB | | trans-9,10-Octadecenoamide | HMDB | | Unislip 1759 | HMDB | | Oleylamide, (e)-isomer | HMDB |
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| Chemical Formula | C18H35NO |
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| Average Mass | 281.4766 Da |
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| Monoisotopic Mass | 281.27186 Da |
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| IUPAC Name | (9Z)-octadec-9-enamide |
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| Traditional Name | oleamide |
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| CAS Registry Number | Not Available |
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| SMILES | CCCCCCCC\C=C/CCCCCCCC(N)=O |
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| InChI Identifier | InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9- |
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| InChI Key | FATBGEAMYMYZAF-KTKRTIGZSA-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 | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. |
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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 amides |
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| Direct Parent | Fatty amides |
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| Alternative Parents | |
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| Substituents | - Fatty amide
- Primary carboxylic acid amide
- Carboxamide group
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- 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 | - Huitron-Resendiz S, Gombart L, Cravatt BF, Henriksen SJ: Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats. Exp Neurol. 2001 Nov;172(1):235-43. doi: 10.1006/exnr.2001.7792. [PubMed:11681856 ]
- Hiley CR, Hoi PM: Oleamide: a fatty acid amide signaling molecule in the cardiovascular system? Cardiovasc Drug Rev. 2007 Spring;25(1):46-60. doi: 10.1111/j.1527-3466.2007.00004.x. [PubMed:17445087 ]
- Izquierdo-Garcia JL, Naz S, Nin N, Rojas Y, Erazo M, Martinez-Caro L, Garcia A, de Paula M, Fernandez-Segoviano P, Casals C, Esteban A, Ruiz-Cabello J, Barbas C, Lorente JA: A Metabolomic Approach to the Pathogenesis of Ventilator-induced Lung Injury. Anesthesiology. 2014 Mar;120(3):694-702. doi: 10.1097/ALN.0000000000000074. [PubMed:24253045 ]
- LOTUS database [Link]
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