Record Information |
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Version | 2.0 |
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Created at | 2022-09-11 07:36:52 UTC |
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Updated at | 2022-09-11 07:36:52 UTC |
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NP-MRD ID | NP0311549 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | stearolic acid |
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Description | Stearolic acid, also known as 9-stearolate or 9-ODA, 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. stearolic acid is found in Jodina rhombifolia, Panax ginseng and Paramacrolobium coeruleum. stearolic acid was first documented in 2013 (PMID: 24062307). Based on a literature review a small amount of articles have been published on stearolic acid (PMID: 29625270) (PMID: 25264284) (PMID: 23870929) (PMID: 23797276). |
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Structure | InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-8,11-17H2,1H3,(H,19,20) |
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Synonyms | Value | Source |
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9-Octadecynoic acid | ChEBI | 9-ODA | ChEBI | 9-ODYA | ChEBI | 9-Stearolic acid | ChEBI | 9a-18:1 | ChEBI | Delta(9)-Octadecynoic acid | ChEBI | Octadec-9-insaeure | ChEBI | Stearolsaeure | ChEBI | Octadec-9-ynoic acid | Kegg | 9-Octadecynoate | Generator | 9-Stearolate | Generator | delta(9)-Octadecynoate | Generator | Δ(9)-octadecynoate | Generator | Δ(9)-octadecynoic acid | Generator | Octadec-9-ynoate | Generator | Stearolate | Generator |
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Chemical Formula | C18H32O2 |
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Average Mass | 280.4520 Da |
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Monoisotopic Mass | 280.24023 Da |
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IUPAC Name | octadec-9-ynoic acid |
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Traditional Name | stearolic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCC#CCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-8,11-17H2,1H3,(H,19,20) |
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InChI Key | RGTIBVZDHOMOKC-UHFFFAOYSA-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, 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 |
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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
- Unsaturated fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen 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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External Links |
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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 | C00001293 |
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Chemspider ID | 61475 |
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KEGG Compound ID | C08459 |
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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 | 68167 |
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PDB ID | Not Available |
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ChEBI ID | 28801 |
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Good Scents ID | Not Available |
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References |
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General References | - Londero VS, da Costa-Silva TA, Gomes KS, Ferreira DD, Mesquita JT, Tempone AG, Young MCM, Jerz G, Lago JHG: Acetylenic fatty acids from Porcelia macrocarpa (Annonaceae) against trypomastigotes of Trypanosoma cruzi: Effect of octadec-9-ynoic acid in plasma membrane electric potential. Bioorg Chem. 2018 Aug;78:307-311. doi: 10.1016/j.bioorg.2018.03.025. Epub 2018 Mar 30. [PubMed:29625270 ]
- Baba T, Takai K, Takagi T, Kanamori T: Effect of the fluorination degree of hydrophobic chains on the monolayer behavior of unsaturated diacylphosphatidylcholines bearing partially fluorinated 9-octadecynoyl (stearoloyl) groups at the air-water interface. Colloids Surf B Biointerfaces. 2014 Nov 1;123:246-53. doi: 10.1016/j.colsurfb.2014.09.023. Epub 2014 Sep 22. [PubMed:25264284 ]
- Okada S, Zhou XR, Damcevski K, Gibb N, Wood C, Hamberg M, Haritos VS: Diversity of Delta12 fatty acid desaturases in santalaceae and their role in production of seed oil acetylenic fatty acids. J Biol Chem. 2013 Nov 8;288(45):32405-32413. doi: 10.1074/jbc.M113.511931. Epub 2013 Sep 23. [PubMed:24062307 ]
- Wang X, Zhang M, Zhao Y, Wang H, Liu T, Xin Z: Pentadecyl ferulate, a potent antioxidant and antiproliferative agent from the halophyte Salicornia herbacea. Food Chem. 2013 Dec 1;141(3):2066-74. doi: 10.1016/j.foodchem.2013.05.043. Epub 2013 May 21. [PubMed:23870929 ]
- Alloatti A, Tripodi KE, Uttaro AD: Synergistic effect of inhibitors of fatty acid desaturases on Trypanosoma parasites. Parasitol Res. 2013 Jun 25. doi: 10.1007/s00436-013-3508-y. [PubMed:23797276 ]
- LOTUS database [Link]
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