Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-10-30 10:32:48 UTC |
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Update Date | 2022-03-07 03:17:34 UTC |
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HMDB ID | HMDB0059633 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (9S,10S)-9,10-dihydroxyoctadecanoate |
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Description | (9S,10S)-9,10-dihydroxyoctadecanoate, also known as (S,S)-9,10-dihydroxystearic acid or (9S,10S)-dihydroxystearate, 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 (9S,10S)-9,10-dihydroxyoctadecanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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Structure | [H][C@](O)(CCCCCCCC)[C@@]([H])(O)CCCCCCCC(O)=O InChI=1S/C18H36O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h16-17,19-20H,2-15H2,1H3,(H,21,22)/t16-,17-/m0/s1 |
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Synonyms | Value | Source |
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(9S,10S)-9,10-Dihydroxystearic acid | ChEBI | (9S,10S)-Dihydroxdyoctadecanoic acid | ChEBI | (9S,10S)-Dihydroxystearic acid | ChEBI | (S,S)-9,10-Dihydroxystearic acid | ChEBI | (9S,10S)-9,10-Dihydroxystearate | Generator | (9S,10S)-Dihydroxdyoctadecanoate | Generator | (9S,10S)-Dihydroxystearate | Generator | (S,S)-9,10-Dihydroxystearate | Generator | (9S,10S)-9,10-Dihydroxyoctadecanoic acid | Generator | (9S,10S)-9,10-Dihydroxyoctadecanoate | Generator |
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Chemical Formula | C18H36O4 |
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Average Molecular Weight | 316.476 |
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Monoisotopic Molecular Weight | 316.26135964 |
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IUPAC Name | (9S,10S)-9,10-dihydroxyoctadecanoic acid |
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Traditional Name | (9S,10S)-dihydroxystearic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](O)(CCCCCCCC)[C@@]([H])(O)CCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C18H36O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h16-17,19-20H,2-15H2,1H3,(H,21,22)/t16-,17-/m0/s1 |
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InChI Key | VACHUYIREGFMSP-IRXDYDNUSA-N |
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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
- Secondary alcohol
- 1,2-diol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(9S,10S)-9,10-dihydroxyoctadecanoate,1TMS,isomer #1 | CCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CCCCCCCC(=O)O | 2516.7 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,1TMS,isomer #2 | CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C | 2519.0 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,1TMS,isomer #3 | CCCCCCCC[C@H](O)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C | 2558.1 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,2TMS,isomer #1 | CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C | 2555.5 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,2TMS,isomer #2 | CCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C | 2572.4 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,2TMS,isomer #3 | CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2574.3 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,3TMS,isomer #1 | CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2621.1 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,1TBDMS,isomer #1 | CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCCCCCC(=O)O | 2760.3 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,1TBDMS,isomer #2 | CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2761.1 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,1TBDMS,isomer #3 | CCCCCCCC[C@H](O)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C | 2812.0 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,2TBDMS,isomer #1 | CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3072.0 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,2TBDMS,isomer #2 | CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C | 3078.0 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,2TBDMS,isomer #3 | CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3077.4 | Semi standard non polar | 33892256 | (9S,10S)-9,10-dihydroxyoctadecanoate,3TBDMS,isomer #1 | CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3360.4 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dm-7920000000-5d5f4cd379839da63600 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate GC-MS (3 TMS) - 70eV, Positive | splash10-014i-9112210000-4c89c9fa67d4344f8ea6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 10V, Positive-QTOF | splash10-0002-0192000000-8aab6406655a84cf775d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 20V, Positive-QTOF | splash10-03ea-5950000000-3a7ee5e5bd1701383cf4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 40V, Positive-QTOF | splash10-052f-9310000000-a53182b68f011f3ad319 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 10V, Negative-QTOF | splash10-014i-0059000000-64ea459047babba3821e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 20V, Negative-QTOF | splash10-00r5-0952000000-7ec7f5e455fb1fbaf90a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 40V, Negative-QTOF | splash10-0a4l-6900000000-5436f5e2916990719cfa | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 10V, Positive-QTOF | splash10-000t-0191000000-e4d08971240d043896d7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 20V, Positive-QTOF | splash10-05u2-9880000000-5070a163721cdae8d9f9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 40V, Positive-QTOF | splash10-0a59-9200000000-cf5b50915d51f39d1443 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 10V, Negative-QTOF | splash10-014i-0029000000-2b51d6a4632977033c10 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 20V, Negative-QTOF | splash10-014j-0797000000-ae27ab91a61b2dd99b59 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 40V, Negative-QTOF | splash10-00bd-4951000000-8528023e01bfc8607628 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | C15988 |
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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 | 12235230 |
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PDB ID | Not Available |
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ChEBI ID | 49254 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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