Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2017-03-23 04:25:48 UTC |
---|
Update Date | 2022-03-07 03:17:56 UTC |
---|
HMDB ID | HMDB0062566 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | 3-hydroxyicosanoic Acid |
---|
Description | 3-hydroxyicosanoic Acid, also known as 3-hydroxyeicosanoate or 3-hydroxyarachidic acid, 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. Thus, 3-hydroxyicosanoic Acid is considered to be a fatty acid lipid molecule. 3-hydroxyicosanoic Acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
---|
Structure | CCCCCCCCCCCCCCCCCC(O)CC(O)=O InChI=1S/C20H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(21)18-20(22)23/h19,21H,2-18H2,1H3,(H,22,23) |
---|
Synonyms | Value | Source |
---|
3-Hydroxyarachidic acid | ChEBI | 3-Hydroxyeicosanoic acid | ChEBI | beta-Hydroxyachidic acid | ChEBI | beta-Hydroxyeicosanoic acid | ChEBI | beta-Hydroxyicosanoic acid | ChEBI | 3-Hydroxyarachidate | Generator | 3-Hydroxyeicosanoate | Generator | b-Hydroxyachidate | Generator | b-Hydroxyachidic acid | Generator | beta-Hydroxyachidate | Generator | Β-hydroxyachidate | Generator | Β-hydroxyachidic acid | Generator | b-Hydroxyeicosanoate | Generator | b-Hydroxyeicosanoic acid | Generator | beta-Hydroxyeicosanoate | Generator | Β-hydroxyeicosanoate | Generator | Β-hydroxyeicosanoic acid | Generator | b-Hydroxyicosanoate | Generator | b-Hydroxyicosanoic acid | Generator | beta-Hydroxyicosanoate | Generator | Β-hydroxyicosanoate | Generator | Β-hydroxyicosanoic acid | Generator | 3-Hydroxyicosanoate | Generator |
|
---|
Chemical Formula | C20H40O3 |
---|
Average Molecular Weight | 328.537 |
---|
Monoisotopic Molecular Weight | 328.297745148 |
---|
IUPAC Name | 3-hydroxyicosanoic acid |
---|
Traditional Name | 3-hydroxyeicosanoic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | CCCCCCCCCCCCCCCCCC(O)CC(O)=O |
---|
InChI Identifier | InChI=1S/C20H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(21)18-20(22)23/h19,21H,2-18H2,1H3,(H,22,23) |
---|
InChI Key | XXKHCFPQYSMGCI-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty acids and conjugates |
---|
Direct Parent | Long-chain fatty acids |
---|
Alternative Parents | |
---|
Substituents | - Long-chain fatty acid
- Hydroxy fatty acid
- Beta-hydroxy acid
- Hydroxy acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | Not Available |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.00049 g/l | ALOGPS | LogP | 7.69 | ALOGPS |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
3-hydroxyicosanoic Acid,1TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C | 2587.6 | Semi standard non polar | 33892256 | 3-hydroxyicosanoic Acid,1TMS,isomer #2 | CCCCCCCCCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C | 2592.2 | Semi standard non polar | 33892256 | 3-hydroxyicosanoic Acid,2TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2613.7 | Semi standard non polar | 33892256 | 3-hydroxyicosanoic Acid,1TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(CC(=O)O)O[Si](C)(C)C(C)(C)C | 2845.9 | Semi standard non polar | 33892256 | 3-hydroxyicosanoic Acid,1TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCC(O)CC(=O)O[Si](C)(C)C(C)(C)C | 2846.9 | Semi standard non polar | 33892256 | 3-hydroxyicosanoic Acid,2TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3104.0 | Semi standard non polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - 3-hydroxyicosanoic Acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-8591000000-7c0e3bce2074cd9f44a0 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-hydroxyicosanoic Acid GC-MS (2 TMS) - 70eV, Positive | splash10-0adl-9323100000-b4f0900b618498979ae5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-hydroxyicosanoic Acid 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 |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 10V, Positive-QTOF | splash10-03di-0059000000-e936c41a541b1540339d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 20V, Positive-QTOF | splash10-02vl-1193000000-5fa84dc3a4c4f13c217a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 40V, Positive-QTOF | splash10-052o-6690000000-08e36015aa3a28f49e5c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 10V, Negative-QTOF | splash10-056r-0039000000-0af44605508babc94390 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 20V, Negative-QTOF | splash10-0api-3097000000-4b46f0aef956a1b66e60 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 40V, Negative-QTOF | splash10-0aou-9060000000-62e5ae5b33515cbd8fcc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 10V, Positive-QTOF | splash10-004i-2039000000-60db8ad7748a61608b91 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 20V, Positive-QTOF | splash10-0c2c-9434000000-b55c6091b4d8a27d70d2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 40V, Positive-QTOF | splash10-0a4l-9000000000-71382d945a6f62452728 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 10V, Negative-QTOF | splash10-056r-7009000000-2d03ff18c9997b38b2d8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 20V, Negative-QTOF | splash10-0a4i-9000000000-989d9940c0b7c715d5b3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-hydroxyicosanoic Acid 40V, Negative-QTOF | splash10-0006-9000000000-1dbaabbf4e0297e1818a | 2021-09-22 | Wishart Lab | View Spectrum |
|
---|
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.
|
---|