Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-22 17:57:51 UTC |
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Update Date | 2022-03-07 02:49:30 UTC |
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HMDB ID | HMDB0006220 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 13-cis-Retinal |
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Description | 13-cis-Retinal is a naturally occurring retinoid. Retinoids are vitamin A analogs that have profound biological activities. Several retinoids have been reported to have antiinflammatory activity in certain animal models of arthritis, such as adjuvant-induced and streptococcal cell wall-induced arthritis in rats. Some retinoids also have been shown to possess antiinftammatory activity in man by their ability to modulate inflammatory diseases of the skin. It has been reported, for example, that retinoid treatment can inhibit neutrophil accumulation in cutaneous disorders such as psoriasis. (PMID:2123476 ). |
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Structure | C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13- |
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Synonyms | Value | Source |
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(13cis)-Retinal | ChEBI | (2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal | ChEBI | 13-cis-Retinaldehyde | ChEBI | RETINAL | ChEBI | 13Z-Retinal | HMDB | cis-13-Retinal | HMDB | Neoretinene a | HMDB | Neovitamin a aldehyde | HMDB | 13-cis-Retinal | MeSH, HMDB |
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Chemical Formula | C20H28O |
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Average Molecular Weight | 284.4357 |
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Monoisotopic Molecular Weight | 284.214015518 |
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IUPAC Name | (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal |
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Traditional Name | 13-cis retinal |
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CAS Registry Number | 472-86-6 |
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SMILES | C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O |
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InChI Identifier | InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13- |
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InChI Key | NCYCYZXNIZJOKI-HWCYFHEPSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Retinoids |
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Direct Parent | Retinoids |
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Alternative Parents | |
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Substituents | - Retinoid skeleton
- Diterpenoid
- Enal
- Alpha,beta-unsaturated aldehyde
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aldehyde
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic 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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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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 - 13-cis-Retinal GC-MS (Non-derivatized) - 70eV, Positive | splash10-014i-2290000000-df9d2aa7545cc60a54f9 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 13-cis-Retinal GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 13-cis-Retinal 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 - 13-cis-Retinal 10V, Positive-QTOF | splash10-000i-0490000000-f543f08fbaf94a2e3f8e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 20V, Positive-QTOF | splash10-000i-3940000000-83ca23fc3e32f84b7d9b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 40V, Positive-QTOF | splash10-0fri-9720000000-b077361f8a6c0a0a6c99 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 10V, Negative-QTOF | splash10-001i-0090000000-bad35938b77f181c29b9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 20V, Negative-QTOF | splash10-001i-0090000000-1aadad0770df07f98436 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 40V, Negative-QTOF | splash10-00ko-4690000000-f624d342f88456375b9c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 10V, Negative-QTOF | splash10-0a59-0090000000-2ec2f8f314943441fa15 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 20V, Negative-QTOF | splash10-0pb9-0190000000-312cebb17ccd0189ab4d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 40V, Negative-QTOF | splash10-000i-1590000000-b2551eac481c0c930a4d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 10V, Positive-QTOF | splash10-00n3-1960000000-43f8c66f164764c37361 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 20V, Positive-QTOF | splash10-0609-3920000000-dbeab0a82b306761cf6a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 13-cis-Retinal 40V, Positive-QTOF | splash10-052f-7900000000-d2bb7c1aeeb87d8833d2 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | 2018-05-25 | Wishart Lab | View Spectrum |
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