Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:44:40 UTC |
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Update Date | 2020-05-21 16:29:06 UTC |
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BMDB ID | BMDB0001358 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Retinal |
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Description | 13-cis-13-cis-13-cis-retinal, also known as 13Z-13-cis-retinal or 13-cis-retinal, 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. Thus, 13-cis-13-cis-retinal is considered to be an isoprenoid lipid molecule. 13-cis-13-cis-13-cis-retinal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 13-cis-13-cis-13-cis-retinal exists in all living organisms, ranging from bacteria to humans. In cattle, 13-cis-13-cis-retinal is involved in the metabolic pathway called the retinol metabolism pathway. |
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Structure | |
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Synonyms | Value | Source |
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all-trans-Retinaldehyde | ChEBI | all-trans-Retinene | ChEBI | all-trans-Vitamin a aldehyde | ChEBI | Retinaldehyde | ChEBI | Retinene | ChEBI | Vitamin a aldehyde | ChEBI | all-trans-Retinal | Kegg | Aldehyde, vitamin a | HMDB | Axerophthal | HMDB | 11 cis Retinal | HMDB | 11-cis-Retinal | HMDB | 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal | HMDB | all-e-Retinal | HMDB | all-epsilon-Retinal | HMDB | alpha-Retinene | HMDB | e-Retinal | HMDB | epsilon-Retinal | HMDB | Retinene 1 | HMDB | trans-Retinal | HMDB | trans-Vitamin a aldehyde | HMDB | Vitamin a1 aldehyde | 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 | (2E,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 | retinaldehyde |
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CAS Registry Number | 116-31-4 |
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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-OVSJKPMPSA-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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Status | Expected but not Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cell membrane
- Cytoplasm
- Membrane
- Myelin sheath
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 63 °C | 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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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-014i-2290000000-df9d2aa7545cc60a54f9 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-014i-9700000000-c2e22000dfae0765c367 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-03g0-0950000000-bccf87de037f98873f41 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-01t9-1910000000-5fe7643c395769c68286 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-014i-9700000000-fca532f917595376d653 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0490000000-f543f08fbaf94a2e3f8e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-3940000000-74f087cc812b3715e7ac | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fri-9830000000-72a5d01c6181340ad986 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0090000000-bad35938b77f181c29b9 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0090000000-1aadad0770df07f98436 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00ko-4690000000-f624d342f88456375b9c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00n3-1960000000-43f8c66f164764c37361 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0609-3920000000-dbeab0a82b306761cf6a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-7900000000-d2bb7c1aeeb87d8833d2 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a59-0090000000-2ec2f8f314943441fa15 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0pb9-0190000000-312cebb17ccd0189ab4d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-1590000000-b2551eac481c0c930a4d | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | - Cell membrane
- Cytoplasm
- Membrane
- Myelin sheath
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Biospecimen Locations | - Adrenal Cortex
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Lung
- Neuron
- Pancreas
- Placenta
- Platelet
- Skeletal Muscle
- Spleen
- Testis
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Pathways | |
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Normal Concentrations |
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Adrenal Cortex | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Lung | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Pancreas | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Skeletal Muscle | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Testis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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HMDB ID | HMDB0001358 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022576 |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | C00376 |
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BioCyc ID | RETINAL |
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BiGG ID | Not Available |
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Wikipedia Link | Retinal |
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METLIN ID | Not Available |
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PubChem Compound | 638015 |
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PDB ID | Not Available |
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ChEBI ID | 17898 |
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References |
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Synthesis Reference | Duhamel, Lucette; Duhamel, Pierre; Lecouve, Jean Pierre. A new synthesis of retinals. Journal of Chemical Research, Synopses (1986), (1), 34-5. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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