Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:48:09 UTC |
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Update Date | 2020-05-21 16:29:27 UTC |
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BMDB ID | BMDB0001852 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Retinoic acid |
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Description | all-trans-All-trans-all-all-trans-retinoic acid, also known as all-all-trans-retinoic acid or all-trans-retinoic acid, 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. all-trans-All-trans-all-all-trans-retinoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. all-trans-All-trans-all-all-trans-retinoic acid participates in a number of enzymatic reactions, within cattle. In particular, all-trans-All-trans-all-all-trans-retinoic acid can be biosynthesized from vitamin a through the action of the enzyme retinal dehydrogenase 1. In addition, all-trans-All-trans-all-all-trans-retinoic acid can be biosynthesized from vitamin a; which is mediated by the enzyme retinal dehydrogenase 2. In cattle, all-trans-all-all-trans-retinoic acid is involved in the metabolic pathway called the retinol metabolism pathway. all-trans-All-trans-all-all-trans-retinoic acid is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid | ChEBI | 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl) | ChEBI | AGN 100335 | ChEBI | all-(e)-Retinoic acid | ChEBI | all-trans-beta-Retinoic acid | ChEBI | all-trans-Tretinoin | ChEBI | all-trans-Vitamin a acid | ChEBI | all-trans-Vitamin a1 acid | ChEBI | beta-Retinoic acid | ChEBI | Eudyna | ChEBI | Renova | ChEBI | Retin-a | ChEBI | Retinoic acid | ChEBI | Retisol-a | ChEBI | Ro 1-5488 | ChEBI | Solage | ChEBI | Stieva-a | ChEBI | trans-Retinoic acid | ChEBI | Tretin m | ChEBI | Tretinoin | ChEBI | Vesanoid | ChEBI | Vitamin a acid | ChEBI | Vitinoin | ChEBI | all-trans-Retinoate | Kegg | Avita | Kegg | Retin a | Kegg | (all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate | Generator | 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl) | Generator | all-(e)-Retinoate | Generator | all-trans-b-Retinoate | Generator | all-trans-b-Retinoic acid | Generator | all-trans-beta-Retinoate | Generator | all-trans-Β-retinoate | Generator | all-trans-Β-retinoic acid | Generator | b-Retinoate | Generator | b-Retinoic acid | Generator | beta-Retinoate | Generator | Β-retinoate | Generator | Β-retinoic acid | Generator | Retinoate | Generator | trans-Retinoate | Generator | (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate | HMDB | Tretinoin zinc salt | HMDB | trans Retinoic acid | HMDB | Acid, all-trans-retinoic | HMDB | Salt, tretinoin sodium | HMDB | beta all trans Retinoic acid | HMDB | beta-all-trans-Retinoic acid | HMDB | Acid, vitamin a | HMDB | Potassium salt, tretinoin | HMDB | Sodium salt, tretinoin | HMDB | Acid, beta-all-trans-retinoic | HMDB | Tretinoin potassium salt | HMDB | Zinc salt, tretinoin | HMDB | Acid, retinoic | HMDB | Acid, trans-retinoic | HMDB | Salt, tretinoin potassium | HMDB | Salt, tretinoin zinc | HMDB | Tretinoin sodium salt | HMDB | all trans Retinoic acid | HMDB | Retin-a micro | HMDB | Atralin | HMDB | Tretin-X | HMDB | all-trans-Retinoic acid | MeSH |
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Chemical Formula | C20H28O2 |
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Average Molecular Weight | 300.442 |
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Monoisotopic Molecular Weight | 300.208930142 |
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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-tetraenoic acid |
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Traditional Name | tretinoin |
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CAS Registry Number | 302-79-4 |
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SMILES | C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O |
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InChI Identifier | InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+ |
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InChI Key | SHGAZHPCJJPHSC-YCNIQYBTSA-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 | - Retinoic acid
- Diterpenoid
- Retinoid skeleton
- Medium-chain fatty acid
- Branched fatty acid
- Methyl-branched fatty acid
- Fatty acyl
- Unsaturated fatty acid
- Fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- 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 | Not Available |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Membrane
- Myelin sheath
- Nucleus
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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 | 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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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 | splash10-000i-2090000000-db078f48efb8038384f2 | 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 - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-0009000000-12dbd83959268dee6dbf | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-066r-4900000000-31c9262cbbf0bad5b738 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0fsl-9600000000-c6681587f0a9ae7a712e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0mc0-4941000000-401db468e6db7c5bbb5a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0a4i-0090000000-d05c305f987a713dfaa0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0239000000-09da873ecbe1e09a1602 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0090000000-dca272cadb8a3ba3f819 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-016r-9630000000-553ddaf9452713df67ee | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0390000000-241af7f979164ecfbf34 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0mc0-4941000000-05bed4117d9ed953a2ca | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9400000000-3ecfeb7f6c8384d2a0d3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0239000000-2c6852256fcbebe1a2aa | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-00di-0910000000-a1c1aa8b35e78558cd5b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0uei-0494000000-28e6366fdd47e8ba2117 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-2980000000-3e7fc78de83c23830416 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052r-5900000000-ef4d86f8bcf86959f794 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-052b-0090000000-e07ffb4c1e5c63ab1b59 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052b-0090000000-a0a8411213bbd2543243 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-3690000000-97e6a74798dd69c30ad1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0zir-0973000000-3040e9e4a1a5448efbcb | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-060c-1950000000-f3b9c9b378f60b8c49a9 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ar3-5910000000-de22eb65f274483f3f98 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-052b-0090000000-5f942e3b870e7bd0121b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0190000000-22b445382d3977280045 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-016r-4900000000-0005b37f6d54a42a84f6 | 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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