Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 23:20:55 UTC |
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Update Date | 2020-05-21 16:29:07 UTC |
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BMDB ID | BMDB0006254 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Hydroxyretinoic acid |
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Description | 4-Hydroxyretinoic 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. 4-Hydroxyretinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Hydroxyretinoic acid participates in a number of enzymatic reactions, within cattle. In particular, 4-Hydroxyretinoic acid can be biosynthesized from all-trans-retinoic acid; which is catalyzed by the enzyme cytochrome P450 26A1. In addition, 4-Hydroxyretinoic acid can be converted into 4-oxo-retinoic acid; which is mediated by the enzyme cytochrome P450 26A1. In cattle, 4-hydroxyretinoic acid 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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(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid | ChEBI | (2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid | ChEBI | (7E,9E,11E,13E)-4-Hydroxyretinoic acid | ChEBI | 4-Hydroxy-(7E,9E,11E,13E)-retinoic acid | ChEBI | 4-Hydroxy-all-trans-retinoic acid | ChEBI | (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate | Generator | (2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoate | Generator | (7E,9E,11E,13E)-4-Hydroxyretinoate | Generator | 4-Hydroxy-(7E,9E,11E,13E)-retinoate | Generator | 4-Hydroxy-all-trans-retinoate | Generator | 4-Hydroxyretinoate | Generator | 4-Hydroxy-13-cis-retinoate | HMDB | 4-Hydroxy-13-cis-retinoic acid | HMDB, MeSH | 4-Hydroxy-retinoate | HMDB | 4-Hydroxy-retinoic acid | HMDB | 4-OH-Retinoate | HMDB | 4-OH-Retinoic acid | HMDB | all-trans-4-Hydroxyretinoate | HMDB | all-trans-4-Hydroxyretinoic acid | HMDB | rac-4-Hydroxy-all-trans-retinoate | HMDB | rac-4-Hydroxy-all-trans-retinoic acid | HMDB | 4-Hydroxy-13-retinoic acid | MeSH, HMDB | 4-Hydroxyretinoic acid, (13-cis)-isomer | MeSH, HMDB |
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Chemical Formula | C20H28O3 |
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Average Molecular Weight | 316.4345 |
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Monoisotopic Molecular Weight | 316.203844762 |
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IUPAC Name | (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid |
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Traditional Name | 4-hydroxyretinoic acid |
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CAS Registry Number | 66592-72-1 |
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SMILES | C\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O |
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InChI Identifier | InChI=1S/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+ |
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InChI Key | KGUMXGDKXYTTEY-FRCNGJHJSA-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
- Hydroxy fatty acid
- Methyl-branched fatty acid
- Unsaturated fatty acid
- Fatty acyl
- Fatty acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Alcohol
- 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
- 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 | splash10-0k92-1093000000-7f88a5d83645fa2a79e9 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0092-5008900000-f94c9a4b723e495dbc22 | 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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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kb-0292000000-4d5a6c9335a4fa5db05e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0zg1-0590000000-0b50fabd74e810e935c0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pba-3920000000-8958845f26cb19e0194b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0089000000-cdb17ed778c9480eb63e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0gi1-0094000000-b75b3689212cfa9472cb | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-4390000000-5614482c4d64bf67afaf | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000t-0291000000-7a67cccc8b73d68d76e3 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f8i-0490000000-891d9992953ed919a7c3 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000l-5920000000-8f663f06367ea569c02e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0096000000-123a0c931fe8f0c0d401 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0190000000-3eec1ef4274b19e5f537 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-016r-4910000000-9e73ac1032f900dd901d | View in MoNA |
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