Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-07-25 00:09:00 UTC |
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Update Date | 2022-03-07 02:51:27 UTC |
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HMDB ID | HMDB0012874 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 9,13-cis-Retinoic acid |
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Description | 9,13-cis-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. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). |
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Structure | C\C(\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C(\C)=C/C(O)=O 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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Synonyms | Value | Source |
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9,13-cis-Retinoate | Generator | 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-(2E,4Z,6E,8Z)-nonatetraen-1-Oate | HMDB | 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-(2E,4Z,6E,8Z)-nonatetraen-1-Oic acid | HMDB | 9,13-cis-Retinoic acid | HMDB, Generator | 9,13-cis-Retinoic acid anion | HMDB | 9,13-cis-Vitamin-a-acid | HMDB | 9,13-cis-Vitamin-alpha-acid | HMDB | 9,13-Di-cis-ra | HMDB | 9-cis,13-cis-Retinoate | HMDB | 9-cis,13-cis-Retinoic acid | HMDB | DcVA | HMDB | 9,13-Retinoic acid | MeSH, HMDB | 9,13-Di-cis-retinoate | Generator |
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Chemical Formula | C20H28O2 |
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Average Molecular Weight | 300.4351 |
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Monoisotopic Molecular Weight | 300.20893014 |
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IUPAC Name | (2Z,4E,6Z,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 | 9,13-di-cis-retinoic acid |
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CAS Registry Number | 5352-74-9 |
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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-CDMOMSTLSA-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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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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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 | 181 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 6.30 | HANSCH,C ET AL. (1995) |
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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 IndicesUnderivatizedDerivatized |
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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 - 9,13-cis-Retinoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-000i-2190000000-86aaab132a5b092ebf10 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 9,13-cis-Retinoic acid GC-MS (1 TMS) - 70eV, Positive | splash10-0a4i-5139000000-29caedb85908ca2b99f4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 9,13-cis-Retinoic 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 |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 10V, Positive-QTOF | splash10-001i-0392000000-2208a551cdad109fbac3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 20V, Positive-QTOF | splash10-053i-1940000000-ace2a3043044e52c8ad3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 40V, Positive-QTOF | splash10-05nr-7900000000-1ee1af1ccb7ebac135f0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 10V, Negative-QTOF | splash10-052b-0090000000-ca9b2a996cc511290cb5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 20V, Negative-QTOF | splash10-0a5a-0090000000-4cb06190f795e5879208 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 40V, Negative-QTOF | splash10-053i-3590000000-09c02aaba9f83079f9c2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 10V, Positive-QTOF | splash10-0zir-0973000000-3040e9e4a1a5448efbcb | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 20V, Positive-QTOF | splash10-060c-1950000000-f3b9c9b378f60b8c49a9 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 40V, Positive-QTOF | splash10-0ar3-5910000000-de22eb65f274483f3f98 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 10V, Negative-QTOF | splash10-052b-0090000000-5f942e3b870e7bd0121b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 20V, Negative-QTOF | splash10-0a4i-0190000000-22b445382d3977280045 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9,13-cis-Retinoic acid 40V, Negative-QTOF | splash10-016r-4900000000-0005b37f6d54a42a84f6 | 2021-09-24 | Wishart Lab | View Spectrum |
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