| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:54:42 UTC |
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| Update Date | 2020-05-20 23:11:16 UTC |
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| BMDB ID | BMDB0002369 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 9-cis-Retinoic acid |
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| Description | 9-cis-Retinoic acid, also known as 9-cis-retinoic acid or 9-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. 9-cis-Retinoic acid is a drug which is used for topical treatment of cutaneous lesions in patients with aids-related kaposi's sarcoma. 9-cis-Retinoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 9-cis-Retinoic acid participates in a number of enzymatic reactions, within cattle. In particular, 9-cis-Retinoic acid can be biosynthesized from 9-cis-retinal; which is mediated by the enzyme retinal dehydrogenase 1. In addition, 9-cis-Retinoic acid can be biosynthesized from 9-cis-retinal through its interaction with the enzyme retinal dehydrogenase 2. In cattle, 9-cis-retinoic acid is involved in the metabolic pathway called the retinol metabolism pathway. 9-cis-Retinoic acid is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid | ChEBI | | (7E,9Z,11E,13E)-Retinoic acid | ChEBI | | 9(Z)-Retinoic acid | ChEBI | | 9-cis-Tretinoin | ChEBI | | Alitretinoin | ChEBI | | Alitretinoina | ChEBI | | Alitretinoine | ChEBI | | Alitretinoinum | ChEBI | | Panretin | ChEBI | | Panretyn | ChEBI | | (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate | Generator | | (7E,9Z,11E,13E)-Retinoate | Generator | | 9(Z)-Retinoate | Generator | | 9-cis-Retinoate | Generator | | 9 cis Retinoic acid | MeSH | | 9CRA compound | MeSH | | Toctino | MeSH | | 15-apo-beta-Caroten-15-Oate | HMDB | | 15-apo-beta-Caroten-15-Oic acid | HMDB | | 9-Retinoate | HMDB | | 9-Retinoic acid | HMDB | | Aberel | HMDB | | Aberela | HMDB | | Airol | HMDB | | Aknoten | HMDB | | all-trans- Vitamin a1 acid | HMDB | | all-trans-b-Retinoate | HMDB | | all-trans-b-Retinoic acid | HMDB | | all-trans-beta-Retinoate | HMDB | | all-trans-beta-Retinoic acid | HMDB | | all-trans-Vitamin a acid | HMDB | | alpha-Vitaminsyre | HMDB | | Atragen | HMDB | | Avita | HMDB | | Avitoin | HMDB | | b-Retinoate | HMDB | | b-Retinoic acid | HMDB | | beta-Retinoate | HMDB | | beta-Retinoic acid | HMDB | | Dermairol | HMDB | | Effederm | HMDB | | Epi-aberel | HMDB | | Eudyna | HMDB | | Isotretinoin retinoate | HMDB | | Isotretinoin retinoic acid | HMDB | | Panretin gel | HMDB | | Panrexin | HMDB | | Renova | HMDB | | Retacnyl | HMDB | | Retin a | HMDB | | Retin-a | HMDB | | Retin-a micro | HMDB | | Retinoate | HMDB | | Retinoic acid | HMDB | | Retinova | HMDB | | trans-Retinoate | HMDB | | trans-Retinoic acid | HMDB | | trans-Vitamin a acid | HMDB | | Tretinoin | HMDB | | Tretinoin/all-trans retinoate | HMDB | | Tretinoin/all-trans retinoic acid | HMDB | | Tretinon | HMDB | | Vesanoid | HMDB | | Vesnaroid | HMDB |
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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 | (2E,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 | alitretinoin |
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| CAS Registry Number | 5300-03-8 |
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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-ZVCIMWCZSA-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 | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Membrane
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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-2190000000-86aaab132a5b092ebf10 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0a4i-5139000000-29caedb85908ca2b99f4 | 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 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, 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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| 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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