Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-05-22 15:12:28 UTC |
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Update Date | 2022-03-07 02:49:17 UTC |
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HMDB ID | HMDB0003039 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Isoacitretin |
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Description | Isoacitretin, also known as 13-cis-acitretin or soriatane, 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. Based on a literature review a significant number of articles have been published on Isoacitretin. |
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Structure | COC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C/C(O)=O)C(C)=C1 InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12- |
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Synonyms | Value | Source |
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13-cis-Acitretin | HMDB | 13-cis-Etretin | HMDB | Soriatane | HMDB | Acitretin | HMDB | Acitretin andreu brand | HMDB | Acitretin roche brand | HMDB | Acitretin, (Z,e,e,e)-isomer | HMDB | Andreu brand OF acitretin | HMDB | Etretin | HMDB | Hoffmann la roche brand OF acitretin | HMDB | Hoffmann-la roche brand OF acitretin | HMDB | Isoetretin | HMDB | Neotigason | HMDB | Roche brand OF acitretin | HMDB | (2Z,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid | HMDB | Isoacitretin | MeSH |
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Chemical Formula | C21H26O3 |
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Average Molecular Weight | 326.4293 |
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Monoisotopic Molecular Weight | 326.188194698 |
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IUPAC Name | (2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid |
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Traditional Name | acetretin |
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CAS Registry Number | 69427-46-9 |
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SMILES | COC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C/C(O)=O)C(C)=C1 |
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InChI Identifier | InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12- |
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InChI Key | IHUNBGSDBOWDMA-UGOGCBOOSA-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
- Retinoid skeleton
- Sesquiterpenoid
- Cyclofarsesane sesquiterpenoid
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Medium-chain fatty acid
- Styrene
- Alkyl aryl ether
- Branched fatty acid
- Methyl-branched fatty acid
- Monocyclic benzene moiety
- Fatty acyl
- Fatty acid
- Benzenoid
- Unsaturated fatty acid
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid
- Carboxylic acid derivative
- Carbonyl group
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic 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 | 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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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 - Isoacitretin GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-1279000000-d74bbc0348cfdb3b3732 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isoacitretin GC-MS (1 TMS) - 70eV, Positive | splash10-001i-4139000000-85e857f30a345651bb66 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Isoacitretin 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Isoacitretin LC-ESI-qTof , Positive-QTOF | splash10-01t9-0592000000-92a48c620c961fdb430f | 2018-05-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Isoacitretin , positive-QTOF | splash10-056r-1943000000-77c18bcac662a9f6bdcb | 2018-05-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Isoacitretin , positive-QTOF | splash10-056r-2942000000-57cdf186555912258599 | 2018-05-25 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 10V, Positive-QTOF | splash10-0a4i-0369000000-c76928c945feff099218 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 20V, Positive-QTOF | splash10-0aor-0970000000-83c7baa1aeda7da5a2cb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 40V, Positive-QTOF | splash10-0pvi-4910000000-b657ca2b064b9ff56256 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 10V, Negative-QTOF | splash10-0059-0049000000-4a4ee208619c94b4e2c9 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 20V, Negative-QTOF | splash10-057i-0079000000-35044b92edd7238b81e3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 40V, Negative-QTOF | splash10-066u-2291000000-5bb79aadc2928c46ff88 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 10V, Negative-QTOF | splash10-001j-0092000000-da6b1640ed88e8dd0629 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 20V, Negative-QTOF | splash10-017j-1291000000-8d03b8e6cfa817060924 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 40V, Negative-QTOF | splash10-00dj-1494000000-45aa9916567486569a90 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 10V, Positive-QTOF | splash10-0ke9-0395000000-2d28d3c86a8a16a5adac | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 20V, Positive-QTOF | splash10-03di-0940000000-2f4d9396336fd697861e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Isoacitretin 40V, Positive-QTOF | splash10-00tf-1900000000-f5a87d3a7b17af3487e6 | 2021-09-23 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023099 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4942363 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 621 |
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PubChem Compound | 6437841 |
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PDB ID | Not Available |
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ChEBI ID | 50174 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Mestres Quadreny, Ramon; Tortajada Lopez, Desamparados; Arrell Piquer, Maria Jose; Parra Alvarez, Margarita; Gil Grau, Salvador; Cetta Builelo, Luisa; Simo Planells, Ana. Process for the preparation of aromatic retinoic acids [e.g., etretin] and their derivatives. Span. (1992), 14 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Al-Mallah NR, Bun H, Coassolo P, Aubert C, Cano JP: Determination of the aromatic retinoids (etretin and isoetretin) in biological fluids by high-performance liquid chromatography. J Chromatogr. 1987 Oct 9;421(1):177-86. [PubMed:2963014 ]
- Vane FM, Bugge JL, Rodriguez LC: Identification of etretinate metabolites in human blood. Drug Metab Dispos. 1989 May-Jun;17(3):280-5. [PubMed:2568909 ]
- Fayer BE, Huselton CA, Garland WA, Liberato DJ: Quantification of acitretin in human plasma by microbore liquid chromatography-negative chemical ionization mass spectrometry. J Chromatogr. 1991 Jul 17;568(1):135-44. [PubMed:1837553 ]
- Vane FM, Bugge CJ, Rodriguez LC: Identification of etretinate metabolites in human bile. Drug Metab Dispos. 1989 May-Jun;17(3):275-9. [PubMed:2568908 ]
- De Leenheer AP, Lambert WE, De Bersaques JP, Kint AH: High-performance liquid chromatographic determination of etretinate and all-trans- and 13-cis-acitretin in human plasma. J Chromatogr. 1990 Feb 2;500:637-42. [PubMed:2139439 ]
- Larsen FG, Vahlquist C, Andersson E, Torma H, Kragballe K, Vahlquist A: Oral acitretin in psoriasis: drug and vitamin A concentrations in plasma, skin and adipose tissue. Acta Derm Venereol. 1992;72(2):84-8. [PubMed:1350412 ]
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