Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2022-03-07 02:51:53 UTC |
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HMDB ID | HMDB0015160 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Amlexanox |
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Description | Amlexanox, also known as aphthasol or solfa, belongs to the class of organic compounds known as chromeno[2,3-b]pyridine-5-ones. Chromeno[2,3-b]pyridine-5-ones are compounds containing a Chromeno[2,3-b]pyridine moiety that carries an oxo group at the 5-position. Amlexanox is a drug which is used as a paste in the mouth to treat aphthous ulcers (canker sores). . Amlexanox is an extremely weak basic (essentially neutral) compound (based on its pKa). A pyridochromene-derived monocarboxylic acid having an amino substituent at the 2-position, an oxo substituent at the 5-position and an isopropyl substituent at the 7-position. |
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Structure | CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1 InChI=1S/C16H14N2O4/c1-7(2)8-3-4-12-9(5-8)13(19)10-6-11(16(20)21)14(17)18-15(10)22-12/h3-7H,1-2H3,(H2,17,18)(H,20,21) |
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Synonyms | Value | Source |
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2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylic acid | ChEBI | Amlexanoxo | ChEBI | Amlexanoxum | ChEBI | Aphthasol | Kegg | Solfa | Kegg | 2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylate | Generator | 2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3b)pyridine-3-carboxylic acid | HMDB | GlaxoSmithKline brand OF amlexanox | HMDB | Amoxanox | HMDB |
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Chemical Formula | C16H14N2O4 |
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Average Molecular Weight | 298.2934 |
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Monoisotopic Molecular Weight | 298.095356946 |
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IUPAC Name | 2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid |
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Traditional Name | aphthasol |
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CAS Registry Number | 68302-57-8 |
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SMILES | CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1 |
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InChI Identifier | InChI=1S/C16H14N2O4/c1-7(2)8-3-4-12-9(5-8)13(19)10-6-11(16(20)21)14(17)18-15(10)22-12/h3-7H,1-2H3,(H2,17,18)(H,20,21) |
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InChI Key | SGRYPYWGNKJSDL-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as chromeno[2,3-b]pyridine-5-ones. Chromeno[2,3-b]pyridine-5-ones are compounds containing a Chromeno[2,3-b]pyridine moiety that carries an oxo group at the 5-position. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzopyrans |
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Sub Class | 1-benzopyrans |
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Direct Parent | Chromeno[2,3-b]pyridine-5-ones |
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Alternative Parents | |
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Substituents | - Chromeno[2,3-b]pyridine-5-one
- Chromenopyridine
- Pyranopyridine
- Pyridine carboxylic acid
- Pyridine carboxylic acid or derivatives
- Aminopyridine
- Pyranone
- Pyran
- Pyridine
- Benzenoid
- Imidolactam
- Heteroaromatic compound
- Vinylogous amide
- Amino acid or derivatives
- Amino acid
- Oxacycle
- Azacycle
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Amine
- Organooxygen compound
- Organonitrogen compound
- Primary amine
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Organic nitrogen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | Not Available |
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Role | Not Available |
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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 | 0.15 g/L | Not Available | LogP | 4.1 | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Amlexanox,1TMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1 | 3090.6 | Semi standard non polar | 33892256 | Amlexanox,1TMS,isomer #2 | CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1 | 3064.7 | Semi standard non polar | 33892256 | Amlexanox,2TMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1 | 3012.0 | Semi standard non polar | 33892256 | Amlexanox,2TMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1 | 2992.9 | Standard non polar | 33892256 | Amlexanox,2TMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1 | 3628.1 | Standard polar | 33892256 | Amlexanox,2TMS,isomer #2 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1 | 2916.1 | Semi standard non polar | 33892256 | Amlexanox,2TMS,isomer #2 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1 | 3016.7 | Standard non polar | 33892256 | Amlexanox,2TMS,isomer #2 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1 | 3566.6 | Standard polar | 33892256 | Amlexanox,3TMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1 | 2916.0 | Semi standard non polar | 33892256 | Amlexanox,3TMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1 | 3023.0 | Standard non polar | 33892256 | Amlexanox,3TMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1 | 3348.7 | Standard polar | 33892256 | Amlexanox,1TBDMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1 | 3296.3 | Semi standard non polar | 33892256 | Amlexanox,1TBDMS,isomer #2 | CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C(C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1 | 3290.3 | Semi standard non polar | 33892256 | Amlexanox,2TBDMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1 | 3375.1 | Semi standard non polar | 33892256 | Amlexanox,2TBDMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1 | 3323.5 | Standard non polar | 33892256 | Amlexanox,2TBDMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1 | 3738.0 | Standard polar | 33892256 | Amlexanox,2TBDMS,isomer #2 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1 | 3316.4 | Semi standard non polar | 33892256 | Amlexanox,2TBDMS,isomer #2 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1 | 3392.4 | Standard non polar | 33892256 | Amlexanox,2TBDMS,isomer #2 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1 | 3648.5 | Standard polar | 33892256 | Amlexanox,3TBDMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1 | 3479.4 | Semi standard non polar | 33892256 | Amlexanox,3TBDMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1 | 3541.8 | Standard non polar | 33892256 | Amlexanox,3TBDMS,isomer #1 | CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1 | 3583.5 | Standard polar | 33892256 |
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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 - Amlexanox GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-0390000000-7ee61efa9635374d2e64 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Amlexanox GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9456000000-b9624d4096b63a87688a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Amlexanox GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Amlexanox 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 - Amlexanox , positive-QTOF | splash10-0002-0091000000-00993cade43b41e35544 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Amlexanox 35V, Negative-QTOF | splash10-0udi-0090000000-b3b8517df7b9224b9b0f | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Amlexanox 35V, Positive-QTOF | splash10-000t-0090000000-8e4fc4d5f71fd828eec7 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 10V, Positive-QTOF | splash10-0002-0090000000-6251cf97e8c45ca915cd | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 20V, Positive-QTOF | splash10-0zgi-0090000000-4e3a6005c4c7903e8304 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 40V, Positive-QTOF | splash10-000i-2290000000-4ce7d5b38aec871db123 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 10V, Negative-QTOF | splash10-0udj-0090000000-363c3c4f6b29bd793e36 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 20V, Negative-QTOF | splash10-0udi-0090000000-4242451c12a02c097cfc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 40V, Negative-QTOF | splash10-0ktr-2290000000-fe4c8daf1591c12dffa9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 10V, Positive-QTOF | splash10-0002-0090000000-298901b9b72f633ddf1a | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 20V, Positive-QTOF | splash10-001j-0090000000-7ae2b8d3206733616bb9 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 40V, Positive-QTOF | splash10-0udi-0290000000-23dd9de629c968ef59aa | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 10V, Negative-QTOF | splash10-0udi-0090000000-977fc6f1952ba1618211 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 20V, Negative-QTOF | splash10-0udi-0090000000-d126c3ae8460a1113700 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Amlexanox 40V, Negative-QTOF | splash10-01p9-0590000000-299584979cf6ca2fac81 | 2021-10-11 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01025 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01025 | | details |
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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 | DB01025 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 2076 |
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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 | Amlexanox |
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METLIN ID | Not Available |
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PubChem Compound | 2161 |
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PDB ID | ANW |
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ChEBI ID | 31205 |
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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 | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Bell J: Amlexanox for the treatment of recurrent aphthous ulcers. Clin Drug Investig. 2005;25(9):555-66. [PubMed:17532700 ]
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