Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-06-12 17:33:17 UTC |
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Update Date | 2019-07-23 07:14:34 UTC |
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HMDB ID | HMDB0060545 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | O-Desmethylindomethacin |
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Description | O-Desmethylindomethacin is a metaboite of Indomethacin. Indomethacin is metabolized in humans by O-demethylation, and by acyl glucuronidation to the 1-O-glucuronide. Indomethacin and O-desmethylindomethacin may be glucuronidated in the kidney. Probenecid is a known substrate for renal glucuronidation. If indomethacin is glucuronidated in the human kidney like probenecid, then this glucuronidation might be reduced or inhibited under probenecid co-medication. (PMID: 8156046 ) |
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Structure | CC1=C(CC(O)=O)C2=C(C=CC(O)=C2)N1C(=O)C1=CC=C(Cl)C=C1 InChI=1S/C18H14ClNO4/c1-10-14(9-17(22)23)15-8-13(21)6-7-16(15)20(10)18(24)11-2-4-12(19)5-3-11/h2-8,21H,9H2,1H3,(H,22,23) |
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Synonyms | Value | Source |
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Desmethyl-indomethacin | HMDB | 5-Hydroxyindomethacin sulfate(1:1) | HMDB | 5-Hydroxyindomethacin | HMDB |
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Chemical Formula | C18H14ClNO4 |
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Average Molecular Weight | 343.761 |
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Monoisotopic Molecular Weight | 343.061135648 |
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IUPAC Name | 2-[1-(4-chlorobenzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]acetic acid |
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Traditional Name | [1-(4-chlorobenzoyl)-5-hydroxy-2-methylindol-3-yl]acetic acid |
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CAS Registry Number | Not Available |
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SMILES | CC1=C(CC(O)=O)C2=C(C=CC(O)=C2)N1C(=O)C1=CC=C(Cl)C=C1 |
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InChI Identifier | InChI=1S/C18H14ClNO4/c1-10-14(9-17(22)23)15-8-13(21)6-7-16(15)20(10)18(24)11-2-4-12(19)5-3-11/h2-8,21H,9H2,1H3,(H,22,23) |
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InChI Key | KMLNWQPYFBIALN-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Benzoylindoles |
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Direct Parent | Benzoylindoles |
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Alternative Parents | |
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Substituents | - Benzoylindole
- Indole-3-acetic acid derivative
- Indolyl carboxylic acid derivative
- Indolecarboxylic acid derivative
- 4-halobenzoic acid or derivatives
- Halobenzoic acid or derivatives
- 3-alkylindole
- Hydroxyindole
- Indole
- Benzoic acid or derivatives
- Benzoyl
- 1-hydroxy-2-unsubstituted benzenoid
- Chlorobenzene
- Halobenzene
- Monocyclic benzene moiety
- Benzenoid
- Aryl chloride
- Substituted pyrrole
- Aryl halide
- Pyrrole
- Heteroaromatic compound
- Azacycle
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organooxygen compound
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Organopnictogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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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 | Not Available |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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O-Desmethylindomethacin,1TMS,isomer #1 | CC1=C(CC(=O)O[Si](C)(C)C)C2=CC(O)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 | 2957.7 | Semi standard non polar | 33892256 | O-Desmethylindomethacin,1TMS,isomer #2 | CC1=C(CC(=O)O)C2=CC(O[Si](C)(C)C)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 | 3023.4 | Semi standard non polar | 33892256 | O-Desmethylindomethacin,2TMS,isomer #1 | CC1=C(CC(=O)O[Si](C)(C)C)C2=CC(O[Si](C)(C)C)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 | 2976.1 | Semi standard non polar | 33892256 | O-Desmethylindomethacin,1TBDMS,isomer #1 | CC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C2=CC(O)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 | 3209.9 | Semi standard non polar | 33892256 | O-Desmethylindomethacin,1TBDMS,isomer #2 | CC1=C(CC(=O)O)C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 | 3270.1 | Semi standard non polar | 33892256 | O-Desmethylindomethacin,2TBDMS,isomer #1 | CC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 | 3410.1 | Semi standard non 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 - O-Desmethylindomethacin GC-MS (Non-derivatized) - 70eV, Positive | splash10-01p9-0931000000-08ae12731d1009bab9ae | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - O-Desmethylindomethacin GC-MS (2 TMS) - 70eV, Positive | splash10-000i-4904200000-d43c7bc4448e17e0ca47 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - O-Desmethylindomethacin 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 - O-Desmethylindomethacin 10V, Positive-QTOF | splash10-004i-0019000000-abf0492a0a23ca9511fc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 20V, Positive-QTOF | splash10-000j-0975000000-7947cf8b43da961e7f14 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 40V, Positive-QTOF | splash10-000i-3900000000-fba681a2d0d88f7f3dc3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 10V, Negative-QTOF | splash10-0007-0049000000-57ec60062d75239701c5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 20V, Negative-QTOF | splash10-006y-0259000000-8a8c589ccae2bd36ca5a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 40V, Negative-QTOF | splash10-03dr-0930000000-2a8b45256d5adfe18cea | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 10V, Positive-QTOF | splash10-0006-0109000000-c78beb1d062424159de8 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 20V, Positive-QTOF | splash10-000i-0966000000-95e708ac9d20e69a0e9f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 40V, Positive-QTOF | splash10-000i-0900000000-e31bba49f73999be4ea9 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 10V, Negative-QTOF | splash10-0005-0095000000-7c37ad6d5b3366099ab6 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 20V, Negative-QTOF | splash10-0002-1191000000-8d8abc587d2acc238db2 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - O-Desmethylindomethacin 40V, Negative-QTOF | splash10-001i-7950000000-13ee36355249a28d2125 | 2021-10-12 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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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 | Normal | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | 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 | Not Available |
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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 | Not Available |
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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 | Not Available |
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PubChem Compound | 159665 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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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 | Not Available |
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