Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-04 18:58:24 UTC |
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Update Date | 2019-07-23 07:15:03 UTC |
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HMDB ID | HMDB0060770 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4'-Hydroxy-5-carboxy-lumiracoxib |
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Description | 4'-Hydroxy-5-carboxy-lumiracoxib belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Lumiracoxib is a COX-2 selective inhibitor non-steroidal anti-inflammatory drug, manufactured by Novartis and still sold in few countries, including Mexico, Ecuador and the Dominican Republic, under the trade name Prexige (sometimes misquoted as 'Prestige' by the media). 4'-Hydroxy-5-carboxy-lumiracoxib is a metabolite of lumiracoxib. 4'-Hydroxy-5-carboxy-lumiracoxib is an extremely weak basic (essentially neutral) compound (based on its pKa). Lumiracoxib has several distinctive features. |
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Structure | CC1=CC(CC(O)=O)=C(NC2=C(F)C(C(O)=O)=C(O)C=C2Cl)C=C1 InChI=1S/C16H13ClFNO5/c1-7-2-3-10(8(4-7)5-12(21)22)19-15-9(17)6-11(20)13(14(15)18)16(23)24/h2-4,6,19-20H,5H2,1H3,(H,21,22)(H,23,24) |
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Synonyms | Not Available |
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Chemical Formula | C16H13ClFNO5 |
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Average Molecular Weight | 353.73 |
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Monoisotopic Molecular Weight | 353.046628443 |
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IUPAC Name | 3-{[2-(carboxymethyl)-4-methylphenyl]amino}-4-chloro-2-fluoro-6-hydroxybenzoic acid |
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Traditional Name | 3-{[2-(carboxymethyl)-4-methylphenyl]amino}-4-chloro-2-fluoro-6-hydroxybenzoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC1=CC(CC(O)=O)=C(NC2=C(F)C(C(O)=O)=C(O)C=C2Cl)C=C1 |
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InChI Identifier | InChI=1S/C16H13ClFNO5/c1-7-2-3-10(8(4-7)5-12(21)22)19-15-9(17)6-11(20)13(14(15)18)16(23)24/h2-4,6,19-20H,5H2,1H3,(H,21,22)(H,23,24) |
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InChI Key | QQKNIFQTDAHPAP-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | Aminobenzoic acids |
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Alternative Parents | |
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Substituents | - Hydroxybenzoic acid
- Salicylic acid or derivatives
- Aminobenzoic acid
- Salicylic acid
- 2-halobenzoic acid or derivatives
- 4-halobenzoic acid or derivatives
- Halobenzoic acid or derivatives
- 2-halobenzoic acid
- 4-halobenzoic acid
- Halobenzoic acid
- Benzoic acid
- 3-halophenol
- 3-chlorophenol
- 3-fluorophenol
- Benzoyl
- P-aminophenol
- Aminophenol
- 1-carboxy-2-haloaromatic compound
- Aminotoluene
- Aniline or substituted anilines
- Fluorobenzene
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Toluene
- Chlorobenzene
- Halobenzene
- Aryl halide
- Dicarboxylic acid or derivatives
- Aryl chloride
- Aryl fluoride
- Vinylogous acid
- Vinylogous halide
- Amino acid or derivatives
- Amino acid
- Secondary amine
- Carboxylic acid derivative
- Carboxylic acid
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organofluoride
- Organochloride
- Organohalogen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | |
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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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4'-Hydroxy-5-carboxy-lumiracoxib,1TMS,isomer #1 | CC1=CC=C(NC2=C(Cl)C=C(O)C(C(=O)O)=C2F)C(CC(=O)O[Si](C)(C)C)=C1 | 2764.1 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,1TMS,isomer #2 | CC1=CC=C(NC2=C(Cl)C=C(O)C(C(=O)O[Si](C)(C)C)=C2F)C(CC(=O)O)=C1 | 2768.4 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,1TMS,isomer #3 | CC1=CC=C(NC2=C(Cl)C=C(O[Si](C)(C)C)C(C(=O)O)=C2F)C(CC(=O)O)=C1 | 2821.4 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,1TMS,isomer #4 | CC1=CC=C(N(C2=C(Cl)C=C(O)C(C(=O)O)=C2F)[Si](C)(C)C)C(CC(=O)O)=C1 | 2742.4 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TMS,isomer #1 | CC1=CC=C(NC2=C(Cl)C=C(O[Si](C)(C)C)C(C(=O)O)=C2F)C(CC(=O)O[Si](C)(C)C)=C1 | 2804.9 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TMS,isomer #2 | CC1=CC=C(NC2=C(Cl)C=C(O)C(C(=O)O[Si](C)(C)C)=C2F)C(CC(=O)O[Si](C)(C)C)=C1 | 2759.3 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TMS,isomer #3 | CC1=CC=C(N(C2=C(Cl)C=C(O)C(C(=O)O)=C2F)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1 | 2696.5 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TMS,isomer #4 | CC1=CC=C(NC2=C(Cl)C=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2F)C(CC(=O)O)=C1 | 2825.1 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TMS,isomer #5 | CC1=CC=C(N(C2=C(Cl)C=C(O)C(C(=O)O[Si](C)(C)C)=C2F)[Si](C)(C)C)C(CC(=O)O)=C1 | 2721.0 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TMS,isomer #6 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C)C(C(=O)O)=C2F)[Si](C)(C)C)C(CC(=O)O)=C1 | 2764.2 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,3TMS,isomer #1 | CC1=CC=C(NC2=C(Cl)C=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2F)C(CC(=O)O[Si](C)(C)C)=C1 | 2830.8 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,3TMS,isomer #2 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C)C(C(=O)O)=C2F)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1 | 2745.3 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,3TMS,isomer #3 | CC1=CC=C(N(C2=C(Cl)C=C(O)C(C(=O)O[Si](C)(C)C)=C2F)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1 | 2696.2 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,3TMS,isomer #4 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2F)[Si](C)(C)C)C(CC(=O)O)=C1 | 2767.8 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,4TMS,isomer #1 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2F)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1 | 2776.1 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,4TMS,isomer #1 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2F)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1 | 2685.8 | Standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,4TMS,isomer #1 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2F)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1 | 2984.5 | Standard polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,1TBDMS,isomer #1 | CC1=CC=C(NC2=C(Cl)C=C(O)C(C(=O)O)=C2F)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3027.7 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,1TBDMS,isomer #2 | CC1=CC=C(NC2=C(Cl)C=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)C(CC(=O)O)=C1 | 3031.9 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,1TBDMS,isomer #3 | CC1=CC=C(NC2=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2F)C(CC(=O)O)=C1 | 3081.5 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,1TBDMS,isomer #4 | CC1=CC=C(N(C2=C(Cl)C=C(O)C(C(=O)O)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C1 | 2973.4 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TBDMS,isomer #1 | CC1=CC=C(NC2=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2F)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3271.7 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TBDMS,isomer #2 | CC1=CC=C(NC2=C(Cl)C=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3237.8 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TBDMS,isomer #3 | CC1=CC=C(N(C2=C(Cl)C=C(O)C(C(=O)O)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3154.4 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TBDMS,isomer #4 | CC1=CC=C(NC2=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)C(CC(=O)O)=C1 | 3305.9 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TBDMS,isomer #5 | CC1=CC=C(N(C2=C(Cl)C=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C1 | 3178.2 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,2TBDMS,isomer #6 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C1 | 3202.6 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,3TBDMS,isomer #1 | CC1=CC=C(NC2=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3479.9 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,3TBDMS,isomer #2 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3389.9 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,3TBDMS,isomer #3 | CC1=CC=C(N(C2=C(Cl)C=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3374.5 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,3TBDMS,isomer #4 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C1 | 3419.8 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,4TBDMS,isomer #1 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3609.9 | Semi standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,4TBDMS,isomer #1 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3373.4 | Standard non polar | 33892256 | 4'-Hydroxy-5-carboxy-lumiracoxib,4TBDMS,isomer #1 | CC1=CC=C(N(C2=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1 | 3368.4 | Standard polar | 33892256 |
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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 - 4'-Hydroxy-5-carboxy-lumiracoxib GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-0129000000-821e4472ba0c38d67388 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib GC-MS (3 TMS) - 70eV, Positive | splash10-0zgi-3200970000-cfb9dcd19fdaf31b2d9e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 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 - 4'-Hydroxy-5-carboxy-lumiracoxib 10V, Positive-QTOF | splash10-000i-0019000000-13563121f984216030c7 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 20V, Positive-QTOF | splash10-052o-0259000000-c588bbb065e2f6eaad8b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 40V, Positive-QTOF | splash10-06r5-1391000000-f4a62101e345bbf572f3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 10V, Negative-QTOF | splash10-0zfr-0009000000-985365e74c42e5f0b346 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 20V, Negative-QTOF | splash10-0bt9-0059000000-870c7e7cdb9735d38f53 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 40V, Negative-QTOF | splash10-06r6-2192000000-f43cfe545618a794486a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 10V, Positive-QTOF | splash10-0f79-0019000000-f9a9defef219fa42bd4a | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 20V, Positive-QTOF | splash10-052f-0079000000-2fd52087c48bdc3431ad | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 40V, Positive-QTOF | splash10-000l-0192000000-4f926df6b4289bb606f1 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 10V, Negative-QTOF | splash10-114i-0029000000-4c800fbb80c462ca04d8 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 20V, Negative-QTOF | splash10-06r6-0092000000-97d1626a98b6faaa9aff | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4'-Hydroxy-5-carboxy-lumiracoxib 40V, Negative-QTOF | splash10-001i-9000000000-c2fa753da65a4bac80a1 | 2021-10-12 | Wishart Lab | View Spectrum |
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