Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-22 19:50:39 UTC |
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Update Date | 2021-09-14 15:19:36 UTC |
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HMDB ID | HMDB0061142 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Fenoprofen glucuronide |
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Description | Fenoprofen glucuronide belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. Fenoprofen glucuronide is a metabolite of fenoprofen. Fenoprofen glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Fenoprofen is marketed in the USA as Nalfon. Fenoprofen calcium is used for symptomatic relief for rheumatoid arthritis, osteoarthritis, and mild to moderate pain. Fenoprofen is a non-steroidal anti-inflammatory drug. |
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Structure | CC(C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C1=CC=CC(OC2=CC=CC=C2)=C1 InChI=1S/C21H22O9/c1-11(12-6-5-9-14(10-12)28-13-7-3-2-4-8-13)20(27)30-21-17(24)15(22)16(23)18(29-21)19(25)26/h2-11,15-18,21-24H,1H3,(H,25,26)/t11?,15-,16-,17+,18-,21-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C21H22O9 |
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Average Molecular Weight | 418.394 |
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Monoisotopic Molecular Weight | 418.126382302 |
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IUPAC Name | (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(3-phenoxyphenyl)propanoyl]oxy}oxane-2-carboxylic acid |
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Traditional Name | (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(3-phenoxyphenyl)propanoyl]oxy}oxane-2-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C1=CC=CC(OC2=CC=CC=C2)=C1 |
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InChI Identifier | InChI=1S/C21H22O9/c1-11(12-6-5-9-14(10-12)28-13-7-3-2-4-8-13)20(27)30-21-17(24)15(22)16(23)18(29-21)19(25)26/h2-11,15-18,21-24H,1H3,(H,25,26)/t11?,15-,16-,17+,18-,21-/m0/s1 |
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InChI Key | KXAAUVHIGIFUSM-RVLIQFCMSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | O-glucuronides |
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Alternative Parents | |
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Substituents | - 1-o-glucuronide
- O-glucuronide
- Diphenylether
- Diaryl ether
- Phenoxy compound
- Phenol ether
- Beta-hydroxy acid
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Hydroxy acid
- Monosaccharide
- Oxane
- Benzenoid
- Pyran
- Carboxylic acid ester
- Secondary alcohol
- Acetal
- Ether
- Carboxylic acid
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Carboxylic acid derivative
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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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Fenoprofen glucuronide,1TMS,isomer #1 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3187.1 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,1TMS,isomer #2 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3188.4 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,1TMS,isomer #3 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3192.5 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,1TMS,isomer #4 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3188.2 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TMS,isomer #1 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3196.2 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TMS,isomer #2 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3192.3 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TMS,isomer #3 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3195.2 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TMS,isomer #4 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3196.0 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TMS,isomer #5 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3191.7 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TMS,isomer #6 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3191.2 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,3TMS,isomer #1 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3222.7 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,3TMS,isomer #2 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3230.6 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,3TMS,isomer #3 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3222.1 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,3TMS,isomer #4 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3218.7 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,4TMS,isomer #1 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3265.0 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,1TBDMS,isomer #1 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3443.4 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,1TBDMS,isomer #2 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3453.8 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,1TBDMS,isomer #3 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3452.2 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,1TBDMS,isomer #4 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3445.5 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TBDMS,isomer #1 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3692.0 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TBDMS,isomer #2 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3668.4 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TBDMS,isomer #3 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3671.8 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TBDMS,isomer #4 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3679.1 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TBDMS,isomer #5 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3665.2 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,2TBDMS,isomer #6 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3688.2 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,3TBDMS,isomer #1 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3856.4 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,3TBDMS,isomer #2 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3880.4 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,3TBDMS,isomer #3 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3842.1 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,3TBDMS,isomer #4 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 3855.6 | Semi standard non polar | 33892256 | Fenoprofen glucuronide,4TBDMS,isomer #1 | CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1 | 4036.5 | Semi standard non 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 - Fenoprofen glucuronide GC-MS (Non-derivatized) - 70eV, Positive | splash10-052b-9411100000-142771712eb35c6fb6c4 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Fenoprofen glucuronide GC-MS (3 TMS) - 70eV, Positive | splash10-00rb-9652025000-3bc2c854dbd008b5e154 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Fenoprofen glucuronide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Fenoprofen glucuronide 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 - Fenoprofen glucuronide 10V, Positive-QTOF | splash10-004l-0390400000-13b0912c22b13e64851f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 20V, Positive-QTOF | splash10-004i-1590100000-466020693e565d13abd9 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 40V, Positive-QTOF | splash10-002b-3930000000-4d1b438cd4625c03d061 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 10V, Negative-QTOF | splash10-00r6-1293400000-5c91fc2ec1f6dee9782a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 20V, Negative-QTOF | splash10-0006-6893000000-00765df1c5a363205ddb | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 40V, Negative-QTOF | splash10-0006-9420000000-c306a37bf66053cc9aa1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 10V, Positive-QTOF | splash10-0fba-1791600000-839c4054c99a08669418 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 20V, Positive-QTOF | splash10-0002-0920000000-34790b42da973a9af41e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 40V, Positive-QTOF | splash10-004j-5900000000-6c9293e8448c4af7afa3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 10V, Negative-QTOF | splash10-014l-1460900000-f1e6424a6b2d61696aae | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 20V, Negative-QTOF | splash10-014m-3964300000-4be8b5cc8c7f69527ffc | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Fenoprofen glucuronide 40V, Negative-QTOF | splash10-0006-9630000000-932c217ac1f0e1c4fae1 | 2021-09-25 | Wishart Lab | View Spectrum |
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