Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2013-07-09 16:07:21 UTC |
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Update Date | 2021-09-14 15:15:55 UTC |
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HMDB ID | HMDB0060921 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Hydroxyibuprofen |
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Description | 3-Hydroxyibuprofen belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Ibuprofen is known to have an antiplatelet effect, though it is relatively mild and somewhat short-lived when compared with aspirin or other better-known antiplatelet drugs. 3-Hydroxyibuprofen is a metabolite of ibuprofen. 3-Hydroxyibuprofen is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 3-hydroxyibuprofen participates in a number of enzymatic reactions. In particular, 3-hydroxyibuprofen can be biosynthesized from ibuprofen through its interaction with the enzymes cytochrome P450 2C9, cytochrome P450 2C19, and cytochrome P450 2C8. In addition, 3-hydroxyibuprofen can be converted into carboxy-ibuprofen; which is mediated by the enzyme cytochrome P450 2C9. In humans, 3-hydroxyibuprofen is involved in ibuprofen metabolism pathway. Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) used for relief of symptoms of arthritis, fever, as an analgesic (pain reliever), especially where there is an inflammatory component, and dysmenorrhea. |
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Structure | CC(CO)CC1=CC=C(C=C1)C(C)C(O)=O InChI=1S/C13H18O3/c1-9(8-14)7-11-3-5-12(6-4-11)10(2)13(15)16/h3-6,9-10,14H,7-8H2,1-2H3,(H,15,16) |
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Synonyms | Not Available |
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Chemical Formula | C13H18O3 |
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Average Molecular Weight | 222.2802 |
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Monoisotopic Molecular Weight | 222.125594442 |
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IUPAC Name | 2-[4-(3-hydroxy-2-methylpropyl)phenyl]propanoic acid |
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Traditional Name | 2-[4-(3-hydroxy-2-methylpropyl)phenyl]propanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(CO)CC1=CC=C(C=C1)C(C)C(O)=O |
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InChI Identifier | InChI=1S/C13H18O3/c1-9(8-14)7-11-3-5-12(6-4-11)10(2)13(15)16/h3-6,9-10,14H,7-8H2,1-2H3,(H,15,16) |
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InChI Key | HFAIHLSDLUYLQA-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Phenylpropanoic acids |
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Sub Class | Not Available |
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Direct Parent | Phenylpropanoic acids |
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Alternative Parents | |
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Substituents | - 2-phenylpropanoic-acid
- P-cymene
- Aromatic monoterpenoid
- Monocyclic monoterpenoid
- Monoterpenoid
- Phenylpropane
- Monocyclic benzene moiety
- Benzenoid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organooxygen compound
- Alcohol
- Carbonyl group
- Primary alcohol
- Hydrocarbon derivative
- Organic oxide
- 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 | |
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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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3-Hydroxyibuprofen,1TMS,isomer #1 | CC(CO[Si](C)(C)C)CC1=CC=C(C(C)C(=O)O)C=C1 | 1896.4 | Semi standard non polar | 33892256 | 3-Hydroxyibuprofen,1TMS,isomer #2 | CC(CO)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C)C=C1 | 1869.8 | Semi standard non polar | 33892256 | 3-Hydroxyibuprofen,2TMS,isomer #1 | CC(CO[Si](C)(C)C)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C)C=C1 | 1879.6 | Semi standard non polar | 33892256 | 3-Hydroxyibuprofen,1TBDMS,isomer #1 | CC(CO[Si](C)(C)C(C)(C)C)CC1=CC=C(C(C)C(=O)O)C=C1 | 2158.4 | Semi standard non polar | 33892256 | 3-Hydroxyibuprofen,1TBDMS,isomer #2 | CC(CO)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1 | 2118.4 | Semi standard non polar | 33892256 | 3-Hydroxyibuprofen,2TBDMS,isomer #1 | CC(CO[Si](C)(C)C(C)(C)C)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1 | 2347.3 | 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 - 3-Hydroxyibuprofen GC-MS (Non-derivatized) - 70eV, Positive | splash10-03xs-1910000000-faafb3e6e981c8bed49e | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxyibuprofen GC-MS (2 TMS) - 70eV, Positive | splash10-0fg9-6492000000-93d58754b353e3f668f0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxyibuprofen GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxyibuprofen 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 - 3-Hydroxyibuprofen 10V, Positive-QTOF | splash10-0ab9-0590000000-6ba17ecc017cd89a329a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 20V, Positive-QTOF | splash10-0a4i-1930000000-621b8c2cc30713fa687d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 40V, Positive-QTOF | splash10-0aos-3900000000-32ad63b7b1b422462aa7 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 10V, Negative-QTOF | splash10-00di-0390000000-b124c0f38802019877aa | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 20V, Negative-QTOF | splash10-05i0-0950000000-8c00977ae4c9d74b14ed | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 40V, Negative-QTOF | splash10-05mk-6900000000-b843e046ba2a268adacb | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 10V, Positive-QTOF | splash10-0a6r-0960000000-e33bf7c9cfc7ebbd3d54 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 20V, Positive-QTOF | splash10-0a5i-0920000000-5afbcf27502ad97f56b1 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 40V, Positive-QTOF | splash10-0a4i-1900000000-7ce6d6b61dbc558517ea | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 10V, Negative-QTOF | splash10-00di-0090000000-e5cd496528956fe125ac | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 20V, Negative-QTOF | splash10-0002-0920000000-dab699c3f3b1957f2c1b | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 40V, Negative-QTOF | splash10-014i-1900000000-0870f9e15374a842ad52 | 2021-10-12 | Wishart Lab | View Spectrum |
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