Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2013-03-04 20:33:19 UTC |
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Update Date | 2023-02-21 17:29:25 UTC |
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HMDB ID | HMDB0059801 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 9-Hydroxyphenanthrene |
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Description | 9-Hydroxyphenanthrene, also known as 9-phenanthrol, belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. TRPM4 has been linked to diverse physiological functions such as protection against Ca2+ overload, regulating the levels of intracellular ATP and reactive oxygen species, and cell death. 9-Hydroxyphenanthrene is an extremely weak basic (essentially neutral) compound (based on its pKa). 9-Hydroxyphenanthrene is a potentially toxic compound. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. 9-Hydroxyphenanthrene is a recently identified inhibitor of the transient receptor potential melastatin (TRPM) 4 channel, a Ca(2+) -activated non-selective cation channel whose mechanism of action remains to be determined. 9-Hydroxyphenanthrene modulates a variety of physiological processes through TRPM4 current inhibition. TRPM4 in neurons contributes toward inflammation-induced neurodegeneration by mediating cell death, which corresponds to the cardioprotective effect of 9-phenanthrol. Damage induced by ischemia/reperfusion (I/R) was caused by TPRM4-dependent cell death and that 9-phenanthorol induces cardioprotection by blocking this pathway. The most specific inhibitor of TRPM4 channels currently available is 9-phenanthrol, which abolishes arrhythmias induced by hypoxia and reoxygenation in the mouse ventricle. |
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Structure | OC1=CC2=CC=CC=C2C2=CC=CC=C12 InChI=1S/C14H10O/c15-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,15H |
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Synonyms | Value | Source |
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9-Phenanthrenol | ChEBI | 9-Phenanthrol | Kegg | 9-Hydroxyphenanthrene | ChEBI |
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Chemical Formula | C14H10O |
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Average Molecular Weight | 194.2286 |
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Monoisotopic Molecular Weight | 194.073164942 |
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IUPAC Name | phenanthren-9-ol |
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Traditional Name | 9-phenanthrol |
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CAS Registry Number | Not Available |
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SMILES | OC1=CC2=CC=CC=C2C2=CC=CC=C12 |
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InChI Identifier | InChI=1S/C14H10O/c15-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,15H |
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InChI Key | DZKIUEHLEXLYKM-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenanthrenes and derivatives |
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Sub Class | Phenanthrols |
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Direct Parent | Phenanthrols |
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Alternative Parents | |
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Substituents | - Phenanthrol
- 1-naphthol
- 2-naphthol
- Naphthalene
- 1-hydroxy-2-unsubstituted benzenoid
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic 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 | 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 IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 9-Hydroxyphenanthrene GC-EI-TOF (Non-derivatized) | splash10-014i-1890000000-1dd35517f58aeb7efc63 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 9-Hydroxyphenanthrene GC-EI-TOF (Non-derivatized) | splash10-014i-1890000000-1dd35517f58aeb7efc63 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 9-Hydroxyphenanthrene GC-MS (Non-derivatized) - 70eV, Positive | splash10-00kf-0900000000-d62d26feaf14fd0bea8c | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 9-Hydroxyphenanthrene GC-MS (1 TMS) - 70eV, Positive | splash10-0fk9-7390000000-a2de0eb7a957b02efeb5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 9-Hydroxyphenanthrene 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 - 9-Hydroxyphenanthrene 10V, Positive-QTOF | splash10-0002-0900000000-eec5be04bf8c765954d3 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 20V, Positive-QTOF | splash10-0002-0900000000-b5972ed30b35d36f4ce7 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 40V, Positive-QTOF | splash10-004i-0900000000-e8f817e93e9ab6607731 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 10V, Negative-QTOF | splash10-0006-0900000000-c1fbef549c7eed77a2de | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 20V, Negative-QTOF | splash10-0006-0900000000-6f4e10f72a298895b114 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 40V, Negative-QTOF | splash10-0006-0900000000-fe0d908c12a5b5b3e4d1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 10V, Positive-QTOF | splash10-0002-0900000000-27ce7a0a54d46fbd9a75 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 20V, Positive-QTOF | splash10-0002-0900000000-27ce7a0a54d46fbd9a75 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 40V, Positive-QTOF | splash10-014j-0900000000-8800aa8c6275ef53fdd3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 10V, Negative-QTOF | splash10-0006-0900000000-8d1a6691fd9f5b8c101f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 20V, Negative-QTOF | splash10-0006-0900000000-8d1a6691fd9f5b8c101f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 9-Hydroxyphenanthrene 40V, Negative-QTOF | splash10-0006-0900000000-4f22f1e669a6b1bfa56b | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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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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Urine | Detected and Quantified | 0.00053 umol/mmol creatinine | Adult (>18 years old) | Male | Roofers (post shift) | | details | Urine | Detected and Quantified | 0.000095-0.00102 umol/mmol creatinine | Adult (>18 years old) | Male | Workers in coking plants | | 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 | C11430 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Phenanthrenoid |
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METLIN ID | Not Available |
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PubChem Compound | 10229 |
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PDB ID | Not Available |
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ChEBI ID | 28820 |
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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 | - Grand T, Demion M, Norez C, Mettey Y, Launay P, Becq F, Bois P, Guinamard R: 9-phenanthrol inhibits human TRPM4 but not TRPM5 cationic channels. Br J Pharmacol. 2008 Apr;153(8):1697-705. doi: 10.1038/bjp.2008.38. Epub 2008 Feb 25. [PubMed:18297105 ]
- Burris SK, Wang Q, Bulley S, Neeb ZP, Jaggar JH: 9-Phenanthrol inhibits recombinant and arterial myocyte TMEM16A channels. Br J Pharmacol. 2015 May;172(10):2459-68. doi: 10.1111/bph.13077. Epub 2015 Mar 24. [PubMed:25573456 ]
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