Record Information |
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Version | 1.0 |
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Creation Date | 2014-10-14 21:20:37 UTC |
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Update Date | 2016-11-09 01:09:15 UTC |
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Accession Number | CHEM003945 |
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Identification |
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Common Name | 9-Hydroxyphenanthrene |
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Class | Small Molecule |
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Description | This compound belongs to the family of Phenanthrenes and Derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. |
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Contaminant Sources | - HMDB Contaminants - Urine
- T3DB toxins
- ToxCast & Tox21 Chemicals
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Contaminant Type | - Animal Toxin
- Metabolite
- Natural Compound
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Chemical Structure | |
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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 Mass | 194.229 g/mol |
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Monoisotopic Mass | 194.073 g/mol |
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CAS Registry Number | 484-17-3 |
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IUPAC Name | phenanthren-9-ol |
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Traditional Name | 9-phenanthrol |
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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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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | 139-143 C | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | 9-phenanthrol 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-phenanthrol modulates a variety of physiological processes through TRPM4 current inhibition. 9-Phenanthrol modulates smooth muscle contraction in bladder and cerebral arteries, affects spontaneous activity in neurons and in the heart, and reduces lipopolysaccharide-induced cell death. 9-phenanthrol exerts cardioprotective effects against ischaemia-reperfusion injuries and reduces ischaemic stroke injuries. (1) The most specific inhibitor of TRPM4 channels currently available is 9-phenanthrol, which abolishes arrhythmias induced by hypoxia and reoxygenation in the mouse ventricle. 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. 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. (2) |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0059801 |
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FooDB ID | Not Available |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Phenanthrenoid |
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Chemspider ID | Not Available |
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ChEBI ID | 28820 |
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PubChem Compound ID | 10229 |
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Kegg Compound ID | C11430 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18297105 | 2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22014185 | 3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22815468 | 4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23831210 | 5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23936231 | 6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24037125 | 7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24433510 | 8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25323322 | 9. https://www.ncbi.nlm.nih.gov/pubmed/?term=25573456 | 10. 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. | 11. 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. |
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