| 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 Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 7.02 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 18.3732 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 2.82 minutes | 32390414 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 2635.9 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 653.0 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 257.4 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 417.4 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 539.5 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 862.4 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 911.2 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 116.1 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 1376.6 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 656.8 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 2016.1 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 525.2 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 613.0 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 736.7 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 368.5 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 88.1 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized |
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| Spectra |
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| GC-MS Spectra| Spectrum 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 Spectra| Spectrum 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 Spectra| Spectrum 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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