9-Hydroxyphenanthrene (CHEM003945)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-10-14 21:20:37 UTC
Update Date2026-04-03 01:22:59 UTC
Accession NumberCHEM003945
Identification
Common Name9-Hydroxyphenanthrene
ClassSmall Molecule
DescriptionThis 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Metabolite
  • Natural Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
9-PhenanthrenolChEBI
9-PhenanthrolKegg
9-HydroxyphenanthreneChEBI
Chemical FormulaC14H10O
Average Molecular Mass194.229 g/mol
Monoisotopic Mass194.073 g/mol
CAS Registry Number484-17-3
IUPAC Namephenanthren-9-ol
Traditional Name9-phenanthrol
SMILESOC1=CC2=CC=CC=C2C2=CC=CC=C12
InChI IdentifierInChI=1S/C14H10O/c15-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,15H
InChI KeyDZKIUEHLEXLYKM-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassPhenanthrols
Direct ParentPhenanthrols
Alternative Parents
Substituents
  • Phenanthrol
  • 1-naphthol
  • 2-naphthol
  • Naphthalene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point139-143 C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0087 g/LALOGPS
logP4.12ALOGPS
logP3.65ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.37ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.94 m³·mol⁻¹ChemAxon
Polarizability21.37 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1890000000-1dd35517f58aeb7efc63Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1890000000-1dd35517f58aeb7efc63Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-0900000000-d62d26feaf14fd0bea8cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-7390000000-a2de0eb7a957b02efeb5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-eec5be04bf8c765954d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-b5972ed30b35d36f4ce7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0900000000-e8f817e93e9ab6607731Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-c1fbef549c7eed77a2deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-6f4e10f72a298895b114Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-fe0d908c12a5b5b3e4d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-27ce7a0a54d46fbd9a75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-27ce7a0a54d46fbd9a75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0900000000-8800aa8c6275ef53fdd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-8d1a6691fd9f5b8c101fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-8d1a6691fd9f5b8c101fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-4f22f1e669a6b1bfa56bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of Toxicity9-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)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0059801
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhenanthrenoid
Chemspider IDNot Available
ChEBI ID28820
PubChem Compound ID10229
Kegg Compound IDC11430
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
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.