9-Hydroxyphenanthrene (T3D4991)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-10-14 21:20:37 UTC
Update Date2014-12-24 20:27:01 UTC
Accession NumberT3D4991
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.
Compound Type
  • Animal Toxin
  • Metabolite
  • Natural Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
9-phenanthrenol
9-phenanthrol
phenanthren-9-ol
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 KeyInChIKey=DZKIUEHLEXLYKM-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
LogPNot 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 RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1890000000-1dd35517f58aeb7efc632017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1890000000-1dd35517f58aeb7efc632018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-0900000000-d62d26feaf14fd0bea8c2017-09-20View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-7390000000-a2de0eb7a957b02efeb52017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-eec5be04bf8c765954d32016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-b5972ed30b35d36f4ce72016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0900000000-e8f817e93e9ab66077312016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-c1fbef549c7eed77a2de2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-6f4e10f72a298895b1142016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-fe0d908c12a5b5b3e4d12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-27ce7a0a54d46fbd9a752021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-27ce7a0a54d46fbd9a752021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0900000000-8800aa8c6275ef53fdd32021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-8d1a6691fd9f5b8c101f2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-8d1a6691fd9f5b8c101f2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-4f22f1e669a6b1bfa56b2021-09-24View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB59801
PubChem Compound ID10229
ChEMBL IDNot Available
ChemSpider ID9812
KEGG IDC11430
UniProt IDNot Available
OMIM ID
ChEBI ID28820
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4991.pdf
General References
  1. Guinamard R, Hof T, Del Negro CA: The TRPM4 channel inhibitor 9-phenanthrol. Br J Pharmacol. 2014 Apr;171(7):1600-13. doi: 10.1111/bph.12582. [24433510 ]
  2. Wang J, Takahashi K, Piao H, Qu P, Naruse K: 9-Phenanthrol, a TRPM4 inhibitor, protects isolated rat hearts from ischemia-reperfusion injury. PLoS One. 2013 Jul 25;8(7):e70587. doi: 10.1371/journal.pone.0070587. Print 2013. [23936231 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available