T3DB: 9-Hydroxyphenanthrene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation XML

Record Information

Version

2.0

Creation Date

2014-10-14 21:20:37 UTC

Update Date

2014-12-24 20:27:01 UTC

Accession Number

T3D4991

Identification

Common Name

9-Hydroxyphenanthrene

Class

Small Molecule

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.

Compound Type

Animal Toxin
Metabolite
Natural Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Chemical Formula

C₁₄H₁₀O

Average Molecular Mass

194.229 g/mol

Monoisotopic Mass

194.073 g/mol

CAS Registry Number

484-17-3

IUPAC Name

phenanthren-9-ol

Traditional Name

9-phenanthrol

SMILES

OC1=CC2=CC=CC=C2C2=CC=CC=C12

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

InChI Key

InChIKey=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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

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 Framework

Aromatic homopolycyclic compounds

External Descriptors

phenanthrol (CHEBI:28820 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	139-143 C
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0087 g/L	ALOGPS
logP	4.12	ALOGPS
logP	3.65	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.37	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	60.94 m³·mol⁻¹	ChemAxon
Polarizability	21.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1890000000-1dd35517f58aeb7efc63	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1890000000-1dd35517f58aeb7efc63	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-0900000000-d62d26feaf14fd0bea8c	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-7390000000-a2de0eb7a957b02efeb5	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-eec5be04bf8c765954d3	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-b5972ed30b35d36f4ce7	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0900000000-e8f817e93e9ab6607731	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-c1fbef549c7eed77a2de	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-6f4e10f72a298895b114	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0900000000-fe0d908c12a5b5b3e4d1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-27ce7a0a54d46fbd9a75	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-27ce7a0a54d46fbd9a75	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-0900000000-8800aa8c6275ef53fdd3	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-8d1a6691fd9f5b8c101f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-8d1a6691fd9f5b8c101f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0900000000-4f22f1e669a6b1bfa56b	2021-09-24	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

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)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB59801

PubChem Compound ID

10229

ChEMBL ID

Not Available

ChemSpider ID

9812

KEGG ID

C11430

UniProt ID

Not Available

OMIM ID

ChEBI ID

28820

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D4991.pdf

General References

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 ]
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 Genes

Not Available

Down-Regulated Genes

Not Available

9-Hydroxyphenanthrene (T3D4991)

Structure for T3D4991: 9-Hydroxyphenanthrene