NP-MRD: Showing NP-Card for 9-phenanthrol (NP0321502)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 23:44:34 UTC

Updated at

2022-09-11 23:44:34 UTC

NP-MRD ID

NP0321502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-phenanthrol

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. 9-phenanthrol is found in Streptomyces flavovirens. 9-phenanthrol was first documented in 2008 (PMID: 18297105). The most specific inhibitor of TRPM4 channels currently available is 9-phenanthrol, which abolishes arrhythmias induced by hypoxia and reoxygenation in the mouse ventricle (PMID: 22014185) (PMID: 23831210) (PMID: 23936231).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 03041314042D          

 15 17  0  0  0  0            999 V2000
    4.7289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 12  7  2  0  0  0  0
 12 11  1  0  0  0  0
 13  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14  9  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321502

> <DATABASE_NAME>
NP-MRD

> <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>
DZKIUEHLEXLYKM-UHFFFAOYSA-N

> <FORMULA>
C14H10O

> <MOLECULAR_WEIGHT>
194.2286

> <EXACT_MASS>
194.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
21.366330775958534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
phenanthren-9-ol

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
3.6486340076666663

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.374701622391084

> <JCHEM_PKA_STRONGEST_BASIC>
-5.614643628583505

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
60.93930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.68e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-phenanthrol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-MAR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAR-13         0                                  
HETATM    1  C   UNK     0       8.827   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.057   4.414   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.897   4.414   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.127   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.057   1.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.517   4.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.437   4.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.897   1.746   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747   0.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.517   1.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.437   1.746   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.207   0.413   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.437  -0.921   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    1   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   13                                                       
CONECT    9   10   14                                                       
CONECT   10    5    9   11                                                  
CONECT   11    6   10   12                                                  
CONECT   12    7   11   13                                                  
CONECT   13    8   12   14                                                  
CONECT   14    9   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Value	Source
9-Phenanthrenol	ChEBI
9-Phenanthrol	Kegg
9-Hydroxyphenanthrene	ChEBI

Chemical Formula

C₁₄H₁₀O

Average Mass

194.2286 Da

Monoisotopic Mass

194.07316 Da

IUPAC Name

phenanthren-9-ol

Traditional Name

9-phenanthrol

CAS Registry Number

Not Available

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

DZKIUEHLEXLYKM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces flavovirens	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0059801

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11430

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenanthrenoid

METLIN ID

Not Available

PubChem Compound

10229

PDB ID

Not Available

ChEBI ID

28820

Good Scents ID

Not Available

References

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 ]
Simard C, Salle L, Rouet R, Guinamard R: Transient receptor potential melastatin 4 inhibitor 9-phenanthrol abolishes arrhythmias induced by hypoxia and re-oxygenation in mouse ventricle. Br J Pharmacol. 2012 Apr;165(7):2354-64. doi: 10.1111/j.1476-5381.2011.01715.x. [PubMed:22014185 ]
Burt R, Graves BM, Gao M, Li C, Williams DL, Fregoso SP, Hoover DB, Li Y, Wright GL, Wondergem R: 9-Phenanthrol and flufenamic acid inhibit calcium oscillations in HL-1 mouse cardiomyocytes. Cell Calcium. 2013 Sep;54(3):193-201. doi: 10.1016/j.ceca.2013.06.003. Epub 2013 Jul 5. [PubMed:23831210 ]
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. [PubMed:23936231 ]
LOTUS database [Link]

Showing NP-Card for 9-phenanthrol (NP0321502)

MOL for NP0321502 (9-phenanthrol)

3D MOL for NP0321502 (9-phenanthrol)

3D SDF for NP0321502 (9-phenanthrol)

3D-SDF for NP0321502 (9-phenanthrol)

PDB for NP0321502 (9-phenanthrol)

3D PDB for NP0321502 (9-phenanthrol)

SMILES for NP0321502 (9-phenanthrol)

INCHI for NP0321502 (9-phenanthrol)

Structure for NP0321502 (9-phenanthrol)

3D Structure for NP0321502 (9-phenanthrol)