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Showing metabocard for 9-Hydroxyphenanthrene (HMDB0059801)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-03-04 20:33:19 UTC
Update Date2023-02-21 17:29:25 UTC
HMDB IDHMDB0059801
Secondary Accession Numbers
  • HMDB59801
Metabolite Identification
Common Name9-Hydroxyphenanthrene
Description9-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.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0059801 (9-Hydroxyphenanthrene)

  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
Download

3D MOL for HMDB0059801 (9-Hydroxyphenanthrene)

HMDB0059801
     RDKit          3D
9-Hydroxyphenanthrene
 25 27  0  0  0  0  0  0  0  0999 V2000
   -1.9271    2.7325    0.0209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9926    1.7121    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3404    2.0275    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2680    0.9903    0.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6066    1.2505    0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5129    0.2180    0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957   -1.0815    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7312   -1.3627    0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -0.3338    0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5132   -0.6188   -0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -1.8940   -0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3398   -2.1221   -0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2499   -1.0956   -0.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935    0.1915   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176    0.4208   -0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6472    3.6764    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    3.0407    0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    2.2814    0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858    0.4473    0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631   -1.9277    0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388   -2.3920   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642   -2.7765   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7382   -3.1262   -0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3125   -1.2709   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4816    1.0130   -0.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  2  1  0
  9  4  1  0
 15 10  1  0
  1 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
 11 22  1  0
 12 23  1  0
 13 24  1  0
 14 25  1  0
M  END
Download

3D SDF for HMDB0059801 (9-Hydroxyphenanthrene)

  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>
HMDB0059801

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0059801 (9-Hydroxyphenanthrene)

HMDB0059801
     RDKit          3D
9-Hydroxyphenanthrene
 25 27  0  0  0  0  0  0  0  0999 V2000
   -1.9271    2.7325    0.0209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9926    1.7121    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3404    2.0275    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2680    0.9903    0.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6066    1.2505    0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5129    0.2180    0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957   -1.0815    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7312   -1.3627    0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -0.3338    0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5132   -0.6188   -0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -1.8940   -0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3398   -2.1221   -0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2499   -1.0956   -0.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935    0.1915   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176    0.4208   -0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6472    3.6764    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    3.0407    0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    2.2814    0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858    0.4473    0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631   -1.9277    0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388   -2.3920   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642   -2.7765   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7382   -3.1262   -0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3125   -1.2709   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4816    1.0130   -0.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  2  1  0
  9  4  1  0
 15 10  1  0
  1 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
 11 22  1  0
 12 23  1  0
 13 24  1  0
 14 25  1  0
M  END
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PDB for HMDB0059801 (9-Hydroxyphenanthrene)

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
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3D PDB for HMDB0059801 (9-Hydroxyphenanthrene)

COMPND    HMDB0059801
HETATM    1  O1  UNL     1      -1.927   2.732   0.021  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.993   1.712   0.031  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.340   2.027   0.167  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.268   0.990   0.176  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.607   1.250   0.308  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.513   0.218   0.316  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.096  -1.082   0.191  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.731  -1.363   0.056  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.825  -0.334   0.048  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.513  -0.619  -0.086  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.968  -1.894  -0.212  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.340  -2.122  -0.345  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.250  -1.096  -0.353  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.793   0.192  -0.226  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.418   0.421  -0.093  1.00  0.00           C  
HETATM   16  H1  UNL     1      -1.647   3.676   0.109  1.00  0.00           H  
HETATM   17  H2  UNL     1       0.668   3.041   0.264  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.910   2.281   0.404  1.00  0.00           H  
HETATM   19  H4  UNL     1       4.586   0.447   0.423  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.763  -1.928   0.191  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.439  -2.392  -0.040  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.364  -2.777  -0.220  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.738  -3.126  -0.447  1.00  0.00           H  
HETATM   24  H9  UNL     1      -4.313  -1.271  -0.456  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.482   1.013  -0.229  1.00  0.00           H  
CONECT    1    2   16
CONECT    2    3    3   15
CONECT    3    4   17
CONECT    4    5    5    9
CONECT    5    6   18
CONECT    6    7    7   19
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10
CONECT   10   11   11   15
CONECT   11   12   22
CONECT   12   13   13   23
CONECT   13   14   24
CONECT   14   15   15   25
END
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SMILES for HMDB0059801 (9-Hydroxyphenanthrene)

OC1=CC2=CC=CC=C2C2=CC=CC=C12
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INCHI for HMDB0059801 (9-Hydroxyphenanthrene)

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
ValueSource
9-PhenanthrenolChEBI
9-PhenanthrolKegg
9-HydroxyphenanthreneChEBI
Chemical FormulaC14H10O
Average Molecular Weight194.2286
Monoisotopic Molecular Weight194.073164942
IUPAC Namephenanthren-9-ol
Traditional Name9-phenanthrol
CAS Registry NumberNot 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 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
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.00053 umol/mmol creatinineAdult (>18 years old)MaleRoofers (post shift) details
UrineDetected and Quantified0.000095-0.00102 umol/mmol creatinineAdult (>18 years old)MaleWorkers in coking plants details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11430
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenanthrenoid
METLIN IDNot Available
PubChem Compound10229
PDB IDNot Available
ChEBI ID28820
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]