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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:57 UTC

HMDB ID

HMDB0015350

Secondary Accession Numbers

HMDB15350

Metabolite Identification

Common Name

Dantrolene

Description

Dantrolene is only found in individuals that have used or taken this drug.Chemically, dantrolene is a hydantoin derivative, but does not exhibit antiepileptic activity like other hydantoin derivates such as phenytoin.Dantrolene depresses excitation-contraction coupling in skeletal muscle by binding to the ryanodine receptor 1, and decreasing intracellular calcium concentration. Ryanodine receptors mediate the release of calcium from the sarcoplasmic reticulum, an essential step in muscle contraction.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0015350
     RDKit          3D
Dantrolene
 33 35  0  0  0  0  0  0  0  0999 V2000
   -7.3646    0.4074    0.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3041   -0.2869    0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0097    0.1828    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448   -0.7645    0.4793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6874   -0.5057    0.3436 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2895    0.5005   -0.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738    0.8175   -0.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4144    1.8855   -1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    1.8226   -1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2854    0.7324   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6613    0.3179   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525    1.0217   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0511    0.6594   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2872   -0.4450    0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6298   -0.8406    0.9024 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.6056   -0.1940    0.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8836   -1.9387    1.6860 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.1964   -1.1487    1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982   -0.7866    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675    0.1777   -0.0398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7587   -1.9531    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2713   -3.0953   -0.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1572   -1.6625    0.1542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617    1.1754    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9903    0.2506    2.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346    1.1232   -0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0105    2.6328   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715    2.5014   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5554    1.8938   -1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9107    1.2109   -0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3717   -2.0276    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0366   -1.3401    1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9528   -2.3243   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  2  0
 10 20  1  0
  4 21  1  0
 21 22  2  0
 21 23  1  0
 23  2  1  0
 20  7  1  0
 19 11  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 18 31  1  0
 19 32  1  0
 23 33  1  0
M  CHG  2  15   1  17  -1
M  END

  Mrv0541 04191212172D          

 23 25  0  0  0  0            999 V2000
    9.7382   -9.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5632   -9.8080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4833   -9.0233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8276  -10.0852    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.8182   -9.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9661   -9.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1507   -8.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6987   -8.7684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6335   -9.5504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2210   -8.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3010   -9.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0856   -9.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6122   -9.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0460   -8.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2145   -9.5332    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.1814   -9.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561  -10.8923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2533  -10.4754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6028   -8.7684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2253  -10.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7837   -9.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0099  -10.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5683   -8.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
 18  1  2  0  0  0  0
  5  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  3  1  4  0  0  0
 13  4  1  0  0  0  0
 15  4  1  0  0  0  0
 17  4  2  0  0  0  0
 19  5  2  0  0  0  0
  7  5  1  0  0  0  0
  9  6  1  0  0  0  0
 16  6  1  0  0  0  0
 10  6  2  0  0  0  0
 12  8  2  0  0  0  0
 11  9  1  0  0  0  0
 14 10  1  0  0  0  0
 12 11  1  0  0  0  0
 14 11  2  0  0  0  0
 21 13  2  0  0  0  0
 20 13  1  0  0  0  0
 22 16  1  0  0  0  0
 23 16  2  0  0  0  0
 22 20  2  0  0  0  0
 23 21  1  0  0  0  0
M  CHG  2   4   1  15  -1
M  END
> <DATABASE_ID>
HMDB0015350

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-][N+](=O)C1=CC=C(C=C1)C1=CC=C(O1)C=NN1CC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H10N4O5/c19-13-8-17(14(20)16-13)15-7-11-5-6-12(23-11)9-1-3-10(4-2-9)18(21)22/h1-7H,8H2,(H,16,19,20)

> <INCHI_KEY>
OZOMQRBLCMDCEG-UHFFFAOYSA-N

> <FORMULA>
C14H10N4O5

> <MOLECULAR_WEIGHT>
314.253

> <EXACT_MASS>
314.06511945

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.984830848970606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-({[5-(4-nitrophenyl)furan-2-yl]methylidene}amino)imidazolidine-2,4-dione

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.256485484666666

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.889167005716253

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.233154620304278

> <JCHEM_PKA_STRONGEST_BASIC>
-1.376752956749463

> <JCHEM_POLAR_SURFACE_AREA>
120.72999999999999

> <JCHEM_REFRACTIVITY>
78.87450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sodium, dantrolene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015350
     RDKit          3D
Dantrolene
 33 35  0  0  0  0  0  0  0  0999 V2000
   -7.3646    0.4074    0.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3041   -0.2869    0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0097    0.1828    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448   -0.7645    0.4793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6874   -0.5057    0.3436 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2895    0.5005   -0.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738    0.8175   -0.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4144    1.8855   -1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    1.8226   -1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2854    0.7324   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6613    0.3179   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525    1.0217   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0511    0.6594   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2872   -0.4450    0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6298   -0.8406    0.9024 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.6056   -0.1940    0.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8836   -1.9387    1.6860 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.1964   -1.1487    1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982   -0.7866    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675    0.1777   -0.0398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7587   -1.9531    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2713   -3.0953   -0.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1572   -1.6625    0.1542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617    1.1754    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9903    0.2506    2.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346    1.1232   -0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0105    2.6328   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715    2.5014   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5554    1.8938   -1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9107    1.2109   -0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3717   -2.0276    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0366   -1.3401    1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9528   -2.3243   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  2  0
 10 20  1  0
  4 21  1  0
 21 22  2  0
 21 23  1  0
 23  2  1  0
 20  7  1  0
 19 11  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 18 31  1  0
 19 32  1  0
 23 33  1  0
M  CHG  2  15   1  17  -1
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      18.178 -18.308   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      19.718 -18.308   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      17.702 -16.843   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.278 -18.826   0.000  0.00  0.00           N+1
HETATM    5  C   UNK     0      20.194 -16.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.137 -16.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.948 -15.938   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      16.238 -16.368   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      12.383 -17.827   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.613 -15.457   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.629 -16.922   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.093 -17.398   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.743 -18.350   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.153 -15.457   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.134 -17.795   0.000  0.00  0.00           O-1
HETATM   16  C   UNK     0       9.672 -17.398   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.958 -20.332   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      17.273 -19.554   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      21.659 -16.368   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.887 -19.380   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.063 -16.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.352 -18.904   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.527 -16.368   0.000  0.00  0.00           C+0
CONECT    1    2    3   18                                                  
CONECT    2    1    5                                                       
CONECT    3    1    7    8                                                  
CONECT    4   13   15   17                                                  
CONECT    5    2   19    7                                                  
CONECT    6    9   16   10                                                  
CONECT    7    3    5                                                       
CONECT    8    3   12                                                       
CONECT    9    6   11                                                       
CONECT   10    6   14                                                       
CONECT   11    9   12   14                                                  
CONECT   12    8   11                                                       
CONECT   13    4   21   20                                                  
CONECT   14   10   11                                                       
CONECT   15    4                                                            
CONECT   16    6   22   23                                                  
CONECT   17    4                                                            
CONECT   18    1                                                            
CONECT   19    5                                                            
CONECT   20   13   22                                                       
CONECT   21   13   23                                                       
CONECT   22   16   20                                                       
CONECT   23   16   21                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0015350
HETATM    1  O1  UNL     1      -7.365   0.407   0.304  1.00  0.00           O  
HETATM    2  C1  UNL     1      -6.304  -0.287   0.461  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.010   0.183   0.989  1.00  0.00           C  
HETATM    4  N1  UNL     1      -4.045  -0.765   0.479  1.00  0.00           N  
HETATM    5  N2  UNL     1      -2.687  -0.506   0.344  1.00  0.00           N  
HETATM    6  C3  UNL     1      -2.289   0.500  -0.353  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.874   0.818  -0.527  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.414   1.885  -1.265  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.961   1.823  -1.173  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.285   0.732  -0.393  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.661   0.318  -0.052  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.752   1.022  -0.511  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.051   0.659  -0.211  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.287  -0.445   0.577  1.00  0.00           C  
HETATM   15  N3  UNL     1       6.630  -0.841   0.902  1.00  0.00           N1+
HETATM   16  O2  UNL     1       7.606  -0.194   0.480  1.00  0.00           O  
HETATM   17  O3  UNL     1       6.884  -1.939   1.686  1.00  0.00           O1-
HETATM   18  C12 UNL     1       4.196  -1.149   1.036  1.00  0.00           C  
HETATM   19  C13 UNL     1       2.898  -0.787   0.735  1.00  0.00           C  
HETATM   20  O4  UNL     1       0.168   0.178  -0.040  1.00  0.00           O  
HETATM   21  C14 UNL     1      -4.759  -1.953   0.167  1.00  0.00           C  
HETATM   22  O5  UNL     1      -4.271  -3.095  -0.067  1.00  0.00           O  
HETATM   23  N4  UNL     1      -6.157  -1.663   0.154  1.00  0.00           N  
HETATM   24  H1  UNL     1      -4.762   1.175   0.531  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.990   0.251   2.095  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.035   1.123  -0.818  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.011   2.633  -1.813  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.671   2.501  -1.628  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.555   1.894  -1.134  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.911   1.211  -0.570  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.372  -2.028   1.662  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.037  -1.340   1.096  1.00  0.00           H  
HETATM   33  H10 UNL     1      -6.953  -2.324  -0.042  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   23
CONECT    3    4   24   25
CONECT    4    5   21
CONECT    5    6    6
CONECT    6    7   26
CONECT    7    8    8   20
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   20
CONECT   11   12   12   19
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   18
CONECT   15   16   16   17
CONECT   18   19   19   31
CONECT   19   32
CONECT   21   22   22   23
CONECT   23   33
END

HMDB0015350
     RDKit          3D
Dantrolene
 33 35  0  0  0  0  0  0  0  0999 V2000
   -7.3646    0.4074    0.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3041   -0.2869    0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0097    0.1828    0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448   -0.7645    0.4793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6874   -0.5057    0.3436 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2895    0.5005   -0.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8738    0.8175   -0.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4144    1.8855   -1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    1.8226   -1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2854    0.7324   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6613    0.3179   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525    1.0217   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0511    0.6594   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2872   -0.4450    0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6298   -0.8406    0.9024 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.6056   -0.1940    0.4799 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8836   -1.9387    1.6860 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.1964   -1.1487    1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982   -0.7866    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1675    0.1777   -0.0398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7587   -1.9531    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2713   -3.0953   -0.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1572   -1.6625    0.1542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617    1.1754    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9903    0.2506    2.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346    1.1232   -0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0105    2.6328   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715    2.5014   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5554    1.8938   -1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9107    1.2109   -0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3717   -2.0276    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0366   -1.3401    1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9528   -2.3243   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  2  0
 10 20  1  0
  4 21  1  0
 21 22  2  0
 21 23  1  0
 23  2  1  0
 20  7  1  0
 19 11  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 18 31  1  0
 19 32  1  0
 23 33  1  0
M  CHG  2  15   1  17  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-((5-(p-Nitrophenyl)furfurylidene)amino)hydantoin	ChEBI
Dantroleno	ChEBI
Dantrolenum	ChEBI

Chemical Formula

C₁₄H₁₀N₄O₅

Average Molecular Weight

314.253

Monoisotopic Molecular Weight

314.06511945

IUPAC Name

1-({[5-(4-nitrophenyl)furan-2-yl]methylidene}amino)imidazolidine-2,4-dione

Traditional Name

sodium, dantrolene

CAS Registry Number

7261-97-4

SMILES

[O-][N+](=O)C1=CC=C(C=C1)C1=CC=C(O1)C=NN1CC(=O)NC1=O

InChI Identifier

InChI=1S/C14H10N4O5/c19-13-8-17(14(20)16-13)15-7-11-5-6-12(23-11)9-1-3-10(4-2-9)18(21)22/h1-7H,8H2,(H,16,19,20)

InChI Key

OZOMQRBLCMDCEG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Hydantoins

Alternative Parents

Substituents

Hydantoin
Alpha-amino acid or derivatives
Nitrobenzene
Nitroaromatic compound
Monocyclic benzene moiety
Semicarbazone
Benzenoid
Heteroaromatic compound
Dicarboximide
Furan
Semicarbazide
Organic nitro compound
C-nitro compound
Carbonic acid derivative
Oxacycle
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic zwitterion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

hydrazone (CHEBI:4317 )
imidazolidine-2,4-dione (CHEBI:4317 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015350)

Source

Exogenous

Exogenous (HMDB: HMDB0015350)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	279 - 280 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.08 g/L	Not Available
LogP	1.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.08 g/L	ALOGPS
logP	1.65	ALOGPS
logP	1.26	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.23	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	120.73 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.87 m³·mol⁻¹	ChemAxon
Polarizability	29.98 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.481	31661259
DarkChem	[M-H]-	173.365	31661259
DeepCCS	[M+H]+	174.102	30932474
DeepCCS	[M-H]-	171.744	30932474
DeepCCS	[M-2H]-	205.256	30932474
DeepCCS	[M+Na]+	180.484	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.8	32859911
AllCCS	[M-H]-	171.1	32859911
AllCCS	[M+Na-2H]-	170.4	32859911
AllCCS	[M+HCOO]-	169.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dantrolene	[O-][N+](=O)C1=CC=C(C=C1)C1=CC=C(O1)C=NN1CC(=O)NC1=O	3998.0	Standard polar	33892256
Dantrolene	[O-][N+](=O)C1=CC=C(C=C1)C1=CC=C(O1)C=NN1CC(=O)NC1=O	2870.3	Standard non polar	33892256
Dantrolene	[O-][N+](=O)C1=CC=C(C=C1)C1=CC=C(O1)C=NN1CC(=O)NC1=O	3323.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dantrolene,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O	3253.9	Semi standard non polar	33892256
Dantrolene,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O	3208.6	Standard non polar	33892256
Dantrolene,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O	4710.8	Standard polar	33892256
Dantrolene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O	3550.3	Semi standard non polar	33892256
Dantrolene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O	3432.6	Standard non polar	33892256
Dantrolene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O	4600.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dantrolene GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-1690000000-d26c38a9d976493f22ba	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dantrolene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dantrolene 15V, Negative-QTOF	splash10-03di-0049000000-a19e7d4f9959ab10cf89	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dantrolene 30V, Negative-QTOF	splash10-0udi-0090000000-22c70ff1c5c85bfa53de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dantrolene 60V, Negative-QTOF	splash10-0002-1920000000-858f043b14cd350ebe7b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dantrolene 45V, Negative-QTOF	splash10-0udi-1590000000-dbed64771a911370b0ec	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dantrolene 90V, Negative-QTOF	splash10-0002-1900000000-e90a3c39335b51d5ed54	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dantrolene 75V, Negative-QTOF	splash10-0002-1900000000-bfa08bf4fe11a1397edc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dantrolene 60V, Positive-QTOF	splash10-0002-1910000000-2c36c4de7fa561e975cc	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dantrolene 10V, Positive-QTOF	splash10-014i-0019000000-2fc8ae4177ccb56abfab	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dantrolene 20V, Positive-QTOF	splash10-014i-0149000000-a112fe650fdea6c2b688	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dantrolene 40V, Positive-QTOF	splash10-0002-9650000000-76571330cab68a28e44e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dantrolene 10V, Negative-QTOF	splash10-03di-2009000000-2b189b79919d98a46bdb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dantrolene 20V, Negative-QTOF	splash10-0006-9000000000-84778de90459e0d43216	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dantrolene 40V, Negative-QTOF	splash10-0006-9000000000-3874c10b014fca6acc21	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01219	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01219	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01219

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5290202

KEGG Compound ID

C06939

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dantrolene

METLIN ID

Not Available

PubChem Compound

6914273

PDB ID

Not Available

ChEBI ID

4317

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Krause T, Gerbershagen MU, Fiege M, Weisshorn R, Wappler F: Dantrolene--a review of its pharmacology, therapeutic use and new developments. Anaesthesia. 2004 Apr;59(4):364-73. [PubMed:15023108 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Ryanodine receptor 1

General function:: Involved in calcium channel activity
Specific function:: Communication between transverse-tubules and sarcoplasmic reticulum. Contraction of skeletal muscle is triggered by release of calcium ions from SR following depolarization of T-tubules
Gene Name:: RYR1
Uniprot ID:: P21817
Molecular weight:: 565170.7

References

Britt BA, Scott E, Frodis W, Clements MJ, Endrenyi L: Dantrolene--in vitro studies in malignant hyperthermia susceptible (MHS) and normal skeletal muscle. Can Anaesth Soc J. 1984 Mar;31(2):130-54. [PubMed:6704779 ]
Harrison GG: Control of the malignant hyperpyrexic syndrome in MHS swine by dantrolene sodium. 1975. Br J Anaesth. 1998 Oct;81(4):626-9; discussion 625. [PubMed:9924249 ]
Flewellen EH, Nelson TE: Dantrolene dose response in malignant hyperthermia-susceptible (MHS) swine: method to obtain prophylaxis and therapeusis. Anesthesiology. 1980 Apr;52(4):303-8. [PubMed:7362049 ]
Tonner PH, Scholz J, Richter A, Loscher W, Steinfath M, Wappler F, Wlaz P, Hadji B, Roewer N, Schulte am Esch J: Alterations of inositol polyphosphates in skeletal muscle during porcine malignant hyperthermia. Br J Anaesth. 1995 Oct;75(4):467-71. [PubMed:7488490 ]
Zhao X, Weisleder N, Han X, Pan Z, Parness J, Brotto M, Ma J: Azumolene inhibits a component of store-operated calcium entry coupled to the skeletal muscle ryanodine receptor. J Biol Chem. 2006 Nov 3;281(44):33477-86. Epub 2006 Aug 31. [PubMed:16945924 ]
Krause T, Gerbershagen MU, Fiege M, Weisshorn R, Wappler F: Dantrolene--a review of its pharmacology, therapeutic use and new developments. Anaesthesia. 2004 Apr;59(4):364-73. [PubMed:15023108 ]
Gerbershagen MU, Fiege M, Krause T, Agarwal K, Wappler F: [Dantrolene. Pharmacological and therapeutic aspects]. Anaesthesist. 2003 Mar;52(3):238-45. [PubMed:12666006 ]
Paul-Pletzer K, Yamamoto T, Bhat MB, Ma J, Ikemoto N, Jimenez LS, Morimoto H, Williams PG, Parness J: Identification of a dantrolene-binding sequence on the skeletal muscle ryanodine receptor. J Biol Chem. 2002 Sep 20;277(38):34918-23. Epub 2002 Jul 11. [PubMed:12167662 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Dantrolene (HMDB0015350)

MOL for HMDB0015350 (Dantrolene)

3D MOL for HMDB0015350 (Dantrolene)

3D SDF for HMDB0015350 (Dantrolene)

3D-SDF for HMDB0015350 (Dantrolene)

PDB for HMDB0015350 (Dantrolene)

3D PDB for HMDB0015350 (Dantrolene)

SMILES for HMDB0015350 (Dantrolene)

INCHI for HMDB0015350 (Dantrolene)

Structure for HMDB0015350 (Dantrolene)

3D Structure for HMDB0015350 (Dantrolene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References