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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:58:44 UTC

Update Date

2021-09-14 15:02:27 UTC

HMDB ID

HMDB0060776

Secondary Accession Numbers

HMDB60776

Metabolite Identification

Common Name

5-Hydroxydantrolene

Description

5-Hydroxydantrolene 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. 5-Hydroxydantrolene is a metabolite of dantrolene. 5-Hydroxydantrolene is an extremely weak basic (essentially neutral) compound (based on its pKa). Dantrolene sodium is a muscle relaxant that acts by abolishing excitation-contraction coupling in muscle cells, probably by action on the ryanodine receptor. It is the only specific and effective treatment for malignant hyperthermia, a rare, life-threatening disorder triggered by general anesthesia.

Structure

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

HMDB0060776
     RDKit          3D
5-Hydroxydantrolene
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.4267    2.5168   -1.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7417    1.2875   -1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9986    0.7232   -1.4473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9630   -0.5554   -1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0614   -1.3489   -1.7562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6271   -1.0040   -1.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7320   -1.7505    0.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591    0.1980   -0.8833 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072    0.2024   -0.5228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1045    0.3113    0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6675    0.3125    1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2005    0.4268    2.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1717    0.3869    2.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862    0.2511    0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8445    0.1696    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    0.2263    1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291    0.1462    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4605    0.0103   -0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7937   -0.0672   -1.1455 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.0607   -0.1896   -2.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8452   -0.0061   -0.2698 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.3634   -0.0456   -1.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879    0.0333   -0.9689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3519    0.2128    0.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9714   -1.1671   -1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349   -1.6292   -1.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4456   -1.3991    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8663    0.4019    1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8016    0.5291    3.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296    0.4543    3.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    0.3337    2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1056    0.1891    1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299   -0.1521   -2.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008   -0.0083   -1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  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
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  2  0
 14 24  1  0
  8  2  1  0
 24 11  1  0
 23 15  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 17 32  1  0
 22 33  1  0
 23 34  1  0
M  CHG  2  19   1  21  -1
M  END


  Mrv0541 07041311582D          

 24 26  0  0  0  0            999 V2000
   -0.6078    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1141   -1.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1940   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8841   -0.4005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4490   -1.8525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3690   -1.0679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    5.5902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815   -3.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295   -2.1075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6789   -0.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  5  1  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 13 12  1  0  0  0  0
 15  7  2  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  9  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 22 18  2  0  0  0  0
 23 18  2  0  0  0  0
 24 10  1  0  0  0  0
 24 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060776

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1N(\N=C\C2=CC=C(O2)C2=CC=C(C=C2)N(=O)=O)C(=O)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H10N4O6/c19-12-13(20)17(14(21)16-12)15-7-10-5-6-11(24-10)8-1-3-9(4-2-8)18(22)23/h1-7,13,20H,(H,16,19,21)/b15-7+

> <INCHI_KEY>
PGORTQZSSAZLCK-VIZOYTHASA-N

> <FORMULA>
C14H10N4O6

> <MOLECULAR_WEIGHT>
330.2524

> <EXACT_MASS>
330.060034072

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
30.853164052985875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dihydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]-2,5-dihydro-1H-imidazol-2-one

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
1.3352466019999998

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.832510800942034

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5037832032261034

> <JCHEM_PKA_STRONGEST_BASIC>
-1.966374300947884

> <JCHEM_POLAR_SURFACE_AREA>
144.45

> <JCHEM_REFRACTIVITY>
80.39459999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]-5H-imidazol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060776
     RDKit          3D
5-Hydroxydantrolene
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.4267    2.5168   -1.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7417    1.2875   -1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9986    0.7232   -1.4473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9630   -0.5554   -1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0614   -1.3489   -1.7562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6271   -1.0040   -1.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7320   -1.7505    0.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591    0.1980   -0.8833 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072    0.2024   -0.5228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1045    0.3113    0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6675    0.3125    1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2005    0.4268    2.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1717    0.3869    2.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862    0.2511    0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8445    0.1696    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    0.2263    1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291    0.1462    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4605    0.0103   -0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7937   -0.0672   -1.1455 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.0607   -0.1896   -2.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8452   -0.0061   -0.2698 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.3634   -0.0456   -1.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879    0.0333   -0.9689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3519    0.2128    0.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9714   -1.1671   -1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349   -1.6292   -1.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4456   -1.3991    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8663    0.4019    1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8016    0.5291    3.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296    0.4543    3.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    0.3337    2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1056    0.1891    1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299   -0.1521   -2.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008   -0.0083   -1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  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
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  2  0
 14 24  1  0
  8  2  1  0
 24 11  1  0
 23 15  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 17 32  1  0
 22 33  1  0
 23 34  1  0
M  CHG  2  19   1  21  -1
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0      -1.135   6.585   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.802   6.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.135   8.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.802   8.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.698   1.905   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.222   3.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.143   0.659   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.468   5.815   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.468   8.895   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.238   1.905   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.468   4.275   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.192  -4.363   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.946  -3.458   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.962  -1.993   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -3.517  -0.748   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -6.438  -3.458   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -4.422  -1.993   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -2.468  10.435   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -5.192  -5.903   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.482  -3.934   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.867  -0.748   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -3.802  11.205   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.135  11.205   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.714   3.370   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5    6   10                                                       
CONECT    6    5   11                                                       
CONECT    7   10   15                                                       
CONECT    8    1    2   11                                                  
CONECT    9    3    4   18                                                  
CONECT   10    5    7   24                                                  
CONECT   11    6    8   24                                                  
CONECT   12   13   16   19                                                  
CONECT   13   12   17   20                                                  
CONECT   14   16   17   21                                                  
CONECT   15    7   17                                                       
CONECT   16   12   14                                                       
CONECT   17   13   14   15                                                  
CONECT   18    9   22   23                                                  
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   18                                                            
CONECT   23   18                                                            
CONECT   24   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0060776
HETATM    1  O1  UNL     1      -4.427   2.517  -1.006  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.742   1.288  -1.105  1.00  0.00           C  
HETATM    3  N1  UNL     1      -5.999   0.723  -1.447  1.00  0.00           N  
HETATM    4  C2  UNL     1      -5.963  -0.555  -1.454  1.00  0.00           C  
HETATM    5  O2  UNL     1      -7.061  -1.349  -1.756  1.00  0.00           O  
HETATM    6  C3  UNL     1      -4.627  -1.004  -1.103  1.00  0.00           C  
HETATM    7  O3  UNL     1      -4.732  -1.751   0.090  1.00  0.00           O  
HETATM    8  N2  UNL     1      -3.859   0.198  -0.883  1.00  0.00           N  
HETATM    9  N3  UNL     1      -2.507   0.202  -0.523  1.00  0.00           N  
HETATM   10  C4  UNL     1      -2.104   0.311   0.698  1.00  0.00           C  
HETATM   11  C5  UNL     1      -0.667   0.312   1.045  1.00  0.00           C  
HETATM   12  C6  UNL     1      -0.200   0.427   2.336  1.00  0.00           C  
HETATM   13  C7  UNL     1       1.172   0.387   2.243  1.00  0.00           C  
HETATM   14  C8  UNL     1       1.486   0.251   0.911  1.00  0.00           C  
HETATM   15  C9  UNL     1       2.844   0.170   0.384  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.935   0.226   1.225  1.00  0.00           C  
HETATM   17  C11 UNL     1       5.229   0.146   0.698  1.00  0.00           C  
HETATM   18  C12 UNL     1       5.460   0.010  -0.654  1.00  0.00           C  
HETATM   19  N4  UNL     1       6.794  -0.067  -1.145  1.00  0.00           N1+
HETATM   20  O4  UNL     1       7.061  -0.190  -2.349  1.00  0.00           O  
HETATM   21  O5  UNL     1       7.845  -0.006  -0.270  1.00  0.00           O1-
HETATM   22  C13 UNL     1       4.363  -0.046  -1.488  1.00  0.00           C  
HETATM   23  C14 UNL     1       3.088   0.033  -0.969  1.00  0.00           C  
HETATM   24  O6  UNL     1       0.352   0.213   0.251  1.00  0.00           O  
HETATM   25  H1  UNL     1      -7.971  -1.167  -1.334  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.135  -1.629  -1.874  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.446  -1.399   0.680  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.866   0.402   1.458  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.802   0.529   3.254  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.830   0.454   3.093  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.814   0.334   2.307  1.00  0.00           H  
HETATM   32  H8  UNL     1       6.106   0.189   1.345  1.00  0.00           H  
HETATM   33  H9  UNL     1       4.530  -0.152  -2.551  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.201  -0.008  -1.605  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4    4
CONECT    4    5    6
CONECT    5   25
CONECT    6    7    8   26
CONECT    7   27
CONECT    8    9
CONECT    9   10   10
CONECT   10   11   28
CONECT   11   12   12   24
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   24
CONECT   15   16   16   23
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19   22
CONECT   19   20   20   21
CONECT   22   23   23   33
CONECT   23   34
END

HMDB0060776
     RDKit          3D
5-Hydroxydantrolene
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.4267    2.5168   -1.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7417    1.2875   -1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9986    0.7232   -1.4473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9630   -0.5554   -1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0614   -1.3489   -1.7562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6271   -1.0040   -1.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7320   -1.7505    0.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591    0.1980   -0.8833 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072    0.2024   -0.5228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1045    0.3113    0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6675    0.3125    1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2005    0.4268    2.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1717    0.3869    2.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862    0.2511    0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8445    0.1696    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    0.2263    1.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291    0.1462    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4605    0.0103   -0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7937   -0.0672   -1.1455 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.0607   -0.1896   -2.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8452   -0.0061   -0.2698 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.3634   -0.0456   -1.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879    0.0333   -0.9689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3519    0.2128    0.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9714   -1.1671   -1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349   -1.6292   -1.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4456   -1.3991    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8663    0.4019    1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8016    0.5291    3.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296    0.4543    3.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    0.3337    2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1056    0.1891    1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299   -0.1521   -2.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2008   -0.0083   -1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  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
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  2  0
 14 24  1  0
  8  2  1  0
 24 11  1  0
 23 15  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 17 32  1  0
 22 33  1  0
 23 34  1  0
M  CHG  2  19   1  21  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₀N₄O₆

Average Molecular Weight

330.2524

Monoisotopic Molecular Weight

330.060034072

IUPAC Name

4,5-dihydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]-2,5-dihydro-1H-imidazol-2-one

Traditional Name

4,5-dihydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]-5H-imidazol-2-one

CAS Registry Number

Not Available

SMILES

OC1N(\N=C\C2=CC=C(O2)C2=CC=C(C=C2)N(=O)=O)C(=O)N=C1O

InChI Identifier

InChI=1S/C14H10N4O6/c19-12-13(20)17(14(21)16-12)15-7-10-5-6-11(24-10)8-1-3-9(4-2-8)18(22)23/h1-7,13,20H,(H,16,19,21)/b15-7+

InChI Key

PGORTQZSSAZLCK-VIZOYTHASA-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
Alkanolamine
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
Organic oxide
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic zwitterion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060776)

Organ

Kidney (HMDB: HMDB0060776)
Liver (HMDB: HMDB0060776)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060776)

Cellular substructure

Cytoplasm (HMDB: HMDB0060776)

Source

Endogenous

Endogenous (HMDB: HMDB0060776)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.065 g/L	ALOGPS
logP	1.11	ALOGPS
logP	1.34	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	144.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.39 m³·mol⁻¹	ChemAxon
Polarizability	30.85 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
DeepCCS	[M+H]+	167.124	30932474
DeepCCS	[M-H]-	164.766	30932474
DeepCCS	[M-2H]-	199.057	30932474
DeepCCS	[M+Na]+	174.101	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.0	32859911
AllCCS	[M+NH4]+	177.5	32859911
AllCCS	[M+Na]+	178.4	32859911
AllCCS	[M-H]-	173.6	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	172.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.69 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9508 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1815.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	311.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	147.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	197.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	118.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	316.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	476.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	147.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1082.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	479.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1131.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	300.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	420.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	242.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	103.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxydantrolene	OC1N(\N=C\C2=CC=C(O2)C2=CC=C(C=C2)N(=O)=O)C(=O)N=C1O	4045.6	Standard polar	33892256
5-Hydroxydantrolene	OC1N(\N=C\C2=CC=C(O2)C2=CC=C(C=C2)N(=O)=O)C(=O)N=C1O	3196.1	Standard non polar	33892256
5-Hydroxydantrolene	OC1N(\N=C\C2=CC=C(O2)C2=CC=C(C=C2)N(=O)=O)C(=O)N=C1O	3329.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxydantrolene,1TMS,isomer #1	C[Si](C)(C)OC1C(O)=NC(=O)N1/N=C/C1=CC=C(C2=CC=C([N+](=O)[O-])C=C2)O1	3416.7	Semi standard non polar	33892256
5-Hydroxydantrolene,1TMS,isomer #2	C[Si](C)(C)OC1=NC(=O)N(/N=C/C2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1O	3412.6	Semi standard non polar	33892256
5-Hydroxydantrolene,2TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)N(/N=C/C2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1O[Si](C)(C)C	3369.5	Semi standard non polar	33892256
5-Hydroxydantrolene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(O)=NC(=O)N1/N=C/C1=CC=C(C2=CC=C([N+](=O)[O-])C=C2)O1	3663.3	Semi standard non polar	33892256
5-Hydroxydantrolene,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(=O)N(/N=C/C2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1O	3687.7	Semi standard non polar	33892256
5-Hydroxydantrolene,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=O)N(/N=C/C2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1O[Si](C)(C)C(C)(C)C	3842.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxydantrolene GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-6794000000-8cf2ef9b3183bca31ca8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxydantrolene GC-MS (2 TMS) - 70eV, Positive	splash10-0nti-6542900000-861630727116de99c14f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxydantrolene 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 10V, Positive-QTOF	splash10-001i-2109000000-ead47501e0cc8c67b0ab	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 20V, Positive-QTOF	splash10-02u0-1659000000-04f786f95110694331a0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 40V, Positive-QTOF	splash10-0006-9200000000-a50bdbd9a003516239e9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 10V, Negative-QTOF	splash10-0006-9213000000-92952110231970fb2111	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 20V, Negative-QTOF	splash10-0006-9001000000-672a8e2bb6f69b6123dc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 40V, Negative-QTOF	splash10-0006-9000000000-12c0ca375ddffe52ea9c	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9577331

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for 5-Hydroxydantrolene (HMDB0060776)

MOL for HMDB0060776 (5-Hydroxydantrolene)

3D MOL for HMDB0060776 (5-Hydroxydantrolene)

3D SDF for HMDB0060776 (5-Hydroxydantrolene)

3D-SDF for HMDB0060776 (5-Hydroxydantrolene)

PDB for HMDB0060776 (5-Hydroxydantrolene)

3D PDB for HMDB0060776 (5-Hydroxydantrolene)

SMILES for HMDB0060776 (5-Hydroxydantrolene)

INCHI for HMDB0060776 (5-Hydroxydantrolene)

Structure for HMDB0060776 (5-Hydroxydantrolene)

3D Structure for HMDB0060776 (5-Hydroxydantrolene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra