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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014803

Secondary Accession Numbers

HMDB14803

Metabolite Identification

Common Name

Nilutamide

Description

Nilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration.

Structure

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

HMDB0014803
     RDKit          3D
Nilutamide
 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.1272   -0.3992   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    0.2167    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273    1.6339    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9453   -0.6269    1.1965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -0.8463    1.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.3560    2.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944   -0.4065    0.3779 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346   -0.4484    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3145   -1.5472    0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6791   -1.6734    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4468   -0.6393    0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8409   -0.7915   -0.0717 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.3201   -1.9580   -0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7236    0.2285   -0.0946 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.7786    0.4562   -0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5046    1.6026   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3465    2.2472   -0.1443 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    1.1549   -2.0640 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6132    2.4766   -1.6163 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3739    0.5555   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7194    0.1012   -0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    0.4116   -1.7944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2321    0.0704   -1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0624   -0.3648   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8650   -1.4949   -0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158    2.2425    0.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0562    2.0046   -0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637    1.6050    1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7616   -0.9994    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204   -2.3474    1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -2.5350    0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    1.4269   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  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
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 15 20  2  0
  7 21  1  0
 21 22  2  0
 21  2  1  0
 20  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  9 30  1  0
 10 31  1  0
 20 32  1  0
M  CHG  2  12   1  14  -1
M  END

665
  Mrv0541 02231214542D          

 22 23  0  0  0  0            999 V2000
    2.9685    1.7245    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    1.7245    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.5496    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6956   -2.1231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1477    0.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4870    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.3645    1.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.7505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -1.0281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8995    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.1157   -1.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3087   -1.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8302   -2.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9442   -2.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 22  1  0  0  0  0
  2 22  1  0  0  0  0
  3 22  1  0  0  0  0
  4 12  2  0  0  0  0
  5 15  2  0  0  0  0
  6 10  1  0  0  0  0
  7 10  2  0  0  0  0
  8 12  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  9 11  1  0  0  0  0
  9 15  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 21  2  0  0  0  0
 19 20  2  0  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
M  CHG  2   6  -1  10   1
M  END
> <DATABASE_ID>
HMDB0014803

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)

> <INCHI_KEY>
XWXYUMMDTVBTOU-UHFFFAOYSA-N

> <FORMULA>
C12H10F3N3O4

> <MOLECULAR_WEIGHT>
317.2207

> <EXACT_MASS>
317.062340438

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.875970933255005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
2.250776846

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.009375986356279

> <JCHEM_PKA_STRONGEST_BASIC>
-4.382029466418218

> <JCHEM_POLAR_SURFACE_AREA>
95.22999999999999

> <JCHEM_REFRACTIVITY>
68.22600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nilutamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014803
     RDKit          3D
Nilutamide
 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.1272   -0.3992   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    0.2167    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273    1.6339    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9453   -0.6269    1.1965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -0.8463    1.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.3560    2.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944   -0.4065    0.3779 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346   -0.4484    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3145   -1.5472    0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6791   -1.6734    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4468   -0.6393    0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8409   -0.7915   -0.0717 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.3201   -1.9580   -0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7236    0.2285   -0.0946 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.7786    0.4562   -0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5046    1.6026   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3465    2.2472   -0.1443 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    1.1549   -2.0640 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6132    2.4766   -1.6163 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3739    0.5555   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7194    0.1012   -0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    0.4116   -1.7944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2321    0.0704   -1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0624   -0.3648   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8650   -1.4949   -0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158    2.2425    0.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0562    2.0046   -0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637    1.6050    1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7616   -0.9994    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204   -2.3474    1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -2.5350    0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    1.4269   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  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
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 15 20  2  0
  7 21  1  0
 21 22  2  0
 21  2  1  0
 20  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  9 30  1  0
 10 31  1  0
 20 32  1  0
M  CHG  2  12   1  14  -1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 665                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       5.541   3.219   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       8.621   3.219   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       7.081   4.759   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0       8.765  -3.963   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.476   0.732   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.080   0.909   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0       4.414   3.219   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       9.748  -1.401   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      12.186  -1.919   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       4.414   1.679   0.000  0.00  0.00           N+1
HETATM   11  C   UNK     0      11.416  -3.253   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.910  -2.933   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.750  -4.023   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.096  -4.759   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.156  -0.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -0.631   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   0.909   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -1.401   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081   1.679   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.748   0.909   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.748  -0.631   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.081   3.219   0.000  0.00  0.00           C+0
CONECT    1   22                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4   12                                                            
CONECT    5   15                                                            
CONECT    6   10                                                            
CONECT    7   10                                                            
CONECT    8   12   15   16                                                  
CONECT    9   11   15                                                       
CONECT   10    6    7   20                                                  
CONECT   11    9   12   13   14                                             
CONECT   12    4    8   11                                                  
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    5    8    9                                                  
CONECT   16    8   17   18                                                  
CONECT   17   16   19                                                       
CONECT   18   16   21                                                       
CONECT   19   17   20   22                                                  
CONECT   20   10   19   21                                                  
CONECT   21   18   20                                                       
CONECT   22    1    2    3   19                                             
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0014803
HETATM    1  C1  UNL     1      -4.127  -0.399  -0.839  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.039   0.217   0.033  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.427   1.634   0.375  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.945  -0.627   1.196  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.586  -0.846   1.466  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.064  -1.356   2.506  1.00  0.00           O  
HETATM    7  N2  UNL     1      -0.794  -0.407   0.378  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.635  -0.448   0.248  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.315  -1.547   0.709  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.679  -1.673   0.625  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.447  -0.639   0.040  1.00  0.00           C  
HETATM   12  N3  UNL     1       4.841  -0.791  -0.072  1.00  0.00           N1+
HETATM   13  O2  UNL     1       5.320  -1.958  -0.158  1.00  0.00           O  
HETATM   14  O3  UNL     1       5.724   0.228  -0.095  1.00  0.00           O1-
HETATM   15  C9  UNL     1       2.779   0.456  -0.419  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.505   1.603  -1.019  1.00  0.00           C  
HETATM   17  F1  UNL     1       4.347   2.247  -0.144  1.00  0.00           F  
HETATM   18  F2  UNL     1       4.324   1.155  -2.064  1.00  0.00           F  
HETATM   19  F3  UNL     1       2.613   2.477  -1.616  1.00  0.00           F  
HETATM   20  C11 UNL     1       1.374   0.555  -0.318  1.00  0.00           C  
HETATM   21  C12 UNL     1      -1.719   0.101  -0.588  1.00  0.00           C  
HETATM   22  O4  UNL     1      -1.473   0.412  -1.794  1.00  0.00           O  
HETATM   23  H1  UNL     1      -4.232   0.070  -1.813  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.062  -0.365  -0.215  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.865  -1.495  -0.896  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.516   2.242   0.485  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.056   2.005  -0.473  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.064   1.605   1.272  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.762  -0.999   1.731  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.720  -2.347   1.163  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.217  -2.535   0.987  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.894   1.427  -0.690  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4   21
CONECT    3   26   27   28
CONECT    4    5   29
CONECT    5    6    6    7
CONECT    7    8   21
CONECT    8    9    9   20
CONECT    9   10   30
CONECT   10   11   11   31
CONECT   11   12   15
CONECT   12   13   13   14
CONECT   15   16   20   20
CONECT   16   17   18   19
CONECT   20   32
CONECT   21   22   22
END

HMDB0014803
     RDKit          3D
Nilutamide
 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.1272   -0.3992   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    0.2167    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4273    1.6339    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9453   -0.6269    1.1965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -0.8463    1.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.3560    2.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944   -0.4065    0.3779 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346   -0.4484    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3145   -1.5472    0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6791   -1.6734    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4468   -0.6393    0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8409   -0.7915   -0.0717 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.3201   -1.9580   -0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7236    0.2285   -0.0946 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.7786    0.4562   -0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5046    1.6026   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3465    2.2472   -0.1443 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    1.1549   -2.0640 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6132    2.4766   -1.6163 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3739    0.5555   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7194    0.1012   -0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    0.4116   -1.7944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2321    0.0704   -1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0624   -0.3648   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8650   -1.4949   -0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158    2.2425    0.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0562    2.0046   -0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637    1.6050    1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7616   -0.9994    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204   -2.3474    1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -2.5350    0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    1.4269   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  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
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 15 20  2  0
  7 21  1  0
 21 22  2  0
 21  2  1  0
 20  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  9 30  1  0
 10 31  1  0
 20 32  1  0
M  CHG  2  12   1  14  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,5-Dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoin	ChEBI
Nilandron	ChEBI
Nilutamida	ChEBI
Nilutamidum	ChEBI
5,5-Dimethyl-3-(a,a,a-trifluoro-4-nitro-m-tolyl)hydantoin	Generator
5,5-Dimethyl-3-(α,α,α-trifluoro-4-nitro-m-tolyl)hydantoin	Generator
5,5-Dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)- 2,4-imidazolidinedione	HMDB
Hoechst brand OF nilutamide	HMDB
Aventis behring brand OF nilutamide	HMDB
Aventis brand OF nilutamide	HMDB
Anandron	HMDB

Chemical Formula

C₁₂H₁₀F₃N₃O₄

Average Molecular Weight

317.2207

Monoisotopic Molecular Weight

317.062340438

IUPAC Name

5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione

Traditional Name

nilutamide

CAS Registry Number

63612-50-0

SMILES

CC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

InChI Identifier

InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)

InChI Key

XWXYUMMDTVBTOU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Phenylhydantoins

Alternative Parents

Substituents

3-phenylhydantoin
Phenylimidazolidine
Alpha-amino acid or derivatives
Trifluoromethylbenzene
Nitrobenzene
Nitroaromatic compound
N-acyl urea
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Organic nitro compound
C-nitro compound
Carbonic acid derivative
Urea
Azacycle
Organic 1,3-dipolar compound
Carboxylic acid derivative
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Carbonyl group
Organohalogen compound
Organic zwitterion
Organic oxygen compound
Hydrocarbon derivative
Alkyl fluoride
Organic nitrogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Alkyl halide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:7573 )
imidazolidinone (CHEBI:7573 )
(trifluoromethyl)benzenes (CHEBI:7573 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014803)
Membrane (HMDB: HMDB0014803)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0042 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	1.74	ALOGPS
logP	2.25	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	15.01	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	95.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.23 m³·mol⁻¹	ChemAxon
Polarizability	25.88 Å³	ChemAxon
Number of Rings	2	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]+	169.724	30932474
DeepCCS	[M-H]-	166.055	30932474
DeepCCS	[M-2H]-	202.184	30932474
DeepCCS	[M+Na]+	178.29	30932474
AllCCS	[M+H]+	165.4	32859911
AllCCS	[M+H-H2O]+	162.1	32859911
AllCCS	[M+NH4]+	168.4	32859911
AllCCS	[M+Na]+	169.3	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	163.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nilutamide	CC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F	2457.5	Standard polar	33892256
Nilutamide	CC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F	2253.6	Standard non polar	33892256
Nilutamide	CC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F	2159.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nilutamide,1TMS,isomer #1	CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C	2044.1	Semi standard non polar	33892256
Nilutamide,1TMS,isomer #1	CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C	2157.3	Standard non polar	33892256
Nilutamide,1TMS,isomer #1	CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C	2480.6	Standard polar	33892256
Nilutamide,1TBDMS,isomer #1	CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C(C)(C)C	2322.7	Semi standard non polar	33892256
Nilutamide,1TBDMS,isomer #1	CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C(C)(C)C	2357.6	Standard non polar	33892256
Nilutamide,1TBDMS,isomer #1	CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C(C)(C)C	2522.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nilutamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9051000000-b212093377487cffc158	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nilutamide 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 - Nilutamide 30V, Negative-QTOF	splash10-0600-0094000000-0991ece9f9d42b94c643	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nilutamide 15V, Negative-QTOF	splash10-014i-0019000000-7989a507a8031f03f612	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nilutamide 45V, Negative-QTOF	splash10-00di-0090000000-1d63c70e06fcd4c6d922	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nilutamide 60V, Negative-QTOF	splash10-0kmi-0390000000-05fc687a7f642e06e60a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nilutamide 60V, Positive-QTOF	splash10-0kmi-0390000000-e2d42b542bf6dc07d5c0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nilutamide 75V, Negative-QTOF	splash10-0zfr-1970000000-f1091bfdddddc602902c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nilutamide 90V, Negative-QTOF	splash10-0lz9-1920000000-14b04987997234218267	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nilutamide 10V, Positive-QTOF	splash10-014i-0009000000-f4acafe069c7fdcf8fc3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nilutamide 20V, Positive-QTOF	splash10-0a4i-9025000000-2c79c0bbfc87dd118bd7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nilutamide 40V, Positive-QTOF	splash10-0a4l-9000000000-a91f0e83aff94e2bad18	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nilutamide 10V, Negative-QTOF	splash10-014i-0009000000-19746ba07e5113297e15	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nilutamide 20V, Negative-QTOF	splash10-014i-4009000000-f2904499b324cc347c22	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nilutamide 40V, Negative-QTOF	splash10-0a4l-9000000000-740d06c64bdf821f7e3d	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB00665	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00665	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00665

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4337

KEGG Compound ID

C08164

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nilutamide

METLIN ID

Not Available

PubChem Compound

4493

PDB ID

Not Available

ChEBI ID

7573

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

Kassouf W, Tanguay S, Aprikian AG: Nilutamide as second line hormone therapy for prostate cancer after androgen ablation fails. J Urol. 2003 May;169(5):1742-4. [PubMed:12686822 ]
Lukka H, Waldron T, Klotz L, Winquist E, Trachtenberg J: Maximal androgen blockade for the treatment of metastatic prostate cancer--a systematic review. Curr Oncol. 2006 Jun;13(3):81-93. [PubMed:17576447 ]

Enzymes

Enzyme Details

1. NADPH--cytochrome P450 reductase

General function:: Involved in oxidoreductase activity
Specific function:: This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name:: POR
Uniprot ID:: P16435
Molecular weight:: 77047.575

References

Berger V, Berson A, Wolf C, Chachaty C, Fau D, Fromenty B, Pessayre D: Generation of free radicals during the reductive metabolism of nilutamide by lung microsomes: possible role in the development of lung lesions in patients treated with this anti-androgen. Biochem Pharmacol. 1992 Feb 4;43(3):654-7. [PubMed:1311586 ]

Enzyme Details

2. Cytochrome P450 2C9

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

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

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

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

4. Cytochrome P450 2C8

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

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

5. Androgen receptor

General function:: Involved in DNA binding
Specific function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:: AR
Uniprot ID:: P10275
Molecular weight:: 98987.9

References

Raynaud JP: Antiandrogens in combination with LH-RH agonists in prostate cancer. Am J Clin Oncol. 1988;11 Suppl 2:S132-47. [PubMed:3071951 ]
Moguilewsky M, Bertagna C, Hucher M: Pharmacological and clinical studies of the antiandrogen Anandron. J Steroid Biochem. 1987;27(4-6):871-5. [PubMed:3320565 ]
Raynaud JP, Bonne C, Moguilewsky M, Lefebvre FA, Belanger A, Labrie F: The pure antiandrogen RU 23908 (Anandron), a candidate of choice for the combined antihormonal treatment of prostatic cancer: a review. Prostate. 1984;5(3):299-311. [PubMed:6374639 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Labrie F: Hormonal therapy of prostate cancer. Prog Brain Res. 2010;182:321-41. doi: 10.1016/S0079-6123(10)82014-X. [PubMed:20541672 ]
Schasfoort EM, Van De Beek C, Newling DW: Safety and efficacy of a non-steroidal anti-androgen, based on results of a post marketing surveillance of nilutamide. Prostate Cancer Prostatic Dis. 2001;4(2):112-117. [PubMed:12497048 ]
Kaisary AV, Iversen P, Tyrrell CJ, Carroll K, Morris T: Is there a role for antiandrogen monotherapy in patients with metastatic prostate cancer? Prostate Cancer Prostatic Dis. 2001;4(4):196-203. [PubMed:12497018 ]
Kolvenbag GJ, Furr BJ, Blackledge GR: Receptor affinity and potency of non-steroidal antiandrogens: translation of preclinical findings into clinical activity. Prostate Cancer Prostatic Dis. 1998 Dec;1(6):307-314. [PubMed:12496872 ]
Brawer MK, Crawford ED, Labrie F, Mendoza-Valdes A, Miller PD, Petrylak DP: Androgen deprivation and other treatments for advanced prostate cancer. Rev Urol. 2001;3 Suppl 2:S59-68. [PubMed:16986000 ]

Showing metabocard for Nilutamide (HMDB0014803)

MOL for HMDB0014803 (Nilutamide)

3D MOL for HMDB0014803 (Nilutamide)

3D SDF for HMDB0014803 (Nilutamide)

3D-SDF for HMDB0014803 (Nilutamide)

PDB for HMDB0014803 (Nilutamide)

3D PDB for HMDB0014803 (Nilutamide)

SMILES for HMDB0014803 (Nilutamide)

INCHI for HMDB0014803 (Nilutamide)

Structure for HMDB0014803 (Nilutamide)

3D Structure for HMDB0014803 (Nilutamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References