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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:09:02 UTC

Update Date

2019-07-23 07:15:27 UTC

HMDB ID

HMDB0060949

Secondary Accession Numbers

HMDB60949

Metabolite Identification

Common Name

2-hydroxyflutamide

Description

2-hydroxyflutamide, also known as OH-flutamide, belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups. Antiandrogens alter the androgen pathway by blocking the appropriate receptors, competing for binding sites on the cell's surface, or affecting androgen production. Environmental antiandrogens can have harmful effects on reproductive organ development in fetuses exposed in utero as well as their offspring. 2-hydroxyflutamide is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-hydroxyflutamide is a potentially toxic compound. It competes with testosterone and its powerful metabolite, dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. Flutamide is an oral nonsteroidal antiandrogen drug primarily used to treat prostate cancer. 2-hydroxyflutamide is a metabolite of flutamide. Steroidal antiandrogens not only counter androgens, but also affect secondary sex characteristics.

Structure

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

HMDB0060949
     RDKit          3D
2-hydroxyflutamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -3.5663   -1.1115    1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0973   -0.4956   -0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0238    0.6274   -0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0751   -1.4782   -0.9925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -0.0499    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715    0.8872    1.1948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -0.4945   -0.4992 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6020   -0.0295   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398    1.3264   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1295    1.7278    0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083    0.8589    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229    1.3376    0.4646 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.3990    0.7304    1.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8576    2.5684   -0.0459 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.9701   -0.4972    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0390   -1.4966    0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0193   -1.2632   -0.7795 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935   -2.7359   -0.1749 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5534   -1.6777    1.4413 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -0.8959   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352   -2.0712    1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613   -1.2249    1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2071   -0.4354    2.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7460    0.8870    0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3710    1.5028   -0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5913    0.3234   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6893   -1.2640   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613    1.5921    1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0175    2.0234   -0.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226    2.7877    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -1.9595   -0.2553 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
  2  5  1  0
  5  6  1  0
  5  7  2  3
  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
 20  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 10 30  1  0
 20 31  1  0
M  CHG  2  12   1  14  -1
M  END


  Mrv0541 07091309092D          

 20 20  0  0  0  0            999 V2000
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.9520    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 11  1  0  0  0  0
 15  6  1  4  0  0  0
 15  9  2  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 16  2  0  0  0  0
 20 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060949

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(O)C(O)=NC1=CC(=C(C=C1)N(=O)=O)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17)

> <INCHI_KEY>
YPQLFJODEKMJEF-UHFFFAOYSA-N

> <FORMULA>
C11H11F3N2O4

> <MOLECULAR_WEIGHT>
292.2112

> <EXACT_MASS>
292.067091465

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
24.074176105718507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanimidic acid

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.940527607

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.496883951297477

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8013775499486147

> <JCHEM_PKA_STRONGEST_BASIC>
0.11898093474676885

> <JCHEM_POLAR_SURFACE_AREA>
98.63999999999999

> <JCHEM_REFRACTIVITY>
65.8839

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyflutamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060949
     RDKit          3D
2-hydroxyflutamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -3.5663   -1.1115    1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0973   -0.4956   -0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0238    0.6274   -0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0751   -1.4782   -0.9925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -0.0499    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715    0.8872    1.1948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -0.4945   -0.4992 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6020   -0.0295   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398    1.3264   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1295    1.7278    0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083    0.8589    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229    1.3376    0.4646 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.3990    0.7304    1.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8576    2.5684   -0.0459 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.9701   -0.4972    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0390   -1.4966    0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0193   -1.2632   -0.7795 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935   -2.7359   -0.1749 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5534   -1.6777    1.4413 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -0.8959   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352   -2.0712    1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613   -1.2249    1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2071   -0.4354    2.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7460    0.8870    0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3710    1.5028   -0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5913    0.3234   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6893   -1.2640   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613    1.5921    1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0175    2.0234   -0.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226    2.7877    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -1.9595   -0.2553 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
  2  5  1  0
  5  6  1  0
  5  7  2  3
  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
 20  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 10 30  1  0
 20 31  1  0
M  CHG  2  12   1  14  -1
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  F   UNK     0      -2.667   3.080   0.000  0.00  0.00           F+0
HETATM   13  F   UNK     0      -0.564   3.644   0.000  0.00  0.00           F+0
HETATM   14  F   UNK     0      -2.104   0.976   0.000  0.00  0.00           F+0
HETATM   15  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.540  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    4    6                                                       
CONECT    4    3    8                                                       
CONECT    5    6    7                                                       
CONECT    6    3    5   15                                                  
CONECT    7    5    8   11                                                  
CONECT    8    4    7   16                                                  
CONECT    9   10   15   17                                                  
CONECT   10    1    2    9   18                                             
CONECT   11    7   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    6    9                                                       
CONECT   16    8   19   20                                                  
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   16                                                            
CONECT   20   16                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0060949
HETATM    1  C1  UNL     1      -3.566  -1.111   1.299  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.097  -0.496  -0.006  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.024   0.627  -0.359  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.075  -1.478  -0.992  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.695  -0.050   0.199  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.472   0.887   1.195  1.00  0.00           O  
HETATM    7  N1  UNL     1      -0.717  -0.495  -0.499  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.602  -0.030  -0.256  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.840   1.326  -0.121  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.130   1.728   0.114  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.208   0.859   0.224  1.00  0.00           C  
HETATM   12  N2  UNL     1       4.523   1.338   0.465  1.00  0.00           N1+
HETATM   13  O3  UNL     1       5.399   0.730   1.103  1.00  0.00           O  
HETATM   14  O4  UNL     1       4.858   2.568  -0.046  1.00  0.00           O1-
HETATM   15  C9  UNL     1       2.970  -0.497   0.090  1.00  0.00           C  
HETATM   16  C10 UNL     1       4.039  -1.497   0.194  1.00  0.00           C  
HETATM   17  F1  UNL     1       5.019  -1.263  -0.780  1.00  0.00           F  
HETATM   18  F2  UNL     1       3.494  -2.736  -0.175  1.00  0.00           F  
HETATM   19  F3  UNL     1       4.553  -1.678   1.441  1.00  0.00           F  
HETATM   20  C11 UNL     1       1.667  -0.896  -0.147  1.00  0.00           C  
HETATM   21  H1  UNL     1      -3.035  -2.071   1.469  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.661  -1.225   1.334  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.207  -0.435   2.128  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.746   0.887   0.429  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.371   1.503  -0.645  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.591   0.323  -1.279  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.689  -1.264  -1.742  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.161   1.592   1.390  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.017   2.023  -0.203  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.323   2.788   0.220  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.467  -1.960  -0.255  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    5
CONECT    3   24   25   26
CONECT    4   27
CONECT    5    6    7    7
CONECT    6   28
CONECT    7    8
CONECT    8    9    9   20
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12   15
CONECT   12   13   13   14
CONECT   15   16   20   20
CONECT   16   17   18   19
CONECT   20   31
END

HMDB0060949
     RDKit          3D
2-hydroxyflutamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -3.5663   -1.1115    1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0973   -0.4956   -0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0238    0.6274   -0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0751   -1.4782   -0.9925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -0.0499    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715    0.8872    1.1948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -0.4945   -0.4992 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6020   -0.0295   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398    1.3264   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1295    1.7278    0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083    0.8589    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229    1.3376    0.4646 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.3990    0.7304    1.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8576    2.5684   -0.0459 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.9701   -0.4972    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0390   -1.4966    0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0193   -1.2632   -0.7795 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4935   -2.7359   -0.1749 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5534   -1.6777    1.4413 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -0.8959   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352   -2.0712    1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613   -1.2249    1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2071   -0.4354    2.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7460    0.8870    0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3710    1.5028   -0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5913    0.3234   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6893   -1.2640   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613    1.5921    1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0175    2.0234   -0.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226    2.7877    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -1.9595   -0.2553 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
  2  5  1  0
  5  6  1  0
  5  7  2  3
  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
 20  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 10 30  1  0
 20 31  1  0
M  CHG  2  12   1  14  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
OH-Flutamide	HMDB

Chemical Formula

C₁₁H₁₁F₃N₂O₄

Average Molecular Weight

292.2112

Monoisotopic Molecular Weight

292.067091465

IUPAC Name

2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanimidic acid

Traditional Name

hydroxyflutamide

CAS Registry Number

Not Available

SMILES

CC(C)(O)C(O)=NC1=CC(=C(C=C1)N(=O)=O)C(F)(F)F

InChI Identifier

InChI=1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17)

InChI Key

YPQLFJODEKMJEF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Trifluoromethylbenzenes

Direct Parent

Trifluoromethylbenzenes

Alternative Parents

Substituents

Trifluoromethylbenzene
Nitrobenzene
Anilide
Nitroaromatic compound
N-arylamide
Tertiary alcohol
Carboxamide group
C-nitro compound
Secondary carboxylic acid amide
Organic nitro compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboxylic acid derivative
Organic oxoazanium
Hydrocarbon derivative
Alkyl halide
Organooxygen compound
Organonitrogen compound
Organofluoride
Organic oxygen compound
Organohalogen compound
Organic nitrogen compound
Alkyl fluoride
Organopnictogen compound
Alcohol
Carbonyl group
Organic zwitterion
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

anilide (CHEBI:43064 )

Ontology

Not Available

Kidney (HMDB: HMDB0060949)
Liver (HMDB: HMDB0060949)

Biofluid or Excreta

Non-excretory biofluid

Blood (HMDB: HMDB0060949)

Excreta

Urine (HMDB: HMDB0060949)

Cellular substructure

Cytoplasm (HMDB: HMDB0060949)
Membrane (HMDB: HMDB0060949)

Kidney (HMDB: HMDB0060949)
Liver (HMDB: HMDB0060949)

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	0.0056 g/L	ALOGPS
logP	1.91	ALOGPS
logP	2.94	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	0.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.64 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.88 m³·mol⁻¹	ChemAxon
Polarizability	24.07 Å³	ChemAxon
Number of Rings	1	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]+	162.911	30932474
DeepCCS	[M-H]-	160.553	30932474
DeepCCS	[M-2H]-	194.422	30932474
DeepCCS	[M+Na]+	169.816	30932474
AllCCS	[M+H]+	160.3	32859911
AllCCS	[M+H-H2O]+	157.1	32859911
AllCCS	[M+NH4]+	163.4	32859911
AllCCS	[M+Na]+	164.3	32859911
AllCCS	[M-H]-	158.8	32859911
AllCCS	[M+Na-2H]-	158.5	32859911
AllCCS	[M+HCOO]-	158.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-hydroxyflutamide	CC(C)(O)C(O)=NC1=CC(=C(C=C1)N(=O)=O)C(F)(F)F	2289.0	Standard polar	33892256
2-hydroxyflutamide	CC(C)(O)C(O)=NC1=CC(=C(C=C1)N(=O)=O)C(F)(F)F	1979.8	Standard non polar	33892256
2-hydroxyflutamide	CC(C)(O)C(O)=NC1=CC(=C(C=C1)N(=O)=O)C(F)(F)F	1924.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-hydroxyflutamide,1TMS,isomer #1	CC(C)(O[Si](C)(C)C)C(O)=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1	1812.1	Semi standard non polar	33892256
2-hydroxyflutamide,1TMS,isomer #2	CC(C)(O)C(=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)O[Si](C)(C)C	1740.4	Semi standard non polar	33892256
2-hydroxyflutamide,2TMS,isomer #1	CC(C)(O[Si](C)(C)C)C(=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)O[Si](C)(C)C	1797.9	Semi standard non polar	33892256
2-hydroxyflutamide,1TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C(O)=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1	2073.4	Semi standard non polar	33892256
2-hydroxyflutamide,1TBDMS,isomer #2	CC(C)(O)C(=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)O[Si](C)(C)C(C)(C)C	1994.9	Semi standard non polar	33892256
2-hydroxyflutamide,2TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C(=NC1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)O[Si](C)(C)C(C)(C)C	2289.1	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 - 2-hydroxyflutamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9050000000-f84e588ae9034a41b2dc	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-hydroxyflutamide GC-MS (2 TMS) - 70eV, Positive	splash10-0089-9611200000-62d9053b443fcb365642	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-hydroxyflutamide 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 - 2-hydroxyflutamide 90V, Negative-QTOF	splash10-06g0-9800000000-18021dcb8f1e955f52ad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-hydroxyflutamide 75V, Negative-QTOF	splash10-0a6r-6940000000-dd38c2394309e1626e1e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-hydroxyflutamide 75V, Positive-QTOF	splash10-0a6r-6940000000-81afeee01eada15bcf38	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-hydroxyflutamide 60V, Negative-QTOF	splash10-0a4i-2490000000-6d0e498f9c29ac103dd7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-hydroxyflutamide 15V, Negative-QTOF	splash10-0006-0090000000-1892a491307294bb679e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-hydroxyflutamide 30V, Negative-QTOF	splash10-0a4i-0090000000-73482035831e8bedb25c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-hydroxyflutamide 45V, Negative-QTOF	splash10-0a4i-0090000000-e7bc28de00b2591fa92a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyflutamide 10V, Positive-QTOF	splash10-0006-0090000000-4c17b53efb57846397e4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyflutamide 20V, Positive-QTOF	splash10-00kr-3090000000-d9e96ed3ee61c4eaf8ed	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyflutamide 40V, Positive-QTOF	splash10-059f-9010000000-67e035c44d2e533ec730	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyflutamide 10V, Negative-QTOF	splash10-0006-0090000000-c848958ccc3b75da2ac3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyflutamide 20V, Negative-QTOF	splash10-0006-1190000000-78cf87749f2c226b1da4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyflutamide 40V, Negative-QTOF	splash10-0k9i-9200000000-b8932182dc7010369052	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

C14204

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hydroxyflutamide

METLIN ID

Not Available

PubChem Compound

91649

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 2-hydroxyflutamide (HMDB0060949)

MOL for HMDB0060949 (2-hydroxyflutamide)

3D MOL for HMDB0060949 (2-hydroxyflutamide)

3D SDF for HMDB0060949 (2-hydroxyflutamide)

3D-SDF for HMDB0060949 (2-hydroxyflutamide)

PDB for HMDB0060949 (2-hydroxyflutamide)

3D PDB for HMDB0060949 (2-hydroxyflutamide)

SMILES for HMDB0060949 (2-hydroxyflutamide)

INCHI for HMDB0060949 (2-hydroxyflutamide)

Structure for HMDB0060949 (2-hydroxyflutamide)

3D Structure for HMDB0060949 (2-hydroxyflutamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra