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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014492

Secondary Accession Numbers

HMDB14492

Metabolite Identification

Common Name

Nitisinone

Description

Nitisinone is only found in individuals that have used or taken this drug. It is a synthetic reversible inhibitor of 4-hydroxyphenylpyruvate dioxygenase. It is used in the treatment of hereditary tyrosinemia type 1. It is sold under the brand name Orfadin. [Wikipedia ]Nitisinone is a competitive inhibitor of 4-hydroxyphenyl-pyruvate dioxygenase, an enzyme upstream of fumarylacetoacetate hydrolyase (FAH) in the tyrosine catabolic pathway. By inhibiting the normal catabolism of tyrosine in patients with hereditary tyrosinemia type 1 (HT-1), nitisinone prevents the accumulation of the catabolic intermediates maleylacetoacetate and fumarylacetoacetate.

Structure

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

HMDB0014492
     RDKit          3D
Nitisinone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.8406    2.0490   -0.9275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9942    0.9955   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7134    1.0230    0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220    0.4738    0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0412   -0.4900   -0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532   -1.2070   -0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6493   -2.3530   -0.2839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521   -0.2856   -0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459   -0.9360   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580   -2.1840   -0.0139 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876   -0.3979   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074    0.9606   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244    1.5037    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5176    0.6826    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8541    1.3070    0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0027    2.3031   -0.3751 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826    1.9045    1.8147 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8759    0.3861    0.5841 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -0.6386    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976   -1.1986   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073   -2.6069   -0.5813 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.0121   -3.3541   -0.0991 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -3.1948   -1.4054 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1868    0.3487    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7335    2.0625    1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8240    1.3137    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125   -0.0170    1.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9117   -1.1828   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2174    0.1537   -1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5579   -0.3057   -2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    1.6414   -0.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    2.5592    0.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893   -1.3162    0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  8  2  1  0
 20 11  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 12 31  1  0
 13 32  1  0
 19 33  1  0
M  CHG  2  21   1  23  -1
M  END

348
  Mrv0541 02231214372D          

 23 24  0  0  0  0            999 V2000
    3.7935   -2.8876    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185   -2.0625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685   -2.0625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.3645    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 23  1  0  0  0  0
  3 23  1  0  0  0  0
  4 14  2  0  0  0  0
  5 15  2  0  0  0  0
  6 16  2  0  0  0  0
  7  9  1  0  0  0  0
  8  9  2  0  0  0  0
  9 18  1  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
M  CHG  2   7  -1   9   1
M  END
> <DATABASE_ID>
HMDB0014492

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-][N+](=O)C1=C(C=CC(=C1)C(F)(F)F)C(=O)C1C(=O)CCCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2

> <INCHI_KEY>
OUBCNLGXQFSTLU-UHFFFAOYSA-N

> <FORMULA>
C14H10F3NO5

> <MOLECULAR_WEIGHT>
329.2281

> <EXACT_MASS>
329.05110705

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.736164608656512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
3.1276615006666666

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7114778153469925

> <JCHEM_PKA_STRONGEST_BASIC>
-7.305852447977973

> <JCHEM_POLAR_SURFACE_AREA>
97.03

> <JCHEM_REFRACTIVITY>
72.3478

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nitisinone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014492
     RDKit          3D
Nitisinone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.8406    2.0490   -0.9275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9942    0.9955   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7134    1.0230    0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220    0.4738    0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0412   -0.4900   -0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532   -1.2070   -0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6493   -2.3530   -0.2839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521   -0.2856   -0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459   -0.9360   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580   -2.1840   -0.0139 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876   -0.3979   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074    0.9606   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244    1.5037    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5176    0.6826    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8541    1.3070    0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0027    2.3031   -0.3751 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826    1.9045    1.8147 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8759    0.3861    0.5841 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -0.6386    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976   -1.1986   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073   -2.6069   -0.5813 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.0121   -3.3541   -0.0991 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -3.1948   -1.4054 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1868    0.3487    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7335    2.0625    1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8240    1.3137    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125   -0.0170    1.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9117   -1.1828   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2174    0.1537   -1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5579   -0.3057   -2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    1.6414   -0.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    2.5592    0.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893   -1.3162    0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  8  2  1  0
 20 11  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 12 31  1  0
 13 32  1  0
 19 33  1  0
M  CHG  2  21   1  23  -1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 348                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       7.081  -5.390   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       8.621  -3.850   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       5.541  -3.850   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0       9.748   0.770   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.081   5.390   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.748   3.080   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.080   0.000   0.000  0.00  0.00           O-1
HETATM    8  O   UNK     0       4.414   2.310   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       4.414   0.770   0.000  0.00  0.00           N+1
HETATM   10  C   UNK     0       8.415   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.748  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081  -3.850   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4   14                                                            
CONECT    5   15                                                            
CONECT    6   16                                                            
CONECT    7    9                                                            
CONECT    8    9                                                            
CONECT    9    7    8   18                                                  
CONECT   10   14   15   16                                                  
CONECT   11   12   13                                                       
CONECT   12   11   14                                                       
CONECT   13   11   15                                                       
CONECT   14    4   10   12                                                  
CONECT   15    5   10   13                                                  
CONECT   16    6   10   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18    9   17   21                                                  
CONECT   19   17   22                                                       
CONECT   20   21   22   23                                                  
CONECT   21   18   20                                                       
CONECT   22   19   20                                                       
CONECT   23    1    2    3   20                                             
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0014492
HETATM    1  O1  UNL     1      -1.841   2.049  -0.928  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.994   0.996  -0.368  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.713   1.023   0.958  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.122   0.474   0.750  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.041  -0.490  -0.443  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.753  -1.207  -0.503  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.649  -2.353  -0.284  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.552  -0.286  -0.873  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.346  -0.936  -0.395  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.458  -2.184  -0.014  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.988  -0.398  -0.300  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.207   0.961  -0.050  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.424   1.504   0.219  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.518   0.683   0.252  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.854   1.307   0.562  1.00  0.00           C  
HETATM   16  F1  UNL     1       5.003   2.303  -0.375  1.00  0.00           F  
HETATM   17  F2  UNL     1       4.683   1.904   1.815  1.00  0.00           F  
HETATM   18  F3  UNL     1       5.876   0.386   0.584  1.00  0.00           F  
HETATM   19  C13 UNL     1       3.346  -0.639   0.013  1.00  0.00           C  
HETATM   20  C14 UNL     1       2.098  -1.199  -0.263  1.00  0.00           C  
HETATM   21  N1  UNL     1       2.107  -2.607  -0.581  1.00  0.00           N1+
HETATM   22  O4  UNL     1       3.012  -3.354  -0.099  1.00  0.00           O  
HETATM   23  O5  UNL     1       1.195  -3.195  -1.405  1.00  0.00           O1-
HETATM   24  H1  UNL     1      -2.187   0.349   1.644  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.733   2.063   1.344  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.824   1.314   0.461  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.512  -0.017   1.645  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.912  -1.183  -0.405  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.217   0.154  -1.350  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.558  -0.306  -2.014  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.381   1.641  -0.048  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.533   2.559   0.405  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.189  -1.316   0.046  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7    7    8
CONECT    8    9   30
CONECT    9   10   10   11
CONECT   11   12   12   20
CONECT   12   13   31
CONECT   13   14   14   32
CONECT   14   15   19
CONECT   15   16   17   18
CONECT   19   20   20   33
CONECT   20   21
CONECT   21   22   22   23
END

HMDB0014492
     RDKit          3D
Nitisinone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.8406    2.0490   -0.9275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9942    0.9955   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7134    1.0230    0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220    0.4738    0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0412   -0.4900   -0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532   -1.2070   -0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6493   -2.3530   -0.2839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521   -0.2856   -0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3459   -0.9360   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580   -2.1840   -0.0139 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876   -0.3979   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074    0.9606   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244    1.5037    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5176    0.6826    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8541    1.3070    0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0027    2.3031   -0.3751 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826    1.9045    1.8147 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8759    0.3861    0.5841 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -0.6386    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976   -1.1986   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073   -2.6069   -0.5813 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.0121   -3.3541   -0.0991 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -3.1948   -1.4054 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1868    0.3487    1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7335    2.0625    1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8240    1.3137    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5125   -0.0170    1.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9117   -1.1828   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2174    0.1537   -1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5579   -0.3057   -2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    1.6414   -0.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    2.5592    0.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893   -1.3162    0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  8  2  1  0
 20 11  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 12 31  1  0
 13 32  1  0
 19 33  1  0
M  CHG  2  21   1  23  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(alpha,alpha,alpha-Trifluoro-2-nitro-p-tuluoyl)-1,3-cyclohexanedione	ChEBI
Nitisinona	ChEBI
Nitisinonum	ChEBI
Orfadin	ChEBI
2-(a,a,a-Trifluoro-2-nitro-p-tuluoyl)-1,3-cyclohexanedione	Generator
2-(Α,α,α-trifluoro-2-nitro-p-tuluoyl)-1,3-cyclohexanedione	Generator
NTBC CPD	HMDB
2-(2-Nitro-4-(trifluoromethyl)benzoyl)cyclohexane-1,3-dione	HMDB
2-(2-Nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione	HMDB

Chemical Formula

C₁₄H₁₀F₃NO₅

Average Molecular Weight

329.2281

Monoisotopic Molecular Weight

329.05110705

IUPAC Name

2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione

Traditional Name

nitisinone

CAS Registry Number

104206-65-7

SMILES

[O-][N+](=O)C1=C(C=CC(=C1)C(F)(F)F)C(=O)C1C(=O)CCCC1=O

InChI Identifier

InChI=1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2

InChI Key

OUBCNLGXQFSTLU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoylcyclohexane-1,3-diones. These are alkyl-phenylketones where the alkyl group is a cyclohexane 1,3-dione.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Benzoylcyclohexane-1,3-diones

Alternative Parents

Substituents

Benzoylcyclohexane-1,3-dione
Trifluoromethylbenzene
Nitrobenzene
Benzoyl
Nitroaromatic compound
Aryl alkyl ketone
1,3-diketone
Monocyclic benzene moiety
1,3-dicarbonyl compound
Benzenoid
Organic nitro compound
C-nitro compound
Cyclic ketone
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Organofluoride
Organic oxide
Organohalogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Alkyl halide
Alkyl fluoride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:50378 )
(trifluoromethyl)benzenes (CHEBI:50378 )
cyclohexanones (CHEBI:50378 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014492)

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	0.0081 g/L	Not Available
LogP	1.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0081 g/L	ALOGPS
logP	2.06	ALOGPS
logP	3.13	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	97.03 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.35 m³·mol⁻¹	ChemAxon
Polarizability	26.74 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]+	169.171	30932474
DeepCCS	[M-H]-	166.813	30932474
DeepCCS	[M-2H]-	200.328	30932474
DeepCCS	[M+Na]+	175.536	30932474
AllCCS	[M+H]+	170.5	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	173.6	32859911
AllCCS	[M+Na]+	174.5	32859911
AllCCS	[M-H]-	168.0	32859911
AllCCS	[M+Na-2H]-	167.5	32859911
AllCCS	[M+HCOO]-	167.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nitisinone	[O-][N+](=O)C1=C(C=CC(=C1)C(F)(F)F)C(=O)C1C(=O)CCCC1=O	2283.1	Standard polar	33892256
Nitisinone	[O-][N+](=O)C1=C(C=CC(=C1)C(F)(F)F)C(=O)C1C(=O)CCCC1=O	2107.5	Standard non polar	33892256
Nitisinone	[O-][N+](=O)C1=C(C=CC(=C1)C(F)(F)F)C(=O)C1C(=O)CCCC1=O	2086.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nitisinone,1TMS,isomer #1	C[Si](C)(C)OC1=C(C(=O)C2=CC=C(C(F)(F)F)C=C2[N+](=O)[O-])C(=O)CCC1	2171.5	Semi standard non polar	33892256
Nitisinone,1TMS,isomer #1	C[Si](C)(C)OC1=C(C(=O)C2=CC=C(C(F)(F)F)C=C2[N+](=O)[O-])C(=O)CCC1	2212.5	Standard non polar	33892256
Nitisinone,1TMS,isomer #1	C[Si](C)(C)OC1=C(C(=O)C2=CC=C(C(F)(F)F)C=C2[N+](=O)[O-])C(=O)CCC1	2665.1	Standard polar	33892256
Nitisinone,1TMS,isomer #2	C[Si](C)(C)OC1=CCCC(=O)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2164.9	Semi standard non polar	33892256
Nitisinone,1TMS,isomer #2	C[Si](C)(C)OC1=CCCC(=O)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2231.3	Standard non polar	33892256
Nitisinone,1TMS,isomer #2	C[Si](C)(C)OC1=CCCC(=O)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2681.8	Standard polar	33892256
Nitisinone,2TMS,isomer #1	C[Si](C)(C)OC1=CCCC(O[Si](C)(C)C)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2219.0	Semi standard non polar	33892256
Nitisinone,2TMS,isomer #1	C[Si](C)(C)OC1=CCCC(O[Si](C)(C)C)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2361.8	Standard non polar	33892256
Nitisinone,2TMS,isomer #1	C[Si](C)(C)OC1=CCCC(O[Si](C)(C)C)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2584.9	Standard polar	33892256
Nitisinone,2TMS,isomer #2	C[Si](C)(C)OC1=CCC=C(O[Si](C)(C)C)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2210.7	Semi standard non polar	33892256
Nitisinone,2TMS,isomer #2	C[Si](C)(C)OC1=CCC=C(O[Si](C)(C)C)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2353.5	Standard non polar	33892256
Nitisinone,2TMS,isomer #2	C[Si](C)(C)OC1=CCC=C(O[Si](C)(C)C)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2594.2	Standard polar	33892256
Nitisinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C(=O)C2=CC=C(C(F)(F)F)C=C2[N+](=O)[O-])C(=O)CCC1	2407.8	Semi standard non polar	33892256
Nitisinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C(=O)C2=CC=C(C(F)(F)F)C=C2[N+](=O)[O-])C(=O)CCC1	2421.8	Standard non polar	33892256
Nitisinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C(=O)C2=CC=C(C(F)(F)F)C=C2[N+](=O)[O-])C(=O)CCC1	2718.1	Standard polar	33892256
Nitisinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CCCC(=O)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2391.9	Semi standard non polar	33892256
Nitisinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CCCC(=O)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2421.5	Standard non polar	33892256
Nitisinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CCCC(=O)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2722.8	Standard polar	33892256
Nitisinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCC(O[Si](C)(C)C(C)(C)C)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2692.0	Semi standard non polar	33892256
Nitisinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCC(O[Si](C)(C)C(C)(C)C)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2702.2	Standard non polar	33892256
Nitisinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCC(O[Si](C)(C)C(C)(C)C)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2716.6	Standard polar	33892256
Nitisinone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CCC=C(O[Si](C)(C)C(C)(C)C)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2678.0	Semi standard non polar	33892256
Nitisinone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CCC=C(O[Si](C)(C)C(C)(C)C)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2699.8	Standard non polar	33892256
Nitisinone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CCC=C(O[Si](C)(C)C(C)(C)C)C1C(=O)C1=CC=C(C(F)(F)F)C=C1[N+](=O)[O-]	2718.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nitisinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-9453000000-6678c582428855d7d395	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitisinone 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 - Nitisinone 10V, Positive-QTOF	splash10-001i-0009000000-974033c16a53de383f50	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 20V, Positive-QTOF	splash10-056r-1009000000-0631b4574f9b56f2003c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 40V, Positive-QTOF	splash10-0006-9020000000-bab1729386f1cfe2969f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 10V, Negative-QTOF	splash10-004i-0009000000-c91cd9c3e89ef6ab4236	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 20V, Negative-QTOF	splash10-004i-1009000000-beddd5d5f9f60a53de90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 40V, Negative-QTOF	splash10-000f-9111000000-48ffa1648811e3b1568c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 10V, Positive-QTOF	splash10-0089-0069000000-d1a96c2d31f1c560e24d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 20V, Positive-QTOF	splash10-0229-0193000000-7d678116b1886af26719	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 40V, Positive-QTOF	splash10-01vo-9870000000-f537fa57d0461d07f35b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 10V, Negative-QTOF	splash10-004i-0009000000-587b0e6655b2caea942f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 20V, Negative-QTOF	splash10-004i-0019000000-d789457835a608d224da	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitisinone 40V, Negative-QTOF	splash10-0007-9070000000-25cbb0124c94b26c66b7	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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 DB00348	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00348	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00348

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

103195

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nitisinone

METLIN ID

Not Available

PubChem Compound

115355

PDB ID

Not Available

ChEBI ID

50378

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

Enzymes

Enzyme Details

1. 4-hydroxyphenylpyruvate dioxygenase

General function:: Involved in 4-hydroxyphenylpyruvate dioxygenase activity
Specific function:: Key enzyme in the degradation of tyrosine.
Gene Name:: HPD
Uniprot ID:: P32754
Molecular weight:: 40497.105

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Fisher AA, Davis MW: Alkaptonuric ochronosis with aortic valve and joint replacements and femoral fracture: a case report and literature review. Clin Med Res. 2004 Nov;2(4):209-15. [PubMed:15931360 ]
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Hanauske-Abel HM, Popowicz A, Remotti H, Newfield RS, Levy J: Tyrosinemia I, a model for human diseases mediated by 2-oxoacid-utilizing dioxygenases: hepatotoxin suppression by NTBC does not normalize hepatic collagen metabolism. J Pediatr Gastroenterol Nutr. 2002 Jul;35(1):73-8. [PubMed:12142814 ]
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Santra S, Baumann U: Experience of nitisinone for the pharmacological treatment of hereditary tyrosinaemia type 1. Expert Opin Pharmacother. 2008 May;9(7):1229-36. doi: 10.1517/14656566.9.7.1229. [PubMed:18422479 ]

Showing metabocard for Nitisinone (HMDB0014492)

MOL for HMDB0014492 (Nitisinone)

3D MOL for HMDB0014492 (Nitisinone)

3D SDF for HMDB0014492 (Nitisinone)

3D-SDF for HMDB0014492 (Nitisinone)

PDB for HMDB0014492 (Nitisinone)

3D PDB for HMDB0014492 (Nitisinone)

SMILES for HMDB0014492 (Nitisinone)

INCHI for HMDB0014492 (Nitisinone)

Structure for HMDB0014492 (Nitisinone)

3D Structure for HMDB0014492 (Nitisinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References