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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

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

HMDB0014468

Secondary Accession Numbers

HMDB14468

Metabolite Identification

Common Name

Tolcapone

Description

Tolcapone, also known as tasmar, belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. Tolcapone is a drug which is used as an adjunct to levodopa/carbidopa therapy for the symptomatic treatment of parkinson's disease. this drug is generally reserved for patients with parkinsonian syndrome receiving levodopa/carbidopa who are experiencing symptom fluctuations and are not responding adequately to or are not candidates for other adjunctive therapies. Tolcapone is an extremely weak basic (essentially neutral) compound (based on its pKa). Tolcapone is a potentially toxic compound. Benzophenone substituted on one of the phenyl rings at C-3 and C-4 by hydroxy groups and at C-5 by a nitro group, and on the other phenyl ring by a methyl group at C-4.

Structure

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

HMDB0014468
     RDKit          3D
Tolcapone
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.3726    0.8079   -0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9894    0.3447   -0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218   -0.2893    0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4562   -0.7079    0.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494   -0.5182   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -1.0331    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1660   -2.1910    1.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2621   -0.5414    0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259    0.4637   -0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464    0.9029   -0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2861    1.9378   -1.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8983    0.3391    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2116    0.7797    0.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437   -0.6777    1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5737   -1.2388    1.8150 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.5295   -0.5573    2.1985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4635   -2.5632    2.1603 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2531   -1.1347    1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286    0.1091   -1.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    0.5378   -1.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391    1.4939   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0415   -0.0767   -1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3607    1.2543   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5617   -0.4487    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -1.2056    1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9349    0.9696   -1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908    2.3677   -2.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537    1.5080   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162   -1.9278    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8623    0.2628   -1.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    1.0326   -2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  CHG  2  15   1  17  -1
M  END

323
  Mrv0541 02231214362D          

 20 21  0  0  0  0            999 V2000
    5.6655    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    3.0938    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.8075    3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.6813    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.2365    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2 13  1  0  0  0  0
  3 17  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  2  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 15  2  0  0  0  0
  8 16  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 17  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 14 20  1  0  0  0  0
 15 18  1  0  0  0  0
 16 19  2  0  0  0  0
M  CHG  2   4  -1   6   1
M  END
> <DATABASE_ID>
HMDB0014468

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3

> <INCHI_KEY>
MIQPIUSUKVNLNT-UHFFFAOYSA-N

> <FORMULA>
C14H11NO5

> <MOLECULAR_WEIGHT>
273.2408

> <EXACT_MASS>
273.063722467

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.436268450204295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(4-methylbenzoyl)-3-nitrobenzene-1,2-diol

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.278873788666666

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.630671159623375

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.167245045370144

> <JCHEM_PKA_STRONGEST_BASIC>
-6.417683701145976

> <JCHEM_POLAR_SURFACE_AREA>
103.35

> <JCHEM_REFRACTIVITY>
72.96120000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tolcapone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014468
     RDKit          3D
Tolcapone
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.3726    0.8079   -0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9894    0.3447   -0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218   -0.2893    0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4562   -0.7079    0.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494   -0.5182   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -1.0331    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1660   -2.1910    1.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2621   -0.5414    0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259    0.4637   -0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464    0.9029   -0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2861    1.9378   -1.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8983    0.3391    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2116    0.7797    0.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437   -0.6777    1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5737   -1.2388    1.8150 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.5295   -0.5573    2.1985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4635   -2.5632    2.1603 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2531   -1.1347    1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286    0.1091   -1.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    0.5378   -1.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391    1.4939   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0415   -0.0767   -1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3607    1.2543   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5617   -0.4487    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -1.2056    1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9349    0.9696   -1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908    2.3677   -2.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537    1.5080   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162   -1.9278    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8623    0.2628   -1.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    1.0326   -2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  CHG  2  15   1  17  -1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 323                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      10.576   1.155   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907   0.385   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907   3.465   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.908   5.775   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0       5.241   5.775   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.574   5.005   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0       7.908   1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.242  -1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.242   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.908   2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574   0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574   3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.241   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.242  -4.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908  -1.925   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.576  -1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.241   2.695   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.908  -3.465   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.576  -3.465   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.242  -5.775   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   13                                                            
CONECT    3   17                                                            
CONECT    4    6                                                            
CONECT    5    6                                                            
CONECT    6    4    5   12                                                  
CONECT    7    9   10   11                                                  
CONECT    8    9   15   16                                                  
CONECT    9    1    7    8                                                  
CONECT   10    7   12                                                       
CONECT   11    7   13                                                       
CONECT   12    6   10   17                                                  
CONECT   13    2   11   17                                                  
CONECT   14   18   19   20                                                  
CONECT   15    8   18                                                       
CONECT   16    8   19                                                       
CONECT   17    3   12   13                                                  
CONECT   18   14   15                                                       
CONECT   19   14   16                                                       
CONECT   20   14                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0014468
HETATM    1  C1  UNL     1       5.373   0.808  -0.998  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.989   0.345  -0.657  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.722  -0.289   0.532  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.456  -0.708   0.844  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.349  -0.518  -0.024  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.064  -1.033   0.397  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.166  -2.191   1.032  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.262  -0.541   0.272  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.626   0.464  -0.579  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.946   0.903  -0.646  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.286   1.938  -1.535  1.00  0.00           O  
HETATM   12  C10 UNL     1      -3.898   0.339   0.136  1.00  0.00           C  
HETATM   13  O3  UNL     1      -5.212   0.780   0.066  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.544  -0.678   1.002  1.00  0.00           C  
HETATM   15  N1  UNL     1      -4.574  -1.239   1.815  1.00  0.00           N1+
HETATM   16  O4  UNL     1      -5.530  -0.557   2.199  1.00  0.00           O  
HETATM   17  O5  UNL     1      -4.463  -2.563   2.160  1.00  0.00           O1-
HETATM   18  C12 UNL     1      -2.253  -1.135   1.092  1.00  0.00           C  
HETATM   19  C13 UNL     1       1.629   0.109  -1.200  1.00  0.00           C  
HETATM   20  C14 UNL     1       2.937   0.538  -1.513  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.739   1.494  -0.208  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.042  -0.077  -1.028  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.361   1.254  -1.998  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.562  -0.449   1.218  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.229  -1.206   1.766  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.935   0.970  -1.211  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.591   2.368  -2.126  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.454   1.508  -0.559  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.016  -1.928   1.779  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.862   0.263  -1.951  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.109   1.033  -2.451  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   20
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6   19
CONECT    6    7    7    8
CONECT    8    9    9   18
CONECT    9   10   26
CONECT   10   11   12   12
CONECT   11   27
CONECT   12   13   14
CONECT   13   28
CONECT   14   15   18   18
CONECT   15   16   16   17
CONECT   18   29
CONECT   19   20   20   30
CONECT   20   31
END

HMDB0014468
     RDKit          3D
Tolcapone
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.3726    0.8079   -0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9894    0.3447   -0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218   -0.2893    0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4562   -0.7079    0.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494   -0.5182   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -1.0331    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1660   -2.1910    1.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2621   -0.5414    0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259    0.4637   -0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464    0.9029   -0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2861    1.9378   -1.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8983    0.3391    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2116    0.7797    0.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437   -0.6777    1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5737   -1.2388    1.8150 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.5295   -0.5573    2.1985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4635   -2.5632    2.1603 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.2531   -1.1347    1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286    0.1091   -1.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    0.5378   -1.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391    1.4939   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0415   -0.0767   -1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3607    1.2543   -1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5617   -0.4487    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -1.2056    1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9349    0.9696   -1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908    2.3677   -2.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537    1.5080   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162   -1.9278    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8623    0.2628   -1.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    1.0326   -2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  CHG  2  15   1  17  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-Dihydroxy-4'-methyl-5-nitrobenzophenone	ChEBI
3,4-Dihydroxy-5-nitro-4'-methylbenzophenone	ChEBI
4'-Methyl-3,4-dihydroxy-5-nitrobenzophenone	ChEBI
Tasmar	Kegg
Roche brand OF tolcapone	HMDB
3,4-Dihydroxy-5'-methyl-5-nitrobenzophenone	HMDB
3,4 Dihydroxy 5' methyl 5 nitrobenzophenone	HMDB

Chemical Formula

C₁₄H₁₁NO₅

Average Molecular Weight

273.2408

Monoisotopic Molecular Weight

273.063722467

IUPAC Name

5-(4-methylbenzoyl)-3-nitrobenzene-1,2-diol

Traditional Name

tolcapone

CAS Registry Number

134308-13-7

SMILES

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

InChI Identifier

InChI=1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3

InChI Key

MIQPIUSUKVNLNT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
Diphenylmethane
Aryl-phenylketone
Nitrophenol
Nitrobenzene
Nitroaromatic compound
Benzoyl
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Ketone
Organic nitro compound
C-nitro compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzophenones (CHEBI:63630 )
a small molecule (CPD-7664 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014468)
Membrane (HMDB: HMDB0014468)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

antiparkinson drug (HMDB: HMDB0014468)

EC 2.1.1.6 (catechol O-methyltransferase) inhibitor (HMDB: HMDB0014468)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.057 g/L	Not Available
LogP	4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.057 g/L	ALOGPS
logP	2.63	ALOGPS
logP	3.28	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	5.17	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.96 m³·mol⁻¹	ChemAxon
Polarizability	26.44 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
DarkChem	[M+H]+	165.701	31661259
DarkChem	[M-H]-	168.72	31661259
DeepCCS	[M+H]+	158.744	30932474
DeepCCS	[M-H]-	156.353	30932474
DeepCCS	[M-2H]-	190.089	30932474
DeepCCS	[M+Na]+	166.254	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	156.6	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	158.9	32859911
AllCCS	[M+Na-2H]-	158.2	32859911
AllCCS	[M+HCOO]-	157.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tolcapone	CC1=CC=C(C=C1)C(=O)C1=CC(=C(O)C(O)=C1)[N+]([O-])=O	3616.7	Standard polar	33892256
Tolcapone	CC1=CC=C(C=C1)C(=O)C1=CC(=C(O)C(O)=C1)[N+]([O-])=O	2248.8	Standard non polar	33892256
Tolcapone	CC1=CC=C(C=C1)C(=O)C1=CC(=C(O)C(O)=C1)[N+]([O-])=O	2517.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tolcapone,1TMS,isomer #1	CC1=CC=C(C(=O)C2=CC(O)=C(O[Si](C)(C)C)C([N+](=O)[O-])=C2)C=C1	2527.6	Semi standard non polar	33892256
Tolcapone,1TMS,isomer #2	CC1=CC=C(C(=O)C2=CC(O[Si](C)(C)C)=C(O)C([N+](=O)[O-])=C2)C=C1	2551.1	Semi standard non polar	33892256
Tolcapone,2TMS,isomer #1	CC1=CC=C(C(=O)C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C([N+](=O)[O-])=C2)C=C1	2571.0	Semi standard non polar	33892256
Tolcapone,1TBDMS,isomer #1	CC1=CC=C(C(=O)C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C2)C=C1	2809.6	Semi standard non polar	33892256
Tolcapone,1TBDMS,isomer #2	CC1=CC=C(C(=O)C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C([N+](=O)[O-])=C2)C=C1	2829.5	Semi standard non polar	33892256
Tolcapone,2TBDMS,isomer #1	CC1=CC=C(C(=O)C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C2)C=C1	3072.6	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 - Tolcapone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0q29-3970000000-6534afd6ea55a8b8f923	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolcapone GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-9748400000-548249e165d1b7970004	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolcapone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolcapone 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 - Tolcapone LC-ESI-qTof , Positive-QTOF	splash10-00e9-0980000000-495401c19ad2c2091c1a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolcapone , positive-QTOF	splash10-00e9-0980000000-495401c19ad2c2091c1a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolcapone 60V, Positive-QTOF	splash10-001i-0940000000-7e03275a1aab614db33e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolcapone 90V, Negative-QTOF	splash10-0159-0900000000-58b8b095bc956f663320	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolcapone 75V, Negative-QTOF	splash10-00lr-0910000000-97d2e08975916b96961d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolcapone 90V, Positive-QTOF	splash10-0159-0900000000-64283697ac79a1be77ba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolcapone 60V, Negative-QTOF	splash10-001i-0940000000-d7c768583cd479e96f71	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolcapone 45V, Negative-QTOF	splash10-05c6-0390000000-f450d9a92858b3403548	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolcapone 15V, Negative-QTOF	splash10-00di-0090000000-d84e09a33f805ed7a700	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolcapone 75V, Positive-QTOF	splash10-00lr-0910000000-20fd9f346adeaefc6495	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolcapone 30V, Negative-QTOF	splash10-00di-0090000000-2f9b35f27dfa158fbe47	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 10V, Positive-QTOF	splash10-00di-0090000000-88737fd9fe3cbdd7038b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 20V, Positive-QTOF	splash10-00di-0090000000-4b7de2c2d046ee8b3b1e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 40V, Positive-QTOF	splash10-0hb9-1970000000-b9055dada9fa16c1703e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 10V, Negative-QTOF	splash10-00di-0090000000-7963016dae7c1913c615	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 20V, Negative-QTOF	splash10-00di-0090000000-17f517c8392230298043	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 40V, Negative-QTOF	splash10-00di-5190000000-9b0a168ebf7e529ad1f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 10V, Positive-QTOF	splash10-00di-0390000000-be3569c1ee47e9ff087f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 20V, Positive-QTOF	splash10-00xr-4890000000-d2acd7d77e0195bb275b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 40V, Positive-QTOF	splash10-00mo-9510000000-81222ad94f6a6eb45319	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 10V, Negative-QTOF	splash10-00di-0090000000-41d62228dd7475035015	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 20V, Negative-QTOF	splash10-00di-0090000000-02a4ae01ccd77f2e84e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolcapone 40V, Negative-QTOF	splash10-0007-8900000000-4c7370b8810f64b3021d	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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 DB00323	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00323	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

DB00323

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3848682

KEGG Compound ID

C07949

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tolcapone

METLIN ID

Not Available

PubChem Compound

4659569

PDB ID

TCW

ChEBI ID

63630

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

Guay DR: Tolcapone, a selective catechol-O-methyltransferase inhibitor for treatment of Parkinson's disease. Pharmacotherapy. 1999 Jan;19(1):6-20. [PubMed:9917075 ]
Keating GM, Lyseng-Williamson KA: Tolcapone: a review of its use in the management of Parkinson's disease. CNS Drugs. 2005;19(2):165-84. [PubMed:15697329 ]
Truong DD: Tolcapone: review of its pharmacology and use as adjunctive therapy in patients with Parkinson's disease. Clin Interv Aging. 2009;4:109-13. Epub 2009 May 14. [PubMed:19503773 ]
Forsberg M, Lehtonen M, Heikkinen M, Savolainen J, Jarvinen T, Mannisto PT: Pharmacokinetics and pharmacodynamics of entacapone and tolcapone after acute and repeated administration: a comparative study in the rat. J Pharmacol Exp Ther. 2003 Feb;304(2):498-506. [PubMed:12538800 ]
Kaakkola S: Clinical pharmacology, therapeutic use and potential of COMT inhibitors in Parkinson's disease. Drugs. 2000 Jun;59(6):1233-50. [PubMed:10882160 ]

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Ries V, Selzer R, Eichhorn T, Oertel WH, Eggert K: Replacing a dopamine agonist by the COMT-inhibitor tolcapone as an adjunct to L-dopa in the treatment of Parkinson's disease: a randomized, multicenter, open-label, parallel-group study. Clin Neuropharmacol. 2010 May;33(3):142-50. doi: 10.1097/WNF.0b013e3181d99d6f. [PubMed:20502133 ]
Guay DR: Tolcapone, a selective catechol-O-methyltransferase inhibitor for treatment of Parkinson's disease. Pharmacotherapy. 1999 Jan;19(1):6-20. [PubMed:9917075 ]
Keating GM, Lyseng-Williamson KA: Tolcapone: a review of its use in the management of Parkinson's disease. CNS Drugs. 2005;19(2):165-84. [PubMed:15697329 ]
Truong DD: Tolcapone: review of its pharmacology and use as adjunctive therapy in patients with Parkinson's disease. Clin Interv Aging. 2009;4:109-13. Epub 2009 May 14. [PubMed:19503773 ]
Apud JA, Mattay V, Chen J, Kolachana BS, Callicott JH, Rasetti R, Alce G, Iudicello JE, Akbar N, Egan MF, Goldberg TE, Weinberger DR: Tolcapone improves cognition and cortical information processing in normal human subjects. Neuropsychopharmacology. 2007 May;32(5):1011-20. Epub 2006 Oct 25. [PubMed:17063156 ]
Stocchi F, De Pandis MF: Utility of tolcapone in fluctuating Parkinson's disease. Clin Interv Aging. 2006;1(4):317-25. [PubMed:18046910 ]
Forsberg M, Lehtonen M, Heikkinen M, Savolainen J, Jarvinen T, Mannisto PT: Pharmacokinetics and pharmacodynamics of entacapone and tolcapone after acute and repeated administration: a comparative study in the rat. J Pharmacol Exp Ther. 2003 Feb;304(2):498-506. [PubMed:12538800 ]
Tai CH, Wu RM: Catechol-O-methyltransferase and Parkinson's disease. Acta Med Okayama. 2002 Feb;56(1):1-6. [PubMed:11873938 ]
Kaakkola S: Clinical pharmacology, therapeutic use and potential of COMT inhibitors in Parkinson's disease. Drugs. 2000 Jun;59(6):1233-50. [PubMed:10882160 ]
Ruottinen HM, Rinne UK: COMT inhibition in the treatment of Parkinson's disease. J Neurol. 1998 Nov;245(11 Suppl 3):P25-34. [PubMed:9808337 ]

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 ]

Showing metabocard for Tolcapone (HMDB0014468)

MOL for HMDB0014468 (Tolcapone)

3D MOL for HMDB0014468 (Tolcapone)

3D SDF for HMDB0014468 (Tolcapone)

3D-SDF for HMDB0014468 (Tolcapone)

PDB for HMDB0014468 (Tolcapone)

3D PDB for HMDB0014468 (Tolcapone)

SMILES for HMDB0014468 (Tolcapone)

INCHI for HMDB0014468 (Tolcapone)

Structure for HMDB0014468 (Tolcapone)

3D Structure for HMDB0014468 (Tolcapone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References