Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

enzymes (3) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:21:20 UTC

Update Date

2022-03-07 02:51:22 UTC

HMDB ID

HMDB0012226

Secondary Accession Numbers

HMDB12226

Metabolite Identification

Common Name

Entacapone

Description

Entacapone, also known as comtan or comtess, belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Entacapone is a drug which is used as an adjunct to levodopa / carbidopa in the symptomatic treatment of patients with idiopathic parkinson's disease who experience the signs and symptoms of end-of-dose "wearing-off". Based on a literature review a significant number of articles have been published on Entacapone.

Structure

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

HMDB0012226
     RDKit          3D
Entacapone
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.7942    1.6683   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017    0.4201    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575    0.0566   -0.0694 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9271   -0.7669   -1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372   -2.2223   -0.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8139    0.5450    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9732    1.3604    1.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534    0.2327    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0411   -0.7201   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2986   -1.5006   -1.5660 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    0.7885    0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415    0.4927    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8151    0.1875    1.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1441   -0.0773    1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0551   -0.3873    2.4427 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5968   -0.0325    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9424   -0.3010   -0.1217 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    0.2673   -0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2943    0.2929   -2.2403 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.5170    0.0433   -3.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6155    0.5786   -2.4807 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.4180    0.5302   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9906    2.0980   -0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6734    1.4577   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1099    2.3680    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1923    0.5159    1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9787   -0.4483    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514   -0.5044   -1.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9415   -0.6355   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1844   -2.7889   -1.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5601   -2.2874    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8504   -2.7083   -0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874    1.4737    1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4576    0.1526    2.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807   -0.4083    3.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5829   -0.5221    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    0.7812   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  3  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  2  0
 22 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
 11 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 22 37  1  0
M  CHG  2  19   1  21  -1
M  END

494
  Mrv0541 02231214432D          

 22 22  0  0  0  0            999 V2000
    3.7935    1.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7284    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.9842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1409    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.0784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4  7  1  0  0  0  0
  5  7  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 19  1  0  0  0  0
  8 22  3  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  2  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
 15 22  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  CHG  2   4  -1   7   1
M  END
> <DATABASE_ID>
HMDB0012226

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N

> <INCHI_IDENTIFIER>
InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+

> <INCHI_KEY>
JRURYQJSLYLRLN-BJMVGYQFSA-N

> <FORMULA>
C14H15N3O5

> <MOLECULAR_WEIGHT>
305.286

> <EXACT_MASS>
305.101170605

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.482544434027368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
1.634823854666667

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.717541933482945

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.683746978745036

> <JCHEM_PKA_STRONGEST_BASIC>
-0.035749310639829

> <JCHEM_POLAR_SURFACE_AREA>
130.37999999999997

> <JCHEM_REFRACTIVITY>
80.51279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
entacapone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012226
     RDKit          3D
Entacapone
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.7942    1.6683   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017    0.4201    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575    0.0566   -0.0694 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9271   -0.7669   -1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372   -2.2223   -0.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8139    0.5450    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9732    1.3604    1.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534    0.2327    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0411   -0.7201   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2986   -1.5006   -1.5660 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    0.7885    0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415    0.4927    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8151    0.1875    1.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1441   -0.0773    1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0551   -0.3873    2.4427 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5968   -0.0325    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9424   -0.3010   -0.1217 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    0.2673   -0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2943    0.2929   -2.2403 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.5170    0.0433   -3.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6155    0.5786   -2.4807 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.4180    0.5302   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9906    2.0980   -0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6734    1.4577   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1099    2.3680    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1923    0.5159    1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9787   -0.4483    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514   -0.5044   -1.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9415   -0.6355   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1844   -2.7889   -1.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5601   -2.2874    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8504   -2.7083   -0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874    1.4737    1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4576    0.1526    2.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807   -0.4083    3.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5829   -0.5221    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    0.7812   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  3  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  2  0
 22 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
 11 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 22 37  1  0
M  CHG  2  19   1  21  -1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 494                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.081   3.704   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.748  -3.996   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081  -5.536   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080  -3.226   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0       4.414  -5.536   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       9.748   3.704   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.414  -3.996   0.000  0.00  0.00           N+1
HETATM    8  N   UNK     0      11.082  -0.146   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.748   5.244   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.082   2.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   2.934   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   6.014   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.416   3.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -0.916   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   1.394   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   0.624   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -1.686   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -1.686   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748  -3.226   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -3.226   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.081  -3.996   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.748   0.624   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4    7                                                            
CONECT    5    7                                                            
CONECT    6    9   10   11                                                  
CONECT    7    4    5   19                                                  
CONECT    8   22                                                            
CONECT    9    6   12                                                       
CONECT   10    6   13                                                       
CONECT   11    1    6   15                                                  
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   16   17   18                                                  
CONECT   15   11   16   22                                                  
CONECT   16   14   15                                                       
CONECT   17   14   19                                                       
CONECT   18   14   20                                                       
CONECT   19    7   17   21                                                  
CONECT   20    2   18   21                                                  
CONECT   21    3   19   20                                                  
CONECT   22    8   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0012226
HETATM    1  C1  UNL     1      -4.794   1.668  -0.225  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.302   0.420   0.428  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.958   0.057  -0.069  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.927  -0.767  -1.243  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.837  -2.222  -0.852  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.814   0.545   0.578  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.973   1.360   1.575  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.453   0.233   0.251  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.041  -0.720  -0.773  1.00  0.00           C  
HETATM   10  N2  UNL     1       0.299  -1.501  -1.566  1.00  0.00           N  
HETATM   11  C8  UNL     1       0.556   0.788   0.945  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.941   0.493   0.633  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.815   0.188   1.672  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.144  -0.077   1.433  1.00  0.00           C  
HETATM   15  O2  UNL     1       5.055  -0.387   2.443  1.00  0.00           O  
HETATM   16  C12 UNL     1       4.597  -0.032   0.118  1.00  0.00           C  
HETATM   17  O3  UNL     1       5.942  -0.301  -0.122  1.00  0.00           O  
HETATM   18  C13 UNL     1       3.752   0.267  -0.927  1.00  0.00           C  
HETATM   19  N3  UNL     1       4.294   0.293  -2.240  1.00  0.00           N1+
HETATM   20  O4  UNL     1       3.517   0.043  -3.185  1.00  0.00           O  
HETATM   21  O5  UNL     1       5.616   0.579  -2.481  1.00  0.00           O1-
HETATM   22  C14 UNL     1       2.418   0.530  -0.657  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.991   2.098  -0.852  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.673   1.458  -0.867  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.110   2.368   0.589  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.192   0.516   1.535  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.979  -0.448   0.265  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.151  -0.504  -1.976  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.942  -0.636  -1.773  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.184  -2.789  -1.523  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.560  -2.287   0.223  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.850  -2.708  -0.925  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.287   1.474   1.755  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.458   0.153   2.708  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.681  -0.408   3.382  1.00  0.00           H  
HETATM   36  H14 UNL     1       6.583  -0.522   0.610  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.777   0.781  -1.513  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4    6
CONECT    4    5   28   29
CONECT    5   30   31   32
CONECT    6    7    7    8
CONECT    8    9   11   11
CONECT    9   10   10   10
CONECT   11   12   33
CONECT   12   13   13   22
CONECT   13   14   34
CONECT   14   15   16   16
CONECT   15   35
CONECT   16   17   18
CONECT   17   36
CONECT   18   19   22   22
CONECT   19   20   20   21
CONECT   22   37
END

HMDB0012226
     RDKit          3D
Entacapone
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.7942    1.6683   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017    0.4201    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575    0.0566   -0.0694 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9271   -0.7669   -1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372   -2.2223   -0.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8139    0.5450    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9732    1.3604    1.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534    0.2327    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0411   -0.7201   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2986   -1.5006   -1.5660 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    0.7885    0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415    0.4927    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8151    0.1875    1.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1441   -0.0773    1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0551   -0.3873    2.4427 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5968   -0.0325    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9424   -0.3010   -0.1217 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7520    0.2673   -0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2943    0.2929   -2.2403 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.5170    0.0433   -3.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6155    0.5786   -2.4807 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.4180    0.5302   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9906    2.0980   -0.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6734    1.4577   -0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1099    2.3680    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1923    0.5159    1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9787   -0.4483    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514   -0.5044   -1.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9415   -0.6355   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1844   -2.7889   -1.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5601   -2.2874    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8504   -2.7083   -0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874    1.4737    1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4576    0.1526    2.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807   -0.4083    3.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5829   -0.5221    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    0.7812   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  3  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  2  0
 22 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
 11 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 22 37  1  0
M  CHG  2  19   1  21  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-alpha-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide	ChEBI
Comtan	ChEBI
Comtess	ChEBI
Entacapona	ChEBI
Entacaponum	ChEBI
N,N-Diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide	ChEBI
(e)-a-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide	Generator
(e)-Α-cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide	Generator
2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide	HMDB
Orion brand OF entacapone	HMDB
Novartis brand OF entacapone	HMDB

Chemical Formula

C₁₄H₁₅N₃O₅

Average Molecular Weight

305.286

Monoisotopic Molecular Weight

305.101170605

IUPAC Name

(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide

Traditional Name

entacapone

CAS Registry Number

130929-57-6

SMILES

CCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N

InChI Identifier

InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+

InChI Key

JRURYQJSLYLRLN-BJMVGYQFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Hydroxycinnamic acid or derivatives
Nitrophenol
Nitrobenzene
Nitroaromatic compound
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
C-nitro compound
Organic nitro compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Carbonitrile
Nitrile
Organic oxoazanium
Organic 1,3-dipolar compound
Organic nitrogen compound
Organic zwitterion
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:4798 )
catechols (CHEBI:4798 )
nitrile (CHEBI:4798 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0012226)
extracellular (HMDB: HMDB0012226)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

antiparkinson drug (HMDB: HMDB0012226)
central nervous system drug (HMDB: HMDB0012226)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antidyskinesia agent (HMDB: HMDB0012226)

EC 2.1.1.6 (catechol O-methyltransferase) inhibitor (HMDB: HMDB0012226)

Physical Properties

State

Solid

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	0.08 g/L	ALOGPS
logP	2.5	ALOGPS
logP	1.63	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	5.68	ChemAxon
pKa (Strongest Basic)	-0.036	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	130.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.51 m³·mol⁻¹	ChemAxon
Polarizability	29.48 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]+	165.243	30932474
DeepCCS	[M-H]-	161.416	30932474
DeepCCS	[M-2H]-	197.764	30932474
DeepCCS	[M+Na]+	173.809	30932474
AllCCS	[M+H]+	168.7	32859911
AllCCS	[M+H-H2O]+	165.5	32859911
AllCCS	[M+NH4]+	171.7	32859911
AllCCS	[M+Na]+	172.6	32859911
AllCCS	[M-H]-	169.2	32859911
AllCCS	[M+Na-2H]-	169.1	32859911
AllCCS	[M+HCOO]-	169.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Entacapone	CCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N	3690.9	Standard polar	33892256
Entacapone	CCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N	2334.1	Standard non polar	33892256
Entacapone	CCN(CC)C(=O)C(=C\C1=CC(=C(O)C(O)=C1)[N+]([O-])=O)\C#N	2629.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Entacapone,1TMS,isomer #1	CCN(CC)C(=O)/C(C#N)=C/C1=CC(O)=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1	2708.9	Semi standard non polar	33892256
Entacapone,1TMS,isomer #2	CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C)=C(O)C([N+](=O)[O-])=C1	2731.5	Semi standard non polar	33892256
Entacapone,2TMS,isomer #1	CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1	2752.1	Semi standard non polar	33892256
Entacapone,1TBDMS,isomer #1	CCN(CC)C(=O)/C(C#N)=C/C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1	2947.4	Semi standard non polar	33892256
Entacapone,1TBDMS,isomer #2	CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C([N+](=O)[O-])=C1	2966.0	Semi standard non polar	33892256
Entacapone,2TBDMS,isomer #1	CCN(CC)C(=O)/C(C#N)=C/C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1	3157.2	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 - Entacapone GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-4190000000-da6b28638ec4920bd58a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Entacapone GC-MS (2 TMS) - 70eV, Positive	splash10-0059-6004900000-14645ab585cbbed0ca38	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Entacapone 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 - Entacapone LC-ESI-qTof , Positive-QTOF	splash10-0a4i-0329000000-8d20a5650e9c1b1c8275	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Entacapone , positive-QTOF	splash10-0a4i-0329000000-8d20a5650e9c1b1c8275	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 10V, Positive-QTOF	splash10-0a4i-0009000000-6e08b463d5af43617517	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 20V, Positive-QTOF	splash10-0udr-1069000000-5075a6f93c2b72c3483a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 40V, Positive-QTOF	splash10-0fkc-9240000000-27e088a40b83e29661e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 10V, Negative-QTOF	splash10-0udi-0009000000-29c32f9a04e379fce5fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 20V, Negative-QTOF	splash10-0udi-2009000000-6d53b89d8a9ecd3b180e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 40V, Negative-QTOF	splash10-00dl-9100000000-5f330d3ad8cb0af17a9a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 10V, Positive-QTOF	splash10-0a4i-0009000000-62e9f24f62db1840e2e0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 20V, Positive-QTOF	splash10-001i-1292000000-28b9a09056bdc465cd19	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 40V, Positive-QTOF	splash10-0a4i-1590000000-58fe447bc05aa8420188	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 10V, Negative-QTOF	splash10-0udi-0039000000-85f49c3b07fd9b1dd7bd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 20V, Negative-QTOF	splash10-0pb9-1693000000-bf7093c3dc0b31a75e5d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Entacapone 40V, Negative-QTOF	splash10-0a4j-5910000000-658aee735015de149a67	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

DB00494

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028870

KNApSAcK ID

Not Available

Chemspider ID

4444537

KEGG Compound ID

C07943

BioCyc ID

CPD-7662

BiGG ID

Not Available

Wikipedia Link

Entacapone

METLIN ID

Not Available

PubChem Compound

5281081

PDB ID

Not Available

ChEBI ID

4798

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

Valkovic P, Benetin J, Blazicek P, Valkovicova L, Gmitterova K, Kukumberg P: Reduced plasma homocysteine levels in levodopa/entacapone treated Parkinson patients. Parkinsonism Relat Disord. 2005 Jun;11(4):253-6. Epub 2005 Apr 20. [PubMed:15878587 ]
Durif F, Devaux I, Pere JJ, Delumeau JC, Bourdeix I: Efficacy and tolerability of entacapone as adjunctive therapy to levodopa in patients with Parkinson's disease and end-of-dose deterioration in daily medical practice: an open, multicenter study. Eur Neurol. 2001;45(2):111-8. [PubMed:11244274 ]
Factor SA, Molho ES, Feustel PJ, Brown DL, Evans SM: Long-term comparative experience with tolcapone and entacapone in advanced Parkinson's disease. Clin Neuropharmacol. 2001 Sep-Oct;24(5):295-9. [PubMed:11586115 ]
Leppanen J, Savolainen J, Nevalainen T, Forsberg M, Huuskonen J, Taipale H, Gynther J, Mannisto PT, Jarvinen T: Synthesis and in-vitro/in-vivo evaluation of orally administered entacapone prodrugs. J Pharm Pharmacol. 2001 Nov;53(11):1489-98. [PubMed:11732751 ]
Authors unspecified: Entacapone/levodopa/carbidopa combination tablet: Stalevo. Drugs R D. 2003;4(5):310-1. [PubMed:12952501 ]
Authors unspecified: Levodopa + carbidopa + entacapone. Entacapone: a second look: new preparations. Parkinson's disease: a modest effect. Prescrire Int. 2005 Apr;14(76):51-4. [PubMed:15875340 ]
Gottwald MD: Entacapone, a catechol-O-methyltransferase inhibitor for treating Parkinson's disease: review and current status. Expert Opin Investig Drugs. 1999 Apr;8(4):453-62. [PubMed:15992091 ]
Kinnings SL, Liu N, Buchmeier N, Tonge PJ, Xie L, Bourne PE: Drug discovery using chemical systems biology: repositioning the safe medicine Comtan to treat multi-drug and extensively drug resistant tuberculosis. PLoS Comput Biol. 2009 Jul;5(7):e1000423. doi: 10.1371/journal.pcbi.1000423. Epub 2009 Jul 3. [PubMed:19578428 ]
Hamaue N, Ogata A, Terado M, Tsuchida S, Yabe I, Sasaki H, Hirafuji M, Togashi H, Aoki T: Entacapone, a catechol-O-methyltransferase inhibitor, improves the motor activity and dopamine content of basal ganglia in a rat model of Parkinson's disease induced by Japanese encephalitis virus. Brain Res. 2010 Jan 14;1309:110-5. doi: 10.1016/j.brainres.2009.10.055. Epub 2009 Oct 29. [PubMed:19879254 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Enzyme Details

2. 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

Enzyme Details

3. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Showing metabocard for Entacapone (HMDB0012226)

MOL for HMDB0012226 (Entacapone)

3D MOL for HMDB0012226 (Entacapone)

3D SDF for HMDB0012226 (Entacapone)

3D-SDF for HMDB0012226 (Entacapone)

PDB for HMDB0012226 (Entacapone)

3D PDB for HMDB0012226 (Entacapone)

SMILES for HMDB0012226 (Entacapone)

INCHI for HMDB0012226 (Entacapone)

Structure for HMDB0012226 (Entacapone)

3D Structure for HMDB0012226 (Entacapone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes