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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (1) Show 3 proteins XML

enzymes (2)transporters (1) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014959

Secondary Accession Numbers

HMDB14959

Metabolite Identification

Common Name

Carprofen

Description

Carprofen is a non-steroidal anti-inflammatory drug (NSAID) that is used by veterinarians as a supportive treatment for the relief of arthritic symptoms in geriatric dogs. Carprofen was previously used in human medicine for over 10 years (1985-1995). It was generally well tolerated, with the majority of adverse effects being mild, such as gastro-intestinal pain and nausea, similar to those recorded with aspirin and other non-steroidal anti-inflammatory drugs. It is no longer marketed for human usage, after being withdrawn on commercial grounds. [Wikipedia ]

Structure

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

HMDB0014959
     RDKit          3D
Carprofen
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.5526    0.2244   -1.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2288   -0.4015   -0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496    0.4282    0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4865    1.4922    0.1988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7605    0.0746    1.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7767   -0.4813   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1553   -1.7024   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009   -1.8138    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9393   -0.6384    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3451    0.5955   -0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    0.6614   -0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280    1.5006    0.0986 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5047    0.8919    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7842    1.3653    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265    0.4705    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6304   -0.9007    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9937   -1.9623    0.9846 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3467   -1.3646    0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986   -0.4725    0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5529    0.7141   -1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    0.9235   -2.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7004   -0.5775   -2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6593   -1.4308   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2708    0.5234    2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7930   -2.5853   -0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852   -2.7873    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487    1.6578   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789    2.5293    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9724    2.4503    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217    0.8244    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1646   -2.4355    0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  6  1  0
 19 13  1  0
 19  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END

821
  Mrv0541 02231215022D          

 19 21  0  0  1  0            999 V2000
    1.5842   -1.3784    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9413   -0.2544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9253   -1.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8588    0.8874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2548   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4997    0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4628   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607   -0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180    0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6348    0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3039    0.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7974   -0.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6057   -0.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9203   -0.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4137    0.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8767    0.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1119   -0.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1672   -0.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8570   -0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2 18  1  0  0  0  0
  3 18  2  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5 12  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  2  0  0  0  0
  7 14  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  2  0  0  0  0
  8 13  1  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
 10 18  1  0  0  0  0
 12 13  2  0  0  0  0
 14 17  2  0  0  0  0
 15 19  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014959

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)=O)C1=CC2=C(C=C1)C1=C(N2)C=CC(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12ClNO2/c1-8(15(18)19)9-2-4-11-12-7-10(16)3-5-13(12)17-14(11)6-9/h2-8,17H,1H3,(H,18,19)

> <INCHI_KEY>
PUXBGTOOZJQSKH-UHFFFAOYSA-N

> <FORMULA>
C15H12ClNO2

> <MOLECULAR_WEIGHT>
273.714

> <EXACT_MASS>
273.05565634

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.558252351664283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(6-chloro-9H-carbazol-2-yl)propanoic acid

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
3.8756649333333324

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.80425798051407

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.415797667111492

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
74.15910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carprofen

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014959
     RDKit          3D
Carprofen
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.5526    0.2244   -1.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2288   -0.4015   -0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496    0.4282    0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4865    1.4922    0.1988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7605    0.0746    1.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7767   -0.4813   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1553   -1.7024   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009   -1.8138    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9393   -0.6384    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3451    0.5955   -0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    0.6614   -0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280    1.5006    0.0986 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5047    0.8919    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7842    1.3653    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265    0.4705    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6304   -0.9007    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9937   -1.9623    0.9846 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3467   -1.3646    0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986   -0.4725    0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5529    0.7141   -1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    0.9235   -2.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7004   -0.5775   -2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6593   -1.4308   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2708    0.5234    2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7930   -2.5853   -0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852   -2.7873    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487    1.6578   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789    2.5293    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9724    2.4503    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217    0.8244    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1646   -2.4355    0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  6  1  0
 19 13  1  0
 19  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 821                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       2.957  -2.573   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0      14.824  -0.475   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.927  -2.196   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.203   1.656   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.942  -0.619   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.399   0.787   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.464  -0.619   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.940  -0.006   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.007   0.787   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.385   0.307   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.901   1.131   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.955  -1.779   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.464  -1.471   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.451  -1.779   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.506   1.131   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.837   1.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.942  -1.471   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.379  -0.788   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.466  -0.006   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   18                                                            
CONECT    4    6    9                                                       
CONECT    5    6    7   12                                                  
CONECT    6    4    5   11                                                  
CONECT    7    5    9   14                                                  
CONECT    8   10   11   13                                                  
CONECT    9    4    7   15                                                  
CONECT   10    8   16   18                                                  
CONECT   11    6    8                                                       
CONECT   12    5   13                                                       
CONECT   13    8   12                                                       
CONECT   14    7   17                                                       
CONECT   15    9   19                                                       
CONECT   16   10                                                            
CONECT   17    1   14   19                                                  
CONECT   18    2    3   10                                                  
CONECT   19   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0014959
HETATM    1  C1  UNL     1      -3.553   0.224  -1.931  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.229  -0.401  -0.584  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.850   0.428   0.468  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.486   1.492   0.199  1.00  0.00           O  
HETATM    5  O2  UNL     1      -3.761   0.075   1.801  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.777  -0.481  -0.343  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.155  -1.702  -0.198  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.201  -1.814   0.028  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.939  -0.638   0.109  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.345   0.595  -0.031  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.015   0.661  -0.257  1.00  0.00           C  
HETATM   12  N1  UNL     1       1.328   1.501   0.099  1.00  0.00           N  
HETATM   13  C10 UNL     1       2.505   0.892   0.313  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.784   1.365   0.507  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.826   0.470   0.709  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.630  -0.901   0.724  1.00  0.00           C  
HETATM   17 CL1  UNL     1       5.994  -1.962   0.985  1.00  0.00          CL  
HETATM   18  C14 UNL     1       3.347  -1.365   0.529  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.299  -0.473   0.326  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.553   0.714  -1.818  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.770   0.923  -2.272  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.700  -0.577  -2.710  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.659  -1.431  -0.619  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.271   0.523   2.528  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.793  -2.585  -0.272  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.685  -2.787   0.142  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.449   1.658  -0.363  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.179   2.529   0.038  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.972   2.450   0.500  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.822   0.824   0.860  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.165  -2.436   0.536  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    6   23
CONECT    3    4    4    5
CONECT    5   24
CONECT    6    7    7   11
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   10   19
CONECT   10   11   11   12
CONECT   11   27
CONECT   12   13   28
CONECT   13   14   14   19
CONECT   14   15   29
CONECT   15   16   16   30
CONECT   16   17   18
CONECT   18   19   19   31
END

HMDB0014959
     RDKit          3D
Carprofen
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.5526    0.2244   -1.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2288   -0.4015   -0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496    0.4282    0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4865    1.4922    0.1988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7605    0.0746    1.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7767   -0.4813   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1553   -1.7024   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009   -1.8138    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9393   -0.6384    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3451    0.5955   -0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    0.6614   -0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280    1.5006    0.0986 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5047    0.8919    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7842    1.3653    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265    0.4705    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6304   -0.9007    0.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9937   -1.9623    0.9846 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3467   -1.3646    0.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986   -0.4725    0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5529    0.7141   -1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    0.9235   -2.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7004   -0.5775   -2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6593   -1.4308   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2708    0.5234    2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7930   -2.5853   -0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852   -2.7873    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487    1.6578   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789    2.5293    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9724    2.4503    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217    0.8244    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1646   -2.4355    0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  6  1  0
 19 13  1  0
 19  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-6-Chloro-alpha-methylcarbazole-2-acetic acid	ChEBI
(+/-)-2-(3-chloro-9H-carbazol-7-yl)propanoic acid	ChEBI
2-(6-Chloro-9H-carbazol-2-yl)-propionic acid	ChEBI
6-Chloro-alpha-methyl-9H-carbazole-2-acetic acid	ChEBI
Carprofene	ChEBI
Carprofeno	ChEBI
Carprofenum	ChEBI
Rimadyl	Kegg
(+-)-6-Chloro-a-methylcarbazole-2-acetate	Generator
(+-)-6-Chloro-a-methylcarbazole-2-acetic acid	Generator
(+-)-6-Chloro-alpha-methylcarbazole-2-acetate	Generator
(+-)-6-Chloro-α-methylcarbazole-2-acetate	Generator
(+-)-6-Chloro-α-methylcarbazole-2-acetic acid	Generator
(+/-)-2-(3-chloro-9H-carbazol-7-yl)propanoate	Generator
2-(6-Chloro-9H-carbazol-2-yl)-propionate	Generator
6-Chloro-a-methyl-9H-carbazole-2-acetate	Generator
6-Chloro-a-methyl-9H-carbazole-2-acetic acid	Generator
6-Chloro-alpha-methyl-9H-carbazole-2-acetate	Generator
6-Chloro-α-methyl-9H-carbazole-2-acetate	Generator
6-Chloro-α-methyl-9H-carbazole-2-acetic acid	Generator
2-(6-Chloro-9H-carbazol-2-yl)propanoic acid	HMDB
6-Chloro-alpha-methylcarbazole-2-acetic acid	HMDB
(R)-Isomer OF carprofen	HMDB
(S)-Isomer OF carprofen	HMDB
Carprofen, (S)-isomer	HMDB
(+-)-Isomer OF carprofen	HMDB
Carprofen, (+-)-isomer	HMDB
Carprofen, (R)-isomer	HMDB

Chemical Formula

C₁₅H₁₂ClNO₂

Average Molecular Weight

273.714

Monoisotopic Molecular Weight

273.05565634

IUPAC Name

2-(6-chloro-9H-carbazol-2-yl)propanoic acid

Traditional Name

carprofen

CAS Registry Number

53716-49-7

SMILES

CC(C(O)=O)C1=CC2=C(C=C1)C1=C(N2)C=CC(Cl)=C1

InChI Identifier

InChI=1S/C15H12ClNO2/c1-8(15(18)19)9-2-4-11-12-7-10(16)3-5-13(12)17-14(11)6-9/h2-8,17H,1H3,(H,18,19)

InChI Key

PUXBGTOOZJQSKH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Indole
Aryl chloride
Aryl halide
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organochloride
Organohalogen compound
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:364453 )
carbazoles (CHEBI:364453 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	197.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0038 g/L	Not Available
LogP	3.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0038 g/L	ALOGPS
logP	4.09	ALOGPS
logP	3.88	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.42	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.16 m³·mol⁻¹	ChemAxon
Polarizability	28.56 Å³	ChemAxon
Number of Rings	3	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]+	165.903	30932474
DeepCCS	[M-H]-	163.544	30932474
DeepCCS	[M-2H]-	196.431	30932474
DeepCCS	[M+Na]+	171.996	30932474
AllCCS	[M+H]+	160.3	32859911
AllCCS	[M+H-H2O]+	156.5	32859911
AllCCS	[M+NH4]+	163.8	32859911
AllCCS	[M+Na]+	164.8	32859911
AllCCS	[M-H]-	161.5	32859911
AllCCS	[M+Na-2H]-	160.8	32859911
AllCCS	[M+HCOO]-	160.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.07 minutes	32390414
Predicted by Siyang on May 30, 2022	16.1452 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carprofen	CC(C(O)=O)C1=CC2=C(C=C1)C1=C(N2)C=CC(Cl)=C1	3682.6	Standard polar	33892256
Carprofen	CC(C(O)=O)C1=CC2=C(C=C1)C1=C(N2)C=CC(Cl)=C1	2359.7	Standard non polar	33892256
Carprofen	CC(C(O)=O)C1=CC2=C(C=C1)C1=C(N2)C=CC(Cl)=C1	2806.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carprofen,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C2C(=C1)[NH]C1=CC=C(Cl)C=C12	2804.5	Semi standard non polar	33892256
Carprofen,1TMS,isomer #2	CC(C(=O)O)C1=CC=C2C3=CC(Cl)=CC=C3N([Si](C)(C)C)C2=C1	2740.0	Semi standard non polar	33892256
Carprofen,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C2C3=CC(Cl)=CC=C3N([Si](C)(C)C)C2=C1	2804.3	Semi standard non polar	33892256
Carprofen,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C2C3=CC(Cl)=CC=C3N([Si](C)(C)C)C2=C1	2449.3	Standard non polar	33892256
Carprofen,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C2C3=CC(Cl)=CC=C3N([Si](C)(C)C)C2=C1	2758.9	Standard polar	33892256
Carprofen,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C2C(=C1)[NH]C1=CC=C(Cl)C=C12	3013.1	Semi standard non polar	33892256
Carprofen,1TBDMS,isomer #2	CC(C(=O)O)C1=CC=C2C3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C2=C1	2924.8	Semi standard non polar	33892256
Carprofen,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C2C3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C2=C1	3100.7	Semi standard non polar	33892256
Carprofen,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C2C3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C2=C1	2890.5	Standard non polar	33892256
Carprofen,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C2C3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C2=C1	2959.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Carprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-2290000000-8e764c2da7663d646e65	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carprofen GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9066000000-a8e76536064f58e75c0b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carprofen GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carprofen GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carprofen GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carprofen , positive-QTOF	splash10-0006-2910000000-d2961d6d33669b09ac4d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 10V, Positive-QTOF	splash10-00di-0090000000-bbfca556ca844825bcaa	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 20V, Positive-QTOF	splash10-0kdi-0090000000-e1ce007088ba09013079	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 40V, Positive-QTOF	splash10-0ufr-1390000000-fc5022b898e71ff8c6b1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 10V, Negative-QTOF	splash10-00di-0090000000-6740a199277a7baa3bb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 20V, Negative-QTOF	splash10-00b9-0090000000-44c304e6c89130ee3c8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 40V, Negative-QTOF	splash10-0wbc-6790000000-894ded030da574fd900f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 10V, Positive-QTOF	splash10-05fr-0090000000-31993c6f749285c221f5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 20V, Positive-QTOF	splash10-004i-0090000000-7153ca460f92875f99cb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 40V, Positive-QTOF	splash10-004i-0490000000-c63ce88239e47609a5fe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 10V, Negative-QTOF	splash10-004i-0090000000-b0a34778cae3fe8a802d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 20V, Negative-QTOF	splash10-0059-5090000000-3f0a01f697769e871da5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carprofen 40V, Negative-QTOF	splash10-001i-9020000000-95a620ddb1bb04bf15da	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Carprofen Action Pathway		Not Available

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 DB00821	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00821	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00821

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2483

KEGG Compound ID

C18364

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carprofen

METLIN ID

Not Available

PubChem Compound

2581

PDB ID

Not Available

ChEBI ID

364453

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. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Kay-Mugford P, Benn SJ, LaMarre J, Conlon P: In vitro effects of nonsteroidal anti-inflammatory drugs on cyclooxygenase activity in dogs. Am J Vet Res. 2000 Jul;61(7):802-10. [PubMed:10895904 ]
Brideau C, Van Staden C, Chan CC: In vitro effects of cyclooxygenase inhibitors in whole blood of horses, dogs, and cats. Am J Vet Res. 2001 Nov;62(11):1755-60. [PubMed:11703020 ]
Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222 ]
Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. [PubMed:15939622 ]
Narlawar R, Perez Revuelta BI, Haass C, Steiner H, Schmidt B, Baumann K: Scaffold of the cyclooxygenase-2 (COX-2) inhibitor carprofen provides Alzheimer gamma-secretase modulators. J Med Chem. 2006 Dec 28;49(26):7588-91. [PubMed:17181139 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. [PubMed:15939622 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [PubMed:9880528 ]

Showing metabocard for Carprofen (HMDB0014959)

MOL for HMDB0014959 (Carprofen)

3D MOL for HMDB0014959 (Carprofen)

3D SDF for HMDB0014959 (Carprofen)

3D-SDF for HMDB0014959 (Carprofen)

PDB for HMDB0014959 (Carprofen)

3D PDB for HMDB0014959 (Carprofen)

SMILES for HMDB0014959 (Carprofen)

INCHI for HMDB0014959 (Carprofen)

Structure for HMDB0014959 (Carprofen)

3D Structure for HMDB0014959 (Carprofen)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

Transporters

References