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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-06-15 16:53:40 UTC

Update Date

2021-09-14 15:29:55 UTC

HMDB ID

HMDB0060564

Secondary Accession Numbers

HMDB60564

Metabolite Identification

Common Name

Carboxy-ibuprofen

Description

Carboxy-ibuprofen, also known as ibuprofen COOH, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Carboxy-ibuprofen is a weakly acidic compound (based on its pKa). carboxy-ibuprofen can be biosynthesized from 3-hydroxyibuprofen; which is mediated by the enzyme cytochrome P450 2C9. In humans, carboxy-ibuprofen is involved in ibuprofen metabolism pathway. Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) used for relief of symptoms of arthritis, fever, as an analgesic (pain reliever), especially where there is an inflammatory component, and dysmenorrhea. Carboxy-ibuprofen is a metabolite of ibuprofen. Ibuprofen is known to have an antiplatelet effect, though it is relatively mild and somewhat short-lived when compared with aspirin or other better-known antiplatelet drugs.

Structure

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

HMDB0060564
     RDKit          3D
Carboxy-ibuprofen
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.6404   -0.2997   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157    0.2506   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988   -0.9547   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8803   -0.6083   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -0.5516    0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171   -0.2220    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518    0.0662   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744    0.4219   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5482    1.6680    0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1088   -0.6638    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5709   -1.7232    0.7732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4722   -0.5275    0.5095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104    0.0143   -1.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1070   -0.3132   -1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1616    0.9164    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906    2.1321    0.9387 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106    0.1932    2.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6764   -1.1923    0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3817    0.4350   -0.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341   -0.5835   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899    0.9321   -1.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273   -1.7026    0.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.4234   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -0.7727    1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6369   -0.1782    1.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6508    0.6089   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3067    1.5184    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6578    1.8432    0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0804    2.5725    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1412   -0.9325   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7518    0.2352   -2.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214   -0.3569   -2.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794   -0.8019    2.1098 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  7 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 14  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
M  END


  Mrv0541 06151309532D          

 17 17  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060564

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CC1=CC=C(C=C1)C(C)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O4/c1-8(12(14)15)7-10-3-5-11(6-4-10)9(2)13(16)17/h3-6,8-9H,7H2,1-2H3,(H,14,15)(H,16,17)

> <INCHI_KEY>
DIVLBIVDYADZPL-UHFFFAOYSA-N

> <FORMULA>
C13H16O4

> <MOLECULAR_WEIGHT>
236.2637

> <EXACT_MASS>
236.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.702675230839564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[4-(1-carboxyethyl)phenyl]-2-methylpropanoic acid

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.7792836163333328

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.7711548402904835

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9727941406697096

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
62.423200000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[4-(1-carboxyethyl)phenyl]-2-methylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060564
     RDKit          3D
Carboxy-ibuprofen
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.6404   -0.2997   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157    0.2506   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988   -0.9547   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8803   -0.6083   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -0.5516    0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171   -0.2220    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518    0.0662   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744    0.4219   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5482    1.6680    0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1088   -0.6638    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5709   -1.7232    0.7732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4722   -0.5275    0.5095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104    0.0143   -1.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1070   -0.3132   -1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1616    0.9164    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906    2.1321    0.9387 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106    0.1932    2.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6764   -1.1923    0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3817    0.4350   -0.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341   -0.5835   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899    0.9321   -1.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273   -1.7026    0.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.4234   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -0.7727    1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6369   -0.1782    1.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6508    0.6089   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3067    1.5184    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6578    1.8432    0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0804    2.5725    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1412   -0.9325   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7518    0.2352   -2.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214   -0.3569   -2.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794   -0.8019    2.1098 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  7 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 14  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   10                                                       
CONECT    8    1    7   12                                                  
CONECT    9    2   11   13                                                  
CONECT   10    3    4    7                                                  
CONECT   11    5    6    9                                                  
CONECT   12    8   14   15                                                  
CONECT   13    9   16   17                                                  
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0060564
HETATM    1  C1  UNL     1       4.640  -0.300  -0.597  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.216   0.251  -0.448  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.299  -0.955  -0.518  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.880  -0.608  -0.390  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.219  -0.552   0.831  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.117  -0.222   0.916  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.852   0.066  -0.225  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.274   0.422  -0.190  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.548   1.668   0.623  1.00  0.00           C  
HETATM   10  C10 UNL     1      -4.109  -0.664   0.388  1.00  0.00           C  
HETATM   11  O1  UNL     1      -3.571  -1.723   0.773  1.00  0.00           O  
HETATM   12  O2  UNL     1      -5.472  -0.528   0.510  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.210   0.014  -1.445  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.107  -0.313  -1.500  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.162   0.916   0.866  1.00  0.00           C  
HETATM   16  O3  UNL     1       2.891   2.132   0.939  1.00  0.00           O  
HETATM   17  O4  UNL     1       3.411   0.193   2.010  1.00  0.00           O  
HETATM   18  H1  UNL     1       4.676  -1.192   0.066  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.382   0.435  -0.271  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.734  -0.584  -1.668  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.990   0.932  -1.283  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.627  -1.703   0.226  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.467  -1.423  -1.517  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.778  -0.773   1.721  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.637  -0.178   1.885  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.651   0.609  -1.206  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.307   1.518   1.698  1.00  0.00           H  
HETATM   28  H11 UNL     1      -4.658   1.843   0.548  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.080   2.573   0.197  1.00  0.00           H  
HETATM   30  H13 UNL     1      -6.141  -0.932  -0.118  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.752   0.235  -2.380  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.621  -0.357  -2.455  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.279  -0.802   2.110  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   15   21
CONECT    3    4   22   23
CONECT    4    5    5   14
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8   13
CONECT    8    9   10   26
CONECT    9   27   28   29
CONECT   10   11   11   12
CONECT   12   30
CONECT   13   14   14   31
CONECT   14   32
CONECT   15   16   16   17
CONECT   17   33
END

HMDB0060564
     RDKit          3D
Carboxy-ibuprofen
 33 33  0  0  0  0  0  0  0  0999 V2000
    4.6404   -0.2997   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157    0.2506   -0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988   -0.9547   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8803   -0.6083   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -0.5516    0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171   -0.2220    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518    0.0662   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744    0.4219   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5482    1.6680    0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1088   -0.6638    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5709   -1.7232    0.7732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4722   -0.5275    0.5095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104    0.0143   -1.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1070   -0.3132   -1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1616    0.9164    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906    2.1321    0.9387 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106    0.1932    2.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6764   -1.1923    0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3817    0.4350   -0.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341   -0.5835   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899    0.9321   -1.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6273   -1.7026    0.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671   -1.4234   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -0.7727    1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6369   -0.1782    1.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6508    0.6089   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3067    1.5184    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6578    1.8432    0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0804    2.5725    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1412   -0.9325   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7518    0.2352   -2.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6214   -0.3569   -2.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794   -0.8019    2.1098 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  7 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 14  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4'-(2-Carboxypropyl)phenylpropionic acid	ChEBI
2-(4-(2-Carboxypropyl)phenyl)propionic acid	ChEBI
Ibuprofen COOH	ChEBI
2,4'-(2-Carboxypropyl)phenylpropionate	Generator
2-(4-(2-Carboxypropyl)phenyl)propionate	Generator
Carboxy-ibuprofen	ChEBI
Carboxyibuprofen	MeSH

Chemical Formula

C₁₃H₁₆O₄

Average Molecular Weight

236.2637

Monoisotopic Molecular Weight

236.104859

IUPAC Name

3-[4-(1-carboxyethyl)phenyl]-2-methylpropanoic acid

Traditional Name

3-[4-(1-carboxyethyl)phenyl]-2-methylpropanoic acid

CAS Registry Number

Not Available

SMILES

CC(CC1=CC=C(C=C1)C(C)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C13H16O4/c1-8(12(14)15)7-10-3-5-11(6-4-10)9(2)13(16)17/h3-6,8-9H,7H2,1-2H3,(H,14,15)(H,16,17)

InChI Key

DIVLBIVDYADZPL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

2-phenylpropanoic-acid
3-phenylpropanoic-acid
P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Phenylpropane
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060564)
Liver (HMDB: HMDB0060564)

Biofluid or Excreta

Excreta

Feces (PMID: 27543620)
Urine (PMID: 32966057)

Non-excretory biofluid

Blood (PMID: 32966057)

Cellular substructure

Membrane (HMDB: HMDB0060564)
Cytoplasm (HMDB: HMDB0060564)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ibuprofen Action Pathway (PathBank: SMP0000086)

Metabolic pathway

Ibuprofen Metabolism Pathway (PathBank: SMP0000590)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	2.29	ALOGPS
logP	2.78	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.97	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.42 m³·mol⁻¹	ChemAxon
Polarizability	24.7 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
DarkChem	[M+H]+	156.336	31661259
DarkChem	[M-H]-	152.376	31661259
DeepCCS	[M+H]+	153.141	30932474
DeepCCS	[M-H]-	150.783	30932474
DeepCCS	[M-2H]-	183.82	30932474
DeepCCS	[M+Na]+	159.234	30932474
AllCCS	[M+H]+	153.9	32859911
AllCCS	[M+H-H2O]+	150.1	32859911
AllCCS	[M+NH4]+	157.4	32859911
AllCCS	[M+Na]+	158.5	32859911
AllCCS	[M-H]-	156.1	32859911
AllCCS	[M+Na-2H]-	156.5	32859911
AllCCS	[M+HCOO]-	157.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carboxy-ibuprofen	CC(CC1=CC=C(C=C1)C(C)C(O)=O)C(O)=O	3371.8	Standard polar	33892256
Carboxy-ibuprofen	CC(CC1=CC=C(C=C1)C(C)C(O)=O)C(O)=O	1837.4	Standard non polar	33892256
Carboxy-ibuprofen	CC(CC1=CC=C(C=C1)C(C)C(O)=O)C(O)=O	2005.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carboxy-ibuprofen,1TMS,isomer #1	CC(CC1=CC=C(C(C)C(=O)O[Si](C)(C)C)C=C1)C(=O)O	1949.0	Semi standard non polar	33892256
Carboxy-ibuprofen,1TMS,isomer #2	CC(CC1=CC=C(C(C)C(=O)O)C=C1)C(=O)O[Si](C)(C)C	1964.8	Semi standard non polar	33892256
Carboxy-ibuprofen,2TMS,isomer #1	CC(CC1=CC=C(C(C)C(=O)O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	1981.4	Semi standard non polar	33892256
Carboxy-ibuprofen,1TBDMS,isomer #1	CC(CC1=CC=C(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	2200.5	Semi standard non polar	33892256
Carboxy-ibuprofen,1TBDMS,isomer #2	CC(CC1=CC=C(C(C)C(=O)O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2235.6	Semi standard non polar	33892256
Carboxy-ibuprofen,2TBDMS,isomer #1	CC(CC1=CC=C(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2465.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Carboxy-ibuprofen EI-B (Non-derivatized)	splash10-029y-9000000000-c80bec974f28638c0ef3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Carboxy-ibuprofen EI-B (Non-derivatized)	splash10-029y-9000000000-c80bec974f28638c0ef3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carboxy-ibuprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kg-1910000000-67160596c417008327e9	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carboxy-ibuprofen GC-MS (2 TMS) - 70eV, Positive	splash10-022m-9283000000-0efcd729a3f3c7d7edf2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carboxy-ibuprofen 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 - Carboxy-ibuprofen 35V, Positive-QTOF	splash10-0006-0910000000-c2827168498a4962ac86	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carboxy-ibuprofen 35V, Negative-QTOF	splash10-00di-9100000000-5383e1959b406038f21a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 10V, Positive-QTOF	splash10-00ku-0890000000-09c6cf9139f4b24b5595	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 20V, Positive-QTOF	splash10-014l-1920000000-840272a444f21fad8bd7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 40V, Positive-QTOF	splash10-00kb-1900000000-8142fc0197c65242ac9c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 10V, Negative-QTOF	splash10-000i-0590000000-ef703bcd0ae31b3c6858	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 20V, Negative-QTOF	splash10-000g-0920000000-6adff5ecdf1de0c84c84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 40V, Negative-QTOF	splash10-00xs-7900000000-13b3f512d747eb0400e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 10V, Positive-QTOF	splash10-014i-0890000000-661f246b92748cdf71ad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 20V, Positive-QTOF	splash10-015d-0920000000-78e23a387b076915da3e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 40V, Positive-QTOF	splash10-0gb9-1900000000-da77016d411c40f24620	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 10V, Negative-QTOF	splash10-000l-0790000000-6d8f4e25e001b4124512	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 20V, Negative-QTOF	splash10-0002-0900000000-d35ab8e1327b17e568e9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxy-ibuprofen 40V, Negative-QTOF	splash10-014i-0900000000-7aaf8622cd9f39155d7f	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Ibuprofen Action Pathway		Not Available
Ibuprofen Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10444113

PDB ID

Not Available

ChEBI ID

133199

Food Biomarker Ontology

Not Available

VMH ID

CARIBUP_R

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Tan SC, Baker JA, Stevens N, deBiasi V, Salter C, Chalaux M, Afarinkia K, Hutt AJ: Synthesis, chromatographic resolution and chiroptical properties of carboxyibuprofen stereoisomers: major metabolites of ibuprofen in man. Chirality. 1997;9(1):75-87. [PubMed:9094205 ]

Showing metabocard for Carboxy-ibuprofen (HMDB0060564)

MOL for HMDB0060564 (Carboxy-ibuprofen)

3D MOL for HMDB0060564 (Carboxy-ibuprofen)

3D SDF for HMDB0060564 (Carboxy-ibuprofen)

3D-SDF for HMDB0060564 (Carboxy-ibuprofen)

PDB for HMDB0060564 (Carboxy-ibuprofen)

3D PDB for HMDB0060564 (Carboxy-ibuprofen)

SMILES for HMDB0060564 (Carboxy-ibuprofen)

INCHI for HMDB0060564 (Carboxy-ibuprofen)

Structure for HMDB0060564 (Carboxy-ibuprofen)

3D Structure for HMDB0060564 (Carboxy-ibuprofen)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra