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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

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

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

Excreta

Biofluid or Excreta

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

Cellular substructure

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

Source

Endogenous

Endogenous (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 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.	5.74 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8054 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.39 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1705.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	302.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	89.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	424.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	478.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	940.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	458.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1141.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	278.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	322.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	210.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	76.5 seconds	40023050

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

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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 Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized