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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-07-09 16:07:21 UTC

Update Date

2021-09-14 15:15:55 UTC

HMDB ID

HMDB0060921

Secondary Accession Numbers

HMDB60921

Metabolite Identification

Common Name

3-Hydroxyibuprofen

Description

3-Hydroxyibuprofen 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. 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. 3-Hydroxyibuprofen is a metabolite of ibuprofen. 3-Hydroxyibuprofen is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 3-hydroxyibuprofen participates in a number of enzymatic reactions. In particular, 3-hydroxyibuprofen can be biosynthesized from ibuprofen through its interaction with the enzymes cytochrome P450 2C9, cytochrome P450 2C19, and cytochrome P450 2C8. In addition, 3-hydroxyibuprofen can be converted into carboxy-ibuprofen; which is mediated by the enzyme cytochrome P450 2C9. In humans, 3-hydroxyibuprofen 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.

Structure

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

HMDB0060921
     RDKit          3D
3-Hydroxyibuprofen
 34 34  0  0  0  0  0  0  0  0999 V2000
   -2.8859   -1.7065   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1721   -0.2580    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9913    0.6119   -1.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8465    0.2133   -2.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3317    0.2342    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845    0.1359    0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2179    1.1904    0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1422    1.1512    0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8668    0.0266    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250    0.0066    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737    1.0960    0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4910    0.0871   -1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1084    1.0076   -1.9127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -0.9154   -2.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2297   -1.0453    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328   -0.9732    1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9300   -2.2421    0.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6366   -2.1869   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8597   -1.7939   -0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354   -0.1713    0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    1.6442   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235    0.5616   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174    0.6646   -2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704    1.2593    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -0.4029    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039    2.0683    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    2.0200   -0.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350   -0.9677    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5489    2.0710    0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0404    1.2491    0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3064    0.8296    1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -1.7038   -2.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029   -1.9417    1.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6191   -1.8198    1.7257 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
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  9 15  1  0
 15 16  2  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END


  Mrv0541 07091309072D          

 16 16  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   -2.4750    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
    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
    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
  9  1  1  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060921

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O3/c1-9(8-14)7-11-3-5-12(6-4-11)10(2)13(15)16/h3-6,9-10,14H,7-8H2,1-2H3,(H,15,16)

> <INCHI_KEY>
HFAIHLSDLUYLQA-UHFFFAOYSA-N

> <FORMULA>
C13H18O3

> <MOLECULAR_WEIGHT>
222.2802

> <EXACT_MASS>
222.125594442

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.811633882765026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[4-(3-hydroxy-2-methylpropyl)phenyl]propanoic acid

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.484833312666667

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.469308579106908

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.574542984126096

> <JCHEM_PKA_STRONGEST_BASIC>
-2.593524427512784

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
62.58360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[4-(3-hydroxy-2-methylpropyl)phenyl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060921
     RDKit          3D
3-Hydroxyibuprofen
 34 34  0  0  0  0  0  0  0  0999 V2000
   -2.8859   -1.7065   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1721   -0.2580    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9913    0.6119   -1.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8465    0.2133   -2.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3317    0.2342    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845    0.1359    0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2179    1.1904    0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1422    1.1512    0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8668    0.0266    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250    0.0066    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737    1.0960    0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4910    0.0871   -1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1084    1.0076   -1.9127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -0.9154   -2.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2297   -1.0453    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328   -0.9732    1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9300   -2.2421    0.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6366   -2.1869   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8597   -1.7939   -0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354   -0.1713    0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    1.6442   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235    0.5616   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174    0.6646   -2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704    1.2593    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -0.4029    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039    2.0683    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    2.0200   -0.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350   -0.9677    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5489    2.0710    0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0404    1.2491    0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3064    0.8296    1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -1.7038   -2.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029   -1.9417    1.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6191   -1.8198    1.7257 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
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  9 15  1  0
 15 16  2  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-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  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   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       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    5   11                                                       
CONECT    4    6   11                                                       
CONECT    5    3   12                                                       
CONECT    6    4   12                                                       
CONECT    7    9   11                                                       
CONECT    8    9   14                                                       
CONECT    9    1    7    8                                                  
CONECT   10    2   12   13                                                  
CONECT   11    3    4    7                                                  
CONECT   12    5    6   10                                                  
CONECT   13   10   15   16                                                  
CONECT   14    8                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0060921
HETATM    1  C1  UNL     1      -2.886  -1.707  -0.238  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.172  -0.258   0.051  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.991   0.612  -1.175  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.846   0.213  -2.193  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.332   0.234   1.183  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.885   0.136   0.934  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.218   1.190   0.345  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.142   1.151   0.089  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.867   0.027   0.429  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.325   0.007   0.145  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.074   1.096   0.861  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.491   0.087  -1.325  1.00  0.00           C  
HETATM   13  O2  UNL     1       4.108   1.008  -1.913  1.00  0.00           O  
HETATM   14  O3  UNL     1       2.930  -0.915  -2.099  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.230  -1.045   1.020  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.133  -0.973   1.262  1.00  0.00           C  
HETATM   17  H1  UNL     1      -2.930  -2.242   0.743  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.637  -2.187  -0.882  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.860  -1.794  -0.606  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.235  -0.171   0.356  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.271   1.644  -0.880  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.924   0.562  -1.465  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.717   0.665  -2.044  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.670   1.259   1.442  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.583  -0.403   2.079  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.804   2.068   0.084  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.611   2.020  -0.380  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.735  -0.968   0.484  1.00  0.00           H  
HETATM   29  H13 UNL     1       3.549   2.071   0.835  1.00  0.00           H  
HETATM   30  H14 UNL     1       5.040   1.249   0.311  1.00  0.00           H  
HETATM   31  H15 UNL     1       4.306   0.830   1.905  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.502  -1.704  -2.379  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.803  -1.942   1.292  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.619  -1.820   1.726  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    5   20
CONECT    3    4   21   22
CONECT    4   23
CONECT    5    6   24   25
CONECT    6    7    7   16
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   15
CONECT   10   11   12   28
CONECT   11   29   30   31
CONECT   12   13   13   14
CONECT   14   32
CONECT   15   16   16   33
CONECT   16   34
END

HMDB0060921
     RDKit          3D
3-Hydroxyibuprofen
 34 34  0  0  0  0  0  0  0  0999 V2000
   -2.8859   -1.7065   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1721   -0.2580    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9913    0.6119   -1.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8465    0.2133   -2.1926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3317    0.2342    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8845    0.1359    0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2179    1.1904    0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1422    1.1512    0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8668    0.0266    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250    0.0066    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0737    1.0960    0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4910    0.0871   -1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1084    1.0076   -1.9127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -0.9154   -2.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2297   -1.0453    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328   -0.9732    1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9300   -2.2421    0.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6366   -2.1869   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8597   -1.7939   -0.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354   -0.1713    0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713    1.6442   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235    0.5616   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174    0.6646   -2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704    1.2593    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -0.4029    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039    2.0683    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    2.0200   -0.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350   -0.9677    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5489    2.0710    0.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0404    1.2491    0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3064    0.8296    1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -1.7038   -2.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029   -1.9417    1.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6191   -1.8198    1.7257 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
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  9 15  1  0
 15 16  2  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈O₃

Average Molecular Weight

222.2802

Monoisotopic Molecular Weight

222.125594442

IUPAC Name

2-[4-(3-hydroxy-2-methylpropyl)phenyl]propanoic acid

Traditional Name

2-[4-(3-hydroxy-2-methylpropyl)phenyl]propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H18O3/c1-9(8-14)7-11-3-5-12(6-4-11)10(2)13(15)16/h3-6,9-10,14H,7-8H2,1-2H3,(H,15,16)

InChI Key

HFAIHLSDLUYLQA-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
P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Phenylpropane
Monocyclic benzene moiety
Benzenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

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	0.32 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.48	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.58 m³·mol⁻¹	ChemAxon
Polarizability	24.81 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]+	153.317	31661259
DarkChem	[M-H]-	151.465	31661259
DeepCCS	[M+H]+	153.465	30932474
DeepCCS	[M-H]-	150.772	30932474
DeepCCS	[M-2H]-	186.161	30932474
DeepCCS	[M+Na]+	161.949	30932474
AllCCS	[M+H]+	151.2	32859911
AllCCS	[M+H-H2O]+	147.3	32859911
AllCCS	[M+NH4]+	154.8	32859911
AllCCS	[M+Na]+	155.9	32859911
AllCCS	[M-H]-	155.0	32859911
AllCCS	[M+Na-2H]-	155.6	32859911
AllCCS	[M+HCOO]-	156.4	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.	5.85 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3875 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.33 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1854.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	338.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	112.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	506.1 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	532.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1011.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	467.0 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	1302.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	301.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	207.1 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	24.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyibuprofen	CC(CO)CC1=CC=C(C=C1)C(C)C(O)=O	3486.8	Standard polar	33892256
3-Hydroxyibuprofen	CC(CO)CC1=CC=C(C=C1)C(C)C(O)=O	1826.0	Standard non polar	33892256
3-Hydroxyibuprofen	CC(CO)CC1=CC=C(C=C1)C(C)C(O)=O	1876.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyibuprofen,1TMS,isomer #1	CC(CO[Si](C)(C)C)CC1=CC=C(C(C)C(=O)O)C=C1	1896.4	Semi standard non polar	33892256
3-Hydroxyibuprofen,1TMS,isomer #2	CC(CO)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C)C=C1	1869.8	Semi standard non polar	33892256
3-Hydroxyibuprofen,2TMS,isomer #1	CC(CO[Si](C)(C)C)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C)C=C1	1879.6	Semi standard non polar	33892256
3-Hydroxyibuprofen,1TBDMS,isomer #1	CC(CO[Si](C)(C)C(C)(C)C)CC1=CC=C(C(C)C(=O)O)C=C1	2158.4	Semi standard non polar	33892256
3-Hydroxyibuprofen,1TBDMS,isomer #2	CC(CO)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1	2118.4	Semi standard non polar	33892256
3-Hydroxyibuprofen,2TBDMS,isomer #1	CC(CO[Si](C)(C)C(C)(C)C)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1	2347.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyibuprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xs-1910000000-faafb3e6e981c8bed49e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyibuprofen GC-MS (2 TMS) - 70eV, Positive	splash10-0fg9-6492000000-93d58754b353e3f668f0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyibuprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyibuprofen 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 10V, Positive-QTOF	splash10-0ab9-0590000000-6ba17ecc017cd89a329a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 20V, Positive-QTOF	splash10-0a4i-1930000000-621b8c2cc30713fa687d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 40V, Positive-QTOF	splash10-0aos-3900000000-32ad63b7b1b422462aa7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 10V, Negative-QTOF	splash10-00di-0390000000-b124c0f38802019877aa	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 20V, Negative-QTOF	splash10-05i0-0950000000-8c00977ae4c9d74b14ed	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 40V, Negative-QTOF	splash10-05mk-6900000000-b843e046ba2a268adacb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 10V, Positive-QTOF	splash10-0a6r-0960000000-e33bf7c9cfc7ebbd3d54	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 20V, Positive-QTOF	splash10-0a5i-0920000000-5afbcf27502ad97f56b1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 40V, Positive-QTOF	splash10-0a4i-1900000000-7ce6d6b61dbc558517ea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 10V, Negative-QTOF	splash10-00di-0090000000-e5cd496528956fe125ac	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 20V, Negative-QTOF	splash10-0002-0920000000-dab699c3f3b1957f2c1b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyibuprofen 40V, Negative-QTOF	splash10-014i-1900000000-0870f9e15374a842ad52	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	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

71312545

PDB ID

Not Available

ChEBI ID

Not Available

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. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

3-Hydroxyibuprofen → 2-{4-[2-methyl-3-(sulfooxy)propyl]phenyl}propanoic acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

3-Hydroxyibuprofen → 6-{3-[4-(1-carboxyethyl)phenyl]-2-methylpropoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
3-Hydroxyibuprofen → 3,4,5-trihydroxy-6-({2-[4-(3-hydroxy-2-methylpropyl)phenyl]propanoyl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for 3-Hydroxyibuprofen (HMDB0060921)

MOL for HMDB0060921 (3-Hydroxyibuprofen)

3D MOL for HMDB0060921 (3-Hydroxyibuprofen)

3D SDF for HMDB0060921 (3-Hydroxyibuprofen)

3D-SDF for HMDB0060921 (3-Hydroxyibuprofen)

PDB for HMDB0060921 (3-Hydroxyibuprofen)

3D PDB for HMDB0060921 (3-Hydroxyibuprofen)

SMILES for HMDB0060921 (3-Hydroxyibuprofen)

INCHI for HMDB0060921 (3-Hydroxyibuprofen)

Structure for HMDB0060921 (3-Hydroxyibuprofen)

3D Structure for HMDB0060921 (3-Hydroxyibuprofen)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions