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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-07-09 16:07:18 UTC

Update Date

2021-09-14 15:02:27 UTC

HMDB ID

HMDB0060920

Secondary Accession Numbers

HMDB0060698
HMDB60698
HMDB60920

Metabolite Identification

Common Name

2-Hydroxyibuprofen

Description

2-Hydroxyibuprofen, also known as ibuprofen OH, 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. 2-Hydroxyibuprofen is a metabolite of ibuprofen. 2-Hydroxyibuprofen is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-hydroxyibuprofen can be biosynthesized from ibuprofen through the action of the enzymes cytochrome P450 3A4, cytochrome P450 2C8, cytochrome P450 2C19, and cytochrome P450 2C9. In humans, 2-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. 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

HMDB0060920
     RDKit          3D
2-Hydroxyibuprofen
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.1960   -0.5457    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -0.3978   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209    0.8582   -1.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2423    0.8584   -2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4922    2.1140   -0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -0.4763   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    0.4722    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0461    0.4063    0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8159   -0.6164    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715   -0.7542    0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012   -0.0298   -0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7350    1.4549   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5613   -0.1216    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8987   -0.5024   -1.5749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1909   -1.5685   -0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552   -1.5019   -0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -0.0787    1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931   -0.0635    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3934   -1.6126    1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6745   -1.2419   -1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    2.5861   -0.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269    1.2761    1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    1.1502    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910   -1.8179    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5529   -0.3439    1.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6538    1.5369   -0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8741    1.8816    0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3008    2.0181   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1375   -0.7358   -0.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0532    0.8768    0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6647   -0.6147    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5134    0.1580   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7650   -2.3705   -0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6165   -2.2536   -1.2537 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  1  0
 11 12  1  0
 11 13  1  0
 11 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
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 13 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
    0.0000    2.4750    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
    0.4125   -2.3645    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
    0.7145    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
    0.0000   -1.6500    0.0000 C   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
   -0.4125   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  1  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060920

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O3/c1-9(12(14)15)11-6-4-10(5-7-11)8-13(2,3)16/h4-7,9,16H,8H2,1-3H3,(H,14,15)

> <INCHI_KEY>
UJHKVYPPCJBOSG-UHFFFAOYSA-N

> <FORMULA>
C13H18O3

> <MOLECULAR_WEIGHT>
222.2802

> <EXACT_MASS>
222.125594442

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.482716928369143

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.372443514333333

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.283368276264188

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6298261596028425

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6749858368130353

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
62.568000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060920
     RDKit          3D
2-Hydroxyibuprofen
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.1960   -0.5457    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -0.3978   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209    0.8582   -1.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2423    0.8584   -2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4922    2.1140   -0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -0.4763   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    0.4722    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0461    0.4063    0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8159   -0.6164    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715   -0.7542    0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012   -0.0298   -0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7350    1.4549   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5613   -0.1216    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8987   -0.5024   -1.5749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1909   -1.5685   -0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552   -1.5019   -0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -0.0787    1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931   -0.0635    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3934   -1.6126    1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6745   -1.2419   -1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    2.5861   -0.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269    1.2761    1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    1.1502    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910   -1.8179    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5529   -0.3439    1.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6538    1.5369   -0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8741    1.8816    0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3008    2.0181   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1375   -0.7358   -0.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0532    0.8768    0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6647   -0.6147    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5134    0.1580   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7650   -2.3705   -0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6165   -2.2536   -1.2537 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  1  0
 11 12  1  0
 11 13  1  0
 11 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
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 13 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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -4.414   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.770  -1.746   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4    6   10                                                       
CONECT    5    7   10                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8   10   13                                                       
CONECT    9    1   11   12                                                  
CONECT   10    4    5    8                                                  
CONECT   11    6    7    9                                                  
CONECT   12    9   14   15                                                  
CONECT   13    2    3    8   16                                             
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0060920
HETATM    1  C1  UNL     1       4.196  -0.546   0.858  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.371  -0.398  -0.414  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.721   0.858  -1.117  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.242   0.858  -2.262  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.492   2.114  -0.549  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.918  -0.476  -0.111  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.320   0.472   0.686  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.046   0.406   0.977  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.816  -0.616   0.466  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.271  -0.754   0.729  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.101  -0.030  -0.305  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.735   1.455  -0.273  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.561  -0.122   0.079  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.899  -0.502  -1.575  1.00  0.00           O  
HETATM   15  C12 UNL     1      -0.191  -1.568  -0.340  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.155  -1.502  -0.625  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.708  -0.079   1.730  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.193  -0.063   0.743  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.393  -1.613   1.085  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.675  -1.242  -1.067  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.319   2.586  -0.179  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.927   1.276   1.087  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.521   1.150   1.603  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.591  -1.818   0.722  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.553  -0.344   1.732  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.654   1.537  -0.511  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.874   1.882   0.749  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.301   2.018  -1.021  1.00  0.00           H  
HETATM   29  H13 UNL     1      -5.137  -0.736  -0.654  1.00  0.00           H  
HETATM   30  H14 UNL     1      -5.053   0.877   0.123  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.665  -0.615   1.061  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.513   0.158  -2.185  1.00  0.00           H  
HETATM   33  H17 UNL     1      -0.765  -2.370  -0.748  1.00  0.00           H  
HETATM   34  H18 UNL     1       1.616  -2.254  -1.254  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    6   20
CONECT    3    4    4    5
CONECT    5   21
CONECT    6    7    7   16
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10   15
CONECT   10   11   24   25
CONECT   11   12   13   14
CONECT   12   26   27   28
CONECT   13   29   30   31
CONECT   14   32
CONECT   15   16   16   33
CONECT   16   34
END

HMDB0060920
     RDKit          3D
2-Hydroxyibuprofen
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.1960   -0.5457    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -0.3978   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209    0.8582   -1.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2423    0.8584   -2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4922    2.1140   -0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -0.4763   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    0.4722    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0461    0.4063    0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8159   -0.6164    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715   -0.7542    0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012   -0.0298   -0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7350    1.4549   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5613   -0.1216    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8987   -0.5024   -1.5749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1909   -1.5685   -0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552   -1.5019   -0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -0.0787    1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931   -0.0635    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3934   -1.6126    1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6745   -1.2419   -1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    2.5861   -0.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269    1.2761    1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    1.1502    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910   -1.8179    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5529   -0.3439    1.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6538    1.5369   -0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8741    1.8816    0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3008    2.0181   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1375   -0.7358   -0.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0532    0.8768    0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6647   -0.6147    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5134    0.1580   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7650   -2.3705   -0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6165   -2.2536   -1.2537 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  1  0
 11 12  1  0
 11 13  1  0
 11 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
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4'-(2-Hydroxy-2-methylpropyl)phenylpropionic acid	ChEBI
Hydroxyibuprofen	ChEBI
Ibuprofen OH	ChEBI
2,4'-(2-Hydroxy-2-methylpropyl)phenylpropionate	Generator

Chemical Formula

C₁₃H₁₈O₃

Average Molecular Weight

222.2802

Monoisotopic Molecular Weight

222.125594442

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H18O3/c1-9(12(14)15)11-6-4-10(5-7-11)8-13(2,3)16/h4-7,9,16H,8H2,1-3H3,(H,14,15)

InChI Key

UJHKVYPPCJBOSG-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
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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 (HMDB: HMDB0060920)

Organ

Kidney (HMDB: HMDB0060920)
Liver (HMDB: HMDB0060920)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060920)
Feces (PMID: 25037050)

Cellular substructure

Cytoplasm (HMDB: HMDB0060920)
Membrane (HMDB: HMDB0060920)

Source

Endogenous

Endogenous (HMDB: HMDB0060920)

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	2.41	ALOGPS
logP	2.37	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.63	ChemAxon
pKa (Strongest Basic)	-2.7	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	4	ChemAxon
Refractivity	62.57 m³·mol⁻¹	ChemAxon
Polarizability	24.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.142	31661259
DarkChem	[M-H]-	149.638	31661259
DeepCCS	[M+H]+	153.906	30932474
DeepCCS	[M-H]-	151.524	30932474
DeepCCS	[M-2H]-	184.485	30932474
DeepCCS	[M+Na]+	159.975	30932474
AllCCS	[M+H]+	150.6	32859911
AllCCS	[M+H-H2O]+	146.7	32859911
AllCCS	[M+NH4]+	154.2	32859911
AllCCS	[M+Na]+	155.2	32859911
AllCCS	[M-H]-	154.4	32859911
AllCCS	[M+Na-2H]-	155.0	32859911
AllCCS	[M+HCOO]-	155.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyibuprofen	CC(C(O)=O)C1=CC=C(CC(C)(C)O)C=C1	3167.0	Standard polar	33892256
2-Hydroxyibuprofen	CC(C(O)=O)C1=CC=C(CC(C)(C)O)C=C1	1716.9	Standard non polar	33892256
2-Hydroxyibuprofen	CC(C(O)=O)C1=CC=C(CC(C)(C)O)C=C1	1796.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxyibuprofen,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C(CC(C)(C)O)C=C1	1800.3	Semi standard non polar	33892256
2-Hydroxyibuprofen,1TMS,isomer #2	CC(C(=O)O)C1=CC=C(CC(C)(C)O[Si](C)(C)C)C=C1	1858.7	Semi standard non polar	33892256
2-Hydroxyibuprofen,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C(CC(C)(C)O[Si](C)(C)C)C=C1	1850.4	Semi standard non polar	33892256
2-Hydroxyibuprofen,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(CC(C)(C)O)C=C1	2056.4	Semi standard non polar	33892256
2-Hydroxyibuprofen,1TBDMS,isomer #2	CC(C(=O)O)C1=CC=C(CC(C)(C)O[Si](C)(C)C(C)(C)C)C=C1	2134.1	Semi standard non polar	33892256
2-Hydroxyibuprofen,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(CC(C)(C)O[Si](C)(C)C(C)(C)C)C=C1	2353.7	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 - 2-Hydroxyibuprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-4910000000-230705a3b25bc8d2bbd7	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxyibuprofen GC-MS (2 TMS) - 70eV, Positive	splash10-00ai-9682000000-0111491ba4a88d97341e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-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 - 2-Hydroxyibuprofen 10V, Positive-QTOF	splash10-0a4i-0690000000-9318a4a4877cd81cd175	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 20V, Positive-QTOF	splash10-0a4i-0930000000-ea94bba1900c2d2c4529	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 40V, Positive-QTOF	splash10-0a4i-0900000000-d16bf512545d34c8d478	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 10V, Negative-QTOF	splash10-00di-0590000000-ad78ab3a996915e1bec9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 20V, Negative-QTOF	splash10-0629-1940000000-3d114bfd3f6171882588	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 40V, Negative-QTOF	splash10-00e9-6900000000-3ca6784a37e019ab2e84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 10V, Positive-QTOF	splash10-0ab9-0790000000-5c8adbb84285c2241070	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 20V, Positive-QTOF	splash10-0a4i-3930000000-0cd0c4bb51413af43df4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 40V, Positive-QTOF	splash10-066r-3900000000-0012c7f4f8fb1485e018	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 10V, Negative-QTOF	splash10-00di-0090000000-a6828934a3d2ae50a370	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 20V, Negative-QTOF	splash10-0ab9-7920000000-b9e1c33ee4e9c702d996	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxyibuprofen 40V, Negative-QTOF	splash10-0a4l-9700000000-956637591fe570c8af76	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

10443535

PDB ID

Not Available

ChEBI ID

133197

Food Biomarker Ontology

Not Available

VMH ID

2HIBUP_R

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. 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

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

Showing metabocard for 2-Hydroxyibuprofen (HMDB0060920)

MOL for HMDB0060920 (2-Hydroxyibuprofen)

3D MOL for HMDB0060920 (2-Hydroxyibuprofen)

3D SDF for HMDB0060920 (2-Hydroxyibuprofen)

3D-SDF for HMDB0060920 (2-Hydroxyibuprofen)

PDB for HMDB0060920 (2-Hydroxyibuprofen)

3D PDB for HMDB0060920 (2-Hydroxyibuprofen)

SMILES for HMDB0060920 (2-Hydroxyibuprofen)

INCHI for HMDB0060920 (2-Hydroxyibuprofen)

Structure for HMDB0060920 (2-Hydroxyibuprofen)

3D Structure for HMDB0060920 (2-Hydroxyibuprofen)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions