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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:25:34 UTC

Update Date

2021-09-14 15:45:32 UTC

HMDB ID

HMDB0060647

Secondary Accession Numbers

HMDB60647

Metabolite Identification

Common Name

4-hydroxy ketorolac

Description

4-hydroxy ketorolac is a metabolite of ketorolac. Ketorolac or ketorolac tromethamine (marketed under the trademarks Toradol and Acular in the US, where generics have also been approved, and various other brand names 'Minolac' {ACI Pharmaceuticals} around the world) is a non-steroidal anti-inflammatory drug (NSAID) in the family of heterocyclic acetic acid derivatives, often used as an analgesic. Ketorolac acts by inhibiting the bodily synthesis of prostaglandins. (Wikipedia)

Structure

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

HMDB0060647
     RDKit          3D
4-hydroxy ketorolac
 33 35  0  0  0  0  0  0  0  0999 V2000
    1.2776   -2.2863   -0.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1380   -1.0041   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3332   -0.2736   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3787   -0.9303    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5378   -0.2958    0.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795    1.0410    0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8508    1.6831    0.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835    1.7073   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    1.0498   -0.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1797   -0.4655   -0.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321    0.4965   -1.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9062    0.7242   -1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -0.1253   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444   -0.8186   -0.2030 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7935   -1.7403    0.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576   -1.0323    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6333   -0.5546    0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670    0.5836    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7066    0.4811   -0.3261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113    1.7179    0.8947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2673   -1.9706    0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430   -0.8201    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5909    1.2122    1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7796    2.7487   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428    1.6022   -0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110    1.0191   -2.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808    1.4257   -2.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0501   -1.8609    1.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128   -2.6583    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.1239    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7160   -1.7280    1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -1.4051   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6869    2.6014    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9  3  1  0
 14 10  1  0
 17 13  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 20 33  1  0
M  END

  Mrv0541 06151311252D          

 20 22  0  0  0  0            999 V2000
   -1.0619    0.9561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971    1.3977    0.0000 O   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
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721   -2.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -3.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751   -4.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -4.5719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0869   -3.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652   -2.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060647

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H13NO4/c17-10-3-1-9(2-4-10)14(18)13-6-5-12-11(15(19)20)7-8-16(12)13/h1-6,11,17H,7-8H2,(H,19,20)

> <INCHI_KEY>
PIQMOWBWPFGZMW-UHFFFAOYSA-N

> <FORMULA>
C15H13NO4

> <MOLECULAR_WEIGHT>
271.268

> <EXACT_MASS>
271.084457909

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.86435305907013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(4-hydroxybenzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
1.9797976419999999

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.783174698457782

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6772030078026168

> <JCHEM_PKA_STRONGEST_BASIC>
-6.9389789512897595

> <JCHEM_POLAR_SURFACE_AREA>
79.53

> <JCHEM_REFRACTIVITY>
72.17540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(4-hydroxybenzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060647
     RDKit          3D
4-hydroxy ketorolac
 33 35  0  0  0  0  0  0  0  0999 V2000
    1.2776   -2.2863   -0.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1380   -1.0041   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3332   -0.2736   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3787   -0.9303    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5378   -0.2958    0.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795    1.0410    0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8508    1.6831    0.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835    1.7073   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    1.0498   -0.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1797   -0.4655   -0.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321    0.4965   -1.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9062    0.7242   -1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -0.1253   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444   -0.8186   -0.2030 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7935   -1.7403    0.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576   -1.0323    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6333   -0.5546    0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670    0.5836    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7066    0.4811   -0.3261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113    1.7179    0.8947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2673   -1.9706    0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430   -0.8201    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5909    1.2122    1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7796    2.7487   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428    1.6022   -0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110    1.0191   -2.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808    1.4257   -2.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0501   -1.8609    1.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128   -2.6583    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.1239    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7160   -1.7280    1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -1.4051   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6869    2.6014    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9  3  1  0
 14 10  1  0
 17 13  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 20 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  O   UNK     0      -1.982   1.785   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.476   1.465   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.555   2.609   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.465  -2.016   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.835  -1.246   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.405  -3.956   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.912  -4.277   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.375  -5.101   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.851  -6.565   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.820  -7.710   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.314  -7.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.717  -8.534   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.162  -5.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.868  -4.781   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    4    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0060647
HETATM    1  O1  UNL     1       1.278  -2.286  -0.588  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.138  -1.004  -0.535  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.333  -0.274  -0.188  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.379  -0.930   0.485  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.538  -0.296   0.859  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.679   1.041   0.560  1.00  0.00           C  
HETATM    7  O2  UNL     1       5.851   1.683   0.937  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.684   1.707  -0.092  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.531   1.050  -0.456  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.180  -0.466  -0.823  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.532   0.496  -1.729  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.906   0.724  -1.655  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.373  -0.125  -0.683  1.00  0.00           C  
HETATM   14  N1  UNL     1      -1.344  -0.819  -0.203  1.00  0.00           N  
HETATM   15  C12 UNL     1      -1.794  -1.740   0.842  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.058  -1.032   1.348  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.633  -0.555   0.034  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.567   0.584   0.197  1.00  0.00           C  
HETATM   19  O3  UNL     1      -5.707   0.481  -0.326  1.00  0.00           O  
HETATM   20  O4  UNL     1      -4.211   1.718   0.895  1.00  0.00           O  
HETATM   21  H1  UNL     1       3.267  -1.971   0.717  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.343  -0.820   1.382  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.591   1.212   1.415  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.780   2.749  -0.331  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.743   1.602  -0.968  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.111   1.019  -2.430  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.481   1.426  -2.244  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.050  -1.861   1.635  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.113  -2.658   0.347  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.794  -0.124   1.934  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.716  -1.728   1.866  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.099  -1.405  -0.483  1.00  0.00           H  
HETATM   33  H13 UNL     1      -4.687   2.601   0.729  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4    4    9
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7    8
CONECT    7   23
CONECT    8    9    9   24
CONECT    9   25
CONECT   10   11   11   14
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14   17
CONECT   14   15
CONECT   15   16   28   29
CONECT   16   17   30   31
CONECT   17   18   32
CONECT   18   19   19   20
CONECT   20   33
END

HMDB0060647
     RDKit          3D
4-hydroxy ketorolac
 33 35  0  0  0  0  0  0  0  0999 V2000
    1.2776   -2.2863   -0.5883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1380   -1.0041   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3332   -0.2736   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3787   -0.9303    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5378   -0.2958    0.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795    1.0410    0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8508    1.6831    0.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835    1.7073   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    1.0498   -0.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1797   -0.4655   -0.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321    0.4965   -1.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9062    0.7242   -1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -0.1253   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444   -0.8186   -0.2030 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7935   -1.7403    0.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576   -1.0323    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6333   -0.5546    0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670    0.5836    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7066    0.4811   -0.3261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113    1.7179    0.8947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2673   -1.9706    0.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3430   -0.8201    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5909    1.2122    1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7796    2.7487   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428    1.6022   -0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110    1.0191   -2.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808    1.4257   -2.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0501   -1.8609    1.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128   -2.6583    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.1239    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7160   -1.7280    1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993   -1.4051   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6869    2.6014    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9  3  1  0
 14 10  1  0
 17 13  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxyketorolac	HMDB

Chemical Formula

C₁₅H₁₃NO₄

Average Molecular Weight

271.268

Monoisotopic Molecular Weight

271.084457909

IUPAC Name

5-(4-hydroxybenzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

Traditional Name

5-(4-hydroxybenzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H13NO4/c17-10-3-1-9(2-4-10)14(18)13-6-5-12-11(15(19)20)7-8-16(12)13/h1-6,11,17H,7-8H2,(H,19,20)

InChI Key

PIQMOWBWPFGZMW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
Benzoyl
Pyrrolizine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060647)

Organ

Kidney (HMDB: HMDB0060647)
Liver (HMDB: HMDB0060647)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060647)

Cellular substructure

Cytoplasm (HMDB: HMDB0060647)

Source

Endogenous

Endogenous (HMDB: HMDB0060647)

Process

Not Available

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	0.9 g/L	ALOGPS
logP	2.44	ALOGPS
logP	1.98	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.18 m³·mol⁻¹	ChemAxon
Polarizability	27.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.83	31661259
DarkChem	[M-H]-	159.625	31661259
DeepCCS	[M+H]+	160.489	30932474
DeepCCS	[M-H]-	158.093	30932474
DeepCCS	[M-2H]-	190.977	30932474
DeepCCS	[M+Na]+	166.482	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	166.6	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	165.5	32859911
AllCCS	[M+Na-2H]-	165.0	32859911
AllCCS	[M+HCOO]-	164.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-hydroxy ketorolac	OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=C(O)C=C1	3903.2	Standard polar	33892256
4-hydroxy ketorolac	OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=C(O)C=C1	2481.8	Standard non polar	33892256
4-hydroxy ketorolac	OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=C(O)C=C1	2816.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-hydroxy ketorolac,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1CCN2C(C(=O)C3=CC=C(O)C=C3)=CC=C12	2730.7	Semi standard non polar	33892256
4-hydroxy ketorolac,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C(=O)C2=CC=C3C(C(=O)O)CCN23)C=C1	2742.4	Semi standard non polar	33892256
4-hydroxy ketorolac,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1CCN2C(C(=O)C3=CC=C(O[Si](C)(C)C)C=C3)=CC=C12	2730.2	Semi standard non polar	33892256
4-hydroxy ketorolac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CCN2C(C(=O)C3=CC=C(O)C=C3)=CC=C12	2999.8	Semi standard non polar	33892256
4-hydroxy ketorolac,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)C2=CC=C3C(C(=O)O)CCN23)C=C1	3008.8	Semi standard non polar	33892256
4-hydroxy ketorolac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CCN2C(C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=CC=C12	3226.1	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 - 4-hydroxy ketorolac GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1940000000-8ebb71ecaf4761d10dc5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-hydroxy ketorolac GC-MS (2 TMS) - 70eV, Positive	splash10-0006-6943100000-670c828bac7c268337ff	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-hydroxy ketorolac 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 - 4-hydroxy ketorolac 10V, Positive-QTOF	splash10-0fk9-0090000000-7cbdfe138a74e1e6ec47	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 20V, Positive-QTOF	splash10-0fk9-1980000000-22071239caac841df86e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 40V, Positive-QTOF	splash10-0aec-4900000000-13a5e11f12f167606ae3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 10V, Negative-QTOF	splash10-00b9-0090000000-65e478c08ad9f752c153	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 20V, Negative-QTOF	splash10-004i-0190000000-527081ffd133e6ff3807	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 40V, Negative-QTOF	splash10-0kcu-4940000000-5de6c2d588fa15369190	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 10V, Positive-QTOF	splash10-00di-0090000000-41deed6d599254c8050f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 20V, Positive-QTOF	splash10-0udi-0290000000-b4a41dced66d06272963	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 40V, Positive-QTOF	splash10-00e9-1960000000-22c4a5da0bc1bee14021	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 10V, Negative-QTOF	splash10-00fr-0090000000-1adc776225e8319beceb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 20V, Negative-QTOF	splash10-004i-0490000000-5e3af8cc7f689e06a220	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy ketorolac 40V, Negative-QTOF	splash10-0f6x-6950000000-fb296fa23a83cc5275cc	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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
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

3082630

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

Showing metabocard for 4-hydroxy ketorolac (HMDB0060647)

MOL for HMDB0060647 (4-hydroxy ketorolac)

3D MOL for HMDB0060647 (4-hydroxy ketorolac)

3D SDF for HMDB0060647 (4-hydroxy ketorolac)

3D-SDF for HMDB0060647 (4-hydroxy ketorolac)

PDB for HMDB0060647 (4-hydroxy ketorolac)

3D PDB for HMDB0060647 (4-hydroxy ketorolac)

SMILES for HMDB0060647 (4-hydroxy ketorolac)

INCHI for HMDB0060647 (4-hydroxy ketorolac)

Structure for HMDB0060647 (4-hydroxy ketorolac)

3D Structure for HMDB0060647 (4-hydroxy ketorolac)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra