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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015471

Secondary Accession Numbers

HMDB15471

Metabolite Identification

Common Name

Salsalate

Description

Salsalate is a nonsteroidal anti-inflammatory agent for oral administration. Salsalate's mode of action as an anti-inflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. The usefulness of salicylic acid, the active in vivo product of salsalate, in the treatment of arthritic disorders has been established. In contrast to aspirin, salsalate causes no greater fecal gastrointestinal blood loss than placebo. Salsalate is readily soluble in the small intestine where it is partially hydrolyzed to two molecules of salicylic acid. A significant portion of the parent compound is absorbed unchanged and undergoes rapid esterase hydrolysis in the body. The parent compound has an elimination half-life of about 1 hour. Salicylic acid (the active metabolite) biotransformation is saturated at anti-inflammatory doses of salsalate. Such capacity limited biotransformation results in an increase in the half-life of salicylic acid from 3.5 to 16 or more hours.

Structure

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

HMDB0015471
     RDKit          3D
Salsalate
 29 30  0  0  0  0  0  0  0  0999 V2000
    0.0889   -1.6983    0.5402 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5558   -0.6040    0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3314    0.1664   -0.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634   -0.1661   -0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -0.8990   -1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4796   -1.1992   -2.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953   -0.7684   -1.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9395   -0.0375   -0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5831    0.2605    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1196    1.0373    1.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793    1.4282    2.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7964    1.3622    1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9317   -0.2394    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7865   -1.0910    0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065   -0.8230    1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6224    0.3591    0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.2217   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4683    0.9165   -0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7895    1.8689   -0.9433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3927   -1.2330   -2.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8133   -1.7668   -2.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4341   -1.0274   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6455    0.3063    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4540    1.5265    2.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623   -2.0076    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7759   -1.4627    1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6863    0.5806    0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2766    2.1274   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    1.8619   -1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  9  4  1  0
 18 13  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
 12 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  1  0
 19 29  1  0
M  END

1399
  Mrv0541 02231215282D          

 19 20  0  0  0  0            999 V2000
    4.5079   -0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.2870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 11  1  0  0  0  0
  2  9  1  0  0  0  0
  3 11  2  0  0  0  0
  4 19  1  0  0  0  0
  5 19  2  0  0  0  0
  6  8  1  0  0  0  0
  6 10  2  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  2  0  0  0  0
  8 12  2  0  0  0  0
  8 19  1  0  0  0  0
  9 16  2  0  0  0  0
 10 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  2  0  0  0  0
 16 18  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015471

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O5/c15-11-7-3-1-5-9(11)14(18)19-12-8-4-2-6-10(12)13(16)17/h1-8,15H,(H,16,17)

> <INCHI_KEY>
WVYADZUPLLSGPU-UHFFFAOYSA-N

> <FORMULA>
C14H10O5

> <MOLECULAR_WEIGHT>
258.2262

> <EXACT_MASS>
258.05282343

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.92421627298441

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-hydroxybenzoyloxy)benzoic acid

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.6386988149999993

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.668257147887239

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4033106020174717

> <JCHEM_PKA_STRONGEST_BASIC>
-4.291296693421992

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
67.09800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salina

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015471
     RDKit          3D
Salsalate
 29 30  0  0  0  0  0  0  0  0999 V2000
    0.0889   -1.6983    0.5402 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5558   -0.6040    0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3314    0.1664   -0.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634   -0.1661   -0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -0.8990   -1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4796   -1.1992   -2.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953   -0.7684   -1.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9395   -0.0375   -0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5831    0.2605    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1196    1.0373    1.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793    1.4282    2.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7964    1.3622    1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9317   -0.2394    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7865   -1.0910    0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065   -0.8230    1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6224    0.3591    0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.2217   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4683    0.9165   -0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7895    1.8689   -0.9433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3927   -1.2330   -2.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8133   -1.7668   -2.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4341   -1.0274   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6455    0.3063    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4540    1.5265    2.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623   -2.0076    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7759   -1.4627    1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6863    0.5806    0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2766    2.1274   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    1.8619   -1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  9  4  1  0
 18 13  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
 12 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  1  0
 19 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1399                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415  -0.092   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081   2.218   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081  -2.402   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.416   2.218   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.748   2.218   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.748  -0.862   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747  -0.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082  -0.092   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747   1.448   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -2.402   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -0.862   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.416  -0.862   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -0.862   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082  -3.172   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.416  -2.402   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   2.218   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -0.092   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080   1.448   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082   1.448   0.000  0.00  0.00           C+0
CONECT    1    6   11                                                       
CONECT    2    9                                                            
CONECT    3   11                                                            
CONECT    4   19                                                            
CONECT    5   19                                                            
CONECT    6    1    8   10                                                  
CONECT    7    9   11   13                                                  
CONECT    8    6   12   19                                                  
CONECT    9    2    7   16                                                  
CONECT   10    6   14                                                       
CONECT   11    1    3    7                                                  
CONECT   12    8   15                                                       
CONECT   13    7   17                                                       
CONECT   14   10   15                                                       
CONECT   15   12   14                                                       
CONECT   16    9   18                                                       
CONECT   17   13   18                                                       
CONECT   18   16   17                                                       
CONECT   19    4    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0015471
HETATM    1  O1  UNL     1       0.089  -1.698   0.540  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.556  -0.604   0.070  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.331   0.166  -0.609  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.663  -0.166  -0.805  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.119  -0.899  -1.881  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.480  -1.199  -2.017  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.395  -0.768  -1.077  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.940  -0.037  -0.005  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.583   0.260   0.128  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.120   1.037   1.271  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.979   1.428   2.132  1.00  0.00           O  
HETATM   12  O4  UNL     1      -0.796   1.362   1.454  1.00  0.00           O  
HETATM   13  C9  UNL     1       1.932  -0.239   0.261  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.786  -1.091   0.974  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.106  -0.823   1.203  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.622   0.359   0.698  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.832   1.222  -0.004  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.468   0.917  -0.224  1.00  0.00           C  
HETATM   19  O5  UNL     1       1.789   1.869  -0.943  1.00  0.00           O  
HETATM   20  H1  UNL     1      -1.393  -1.233  -2.613  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.813  -1.767  -2.855  1.00  0.00           H  
HETATM   22  H3  UNL     1      -5.434  -1.027  -1.230  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.645   0.306   0.738  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.454   1.526   2.388  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.362  -2.008   1.359  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.776  -1.463   1.747  1.00  0.00           H  
HETATM   27  H8  UNL     1       5.686   0.581   0.879  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.277   2.127  -0.377  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.864   1.862  -1.204  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4
CONECT    4    5    5    9
CONECT    5    6   20
CONECT    6    7    7   21
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   24
CONECT   13   14   14   18
CONECT   14   15   25
CONECT   15   16   16   26
CONECT   16   17   27
CONECT   17   18   18   28
CONECT   18   19
CONECT   19   29
END

HMDB0015471
     RDKit          3D
Salsalate
 29 30  0  0  0  0  0  0  0  0999 V2000
    0.0889   -1.6983    0.5402 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5558   -0.6040    0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3314    0.1664   -0.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634   -0.1661   -0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -0.8990   -1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4796   -1.1992   -2.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953   -0.7684   -1.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9395   -0.0375   -0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5831    0.2605    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1196    1.0373    1.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793    1.4282    2.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7964    1.3622    1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9317   -0.2394    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7865   -1.0910    0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065   -0.8230    1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6224    0.3591    0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.2217   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4683    0.9165   -0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7895    1.8689   -0.9433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3927   -1.2330   -2.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8133   -1.7668   -2.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4341   -1.0274   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6455    0.3063    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4540    1.5265    2.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623   -2.0076    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7759   -1.4627    1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6863    0.5806    0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2766    2.1274   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    1.8619   -1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  9  4  1  0
 18 13  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
 12 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 17 28  1  0
 19 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Carboxyphenyl salicylate	ChEBI
Disalcid	ChEBI
Disalicylic acid	ChEBI
Disalicylsaeure	ChEBI
O-Salicylcylsalicylsaeure	ChEBI
O-Salicylsalicylic acid	ChEBI
Salicylic acid bimolecular ester	ChEBI
Salicyloxysalicylic acid	ChEBI
Salicyloylsalicylic acid	ChEBI
Salicylsalicylic acid	ChEBI
Salsalato	ChEBI
Salsalatum	ChEBI
Sasapyrin	ChEBI
Sasapyrine	ChEBI
Sasapyrinum	ChEBI
2-Carboxyphenyl salicylic acid	Generator
Disalicylate	Generator
O-Salicylsalicylate	Generator
Salicylate bimolecular ester	Generator
Salicyloxysalicylate	Generator
Salicyloylsalicylate	Generator
Salicylsalicylate	Generator
Salsalic acid	Generator
Salflex	HMDB
Salsitab	HMDB
Saloxium	HMDB
Arcylate	HMDB
Argesic	HMDB
Upsher-smith brand OF salicylsalicylic acid	HMDB
mono-Gesic	HMDB
Salicyl salicylate	HMDB
Benzoic acid, 2-hydroxy-, 2-carboxyphenyl ester	HMDB

Chemical Formula

C₁₄H₁₀O₅

Average Molecular Weight

258.2262

Monoisotopic Molecular Weight

258.05282343

IUPAC Name

2-(2-hydroxybenzoyloxy)benzoic acid

Traditional Name

salina

CAS Registry Number

552-94-3

SMILES

OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C14H10O5/c15-11-7-3-1-5-9(11)14(18)19-12-8-4-2-6-10(12)13(16)17/h1-8,15H,(H,16,17)

InChI Key

WVYADZUPLLSGPU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
O-hydroxybenzoic acid ester
Benzoate ester
Salicylic acid or derivatives
Phenol ester
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous acid
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:9014 )
salicylates (CHEBI:9014 )
benzoate ester (CHEBI:9014 )
benzoic acids (CHEBI:9014 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015471)
Membrane (HMDB: HMDB0015471)

Source

Exogenous

Exogenous (HMDB: HMDB0015471)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Salsalate Action Pathway (PathBank: SMP0000707)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	147 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.25 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	151.271	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001385

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.64	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.1 m³·mol⁻¹	ChemAxon
Polarizability	24.92 Å³	ChemAxon
Number of Rings	2	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]+	156.681	31661259
DarkChem	[M-H]-	157.202	31661259
DeepCCS	[M+H]+	154.724	30932474
DeepCCS	[M-H]-	152.329	30932474
DeepCCS	[M-2H]-	185.83	30932474
DeepCCS	[M+Na]+	160.766	30932474
AllCCS	[M+H]+	157.1	32859911
AllCCS	[M+H-H2O]+	153.4	32859911
AllCCS	[M+NH4]+	160.7	32859911
AllCCS	[M+Na]+	161.7	32859911
AllCCS	[M-H]-	156.6	32859911
AllCCS	[M+Na-2H]-	156.0	32859911
AllCCS	[M+HCOO]-	155.6	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.	7.32 minutes	32390414
Predicted by Siyang on May 30, 2022	13.079 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.5 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2169.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	383.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	218.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	303.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	570.4 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	651.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1130.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	454.6 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	1352.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	431.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	431.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	224.2 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	110.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Salsalate	OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O	3399.1	Standard polar	33892256
Salsalate	OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O	2229.7	Standard non polar	33892256
Salsalate	OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O	2240.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Salsalate,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O	2215.3	Semi standard non polar	33892256
Salsalate,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1C(=O)O	2322.6	Semi standard non polar	33892256
Salsalate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O[Si](C)(C)C	2336.6	Semi standard non polar	33892256
Salsalate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O	2463.0	Semi standard non polar	33892256
Salsalate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1C(=O)O	2582.9	Semi standard non polar	33892256
Salsalate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	2783.7	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 - Salsalate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0900000000-08ef63493442bd429803	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salsalate GC-MS (2 TMS) - 70eV, Positive	splash10-0006-1902000000-a534dd5fbce0addc2689	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Salsalate 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 - Salsalate 10V, Positive-QTOF	splash10-0a4l-0290000000-f4cf330edbdce3dcb9d9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 20V, Positive-QTOF	splash10-00dl-2790000000-d10c0ecafec2d5a9b8da	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 40V, Positive-QTOF	splash10-0uk9-9500000000-1c6bcbed20e1fdde65d5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 10V, Negative-QTOF	splash10-0bt9-0090000000-18be47c801d297da7fd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 20V, Negative-QTOF	splash10-03di-2190000000-e79b3cc4f48105579dfa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 40V, Negative-QTOF	splash10-0006-9300000000-4b93814ccff2c3ff93c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 10V, Positive-QTOF	splash10-00di-2900000000-4731b64bd7f33c92a35f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 20V, Positive-QTOF	splash10-00di-4900000000-dccaf7be8cfaf84a3394	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 40V, Positive-QTOF	splash10-0f6x-9100000000-5cf64c11c5e0756d69ba	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 10V, Negative-QTOF	splash10-052f-9150000000-cdfb845a922b2d914e6f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 20V, Negative-QTOF	splash10-0006-9000000000-eb933123d7cea37777a2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Salsalate 40V, Negative-QTOF	splash10-0006-9300000000-8ba532e581907de890bd	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Salsalate Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01399	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01399	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01399

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4977

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Salsalate

METLIN ID

Not Available

PubChem Compound

5161

PDB ID

Not Available

ChEBI ID

9014

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. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Stichtenoth DO, Zeidler H, Frolich JC: [New non-steroidal anti-rheumatic drugs: selective inhibitors of inducible cyclooxygenase]. Med Klin (Munich). 1998 Jul 15;93(7):407-15. [PubMed:9711054 ]
Schaefer MG, Plowman BK, Morreale AP, Egan M: Interaction of rofecoxib and celecoxib with warfarin. Am J Health Syst Pharm. 2003 Jul 1;60(13):1319-23. [PubMed:12901032 ]
Motsko SP, Rascati KL, Busti AJ, Wilson JP, Barner JC, Lawson KA, Worchel J: Temporal relationship between use of NSAIDs, including selective COX-2 inhibitors, and cardiovascular risk. Drug Saf. 2006;29(7):621-32. [PubMed:16808554 ]
Josephs MD, Cheng G, Ksontini R, Moldawer LL, Hocking MP: Products of cyclooxygenase-2 catalysis regulate postoperative bowel motility. J Surg Res. 1999 Sep;86(1):50-4. [PubMed:10452868 ]

Enzyme Details

2. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Stevenson DD: Aspirin and NSAID sensitivity. Immunol Allergy Clin North Am. 2004 Aug;24(3):491-505, vii. [PubMed:15242723 ]
Schmidt A, Hescheler J, Offermanns S, Spicher K, Hinsch KD, Klinz FJ, Codina J, Birnbaumer L, Gausepohl H, Frank R, et al.: Involvement of pertussis toxin-sensitive G-proteins in the hormonal inhibition of dihydropyridine-sensitive Ca2+ currents in an insulin-secreting cell line (RINm5F). J Biol Chem. 1991 Sep 25;266(27):18025-33. [PubMed:1680855 ]
Josephs MD, Cheng G, Ksontini R, Moldawer LL, Hocking MP: Products of cyclooxygenase-2 catalysis regulate postoperative bowel motility. J Surg Res. 1999 Sep;86(1):50-4. [PubMed:10452868 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Salsalate (HMDB0015471)

MOL for HMDB0015471 (Salsalate)

3D MOL for HMDB0015471 (Salsalate)

3D SDF for HMDB0015471 (Salsalate)

3D-SDF for HMDB0015471 (Salsalate)

PDB for HMDB0015471 (Salsalate)

3D PDB for HMDB0015471 (Salsalate)

SMILES for HMDB0015471 (Salsalate)

INCHI for HMDB0015471 (Salsalate)

Structure for HMDB0015471 (Salsalate)

3D Structure for HMDB0015471 (Salsalate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References