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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015160

Secondary Accession Numbers

HMDB15160

Metabolite Identification

Common Name

Amlexanox

Description

Amlexanox, also known as aphthasol or solfa, belongs to the class of organic compounds known as chromeno[2,3-b]pyridine-5-ones. Chromeno[2,3-b]pyridine-5-ones are compounds containing a Chromeno[2,3-b]pyridine moiety that carries an oxo group at the 5-position. Amlexanox is a drug which is used as a paste in the mouth to treat aphthous ulcers (canker sores). . Amlexanox is an extremely weak basic (essentially neutral) compound (based on its pKa). A pyridochromene-derived monocarboxylic acid having an amino substituent at the 2-position, an oxo substituent at the 5-position and an isopropyl substituent at the 7-position.

Structure

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

HMDB0015160
     RDKit          3D
Amlexanox
 36 38  0  0  0  0  0  0  0  0999 V2000
    4.9717   -0.7915   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1947    0.4494   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418    1.2215    0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8807    0.0491    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7582   -0.7520    1.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -1.1298    1.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122   -0.6759    1.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893   -0.9983    1.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8937   -0.6079    0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1137   -0.9720    1.3603 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2498   -0.5874    0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5096   -0.9885    1.2839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378    0.2132   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4792    0.6219   -1.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431    1.3334   -2.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6856    0.2234   -0.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0136    0.5948   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717    0.1808   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113    0.5581   -0.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5686    1.2692   -1.7447 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    0.1110   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431    0.4685   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7366   -0.4486   -1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291   -1.4931   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4008   -1.3125    0.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0536    1.0725   -1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7341    0.6361    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2378    1.5746    1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3722    2.1544    0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6795   -1.0773    1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300   -1.7501    2.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8619   -0.6175    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1058   -1.6609    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2385    0.8252    0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    1.2189   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8081    1.0871   -1.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22  4  1  0
 21  7  1  0
 18  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
 12 32  1  0
 12 33  1  0
 16 34  1  0
 17 35  1  0
 22 36  1  0
M  END

1025
  Mrv0541 02231215112D          

 22 24  0  0  0  0            999 V2000
    5.2784   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784    1.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875    1.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9067    0.1497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7303   -1.1391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1907   -1.1304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660    0.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5639    0.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8264    0.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5639   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9928    0.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2784    0.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3692    1.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8264   -1.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9928   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7303    0.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4778    0.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4778   -0.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1907    0.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 18  1  0  0  0  0
  2 14  2  0  0  0  0
  3 22  1  0  0  0  0
  4 22  2  0  0  0  0
  5 18  2  0  0  0  0
  5 21  1  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 16  1  0  0  0  0
  8 10  2  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9 14  1  0  0  0  0
 11 17  1  0  0  0  0
 12 17  2  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 13 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015160

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14N2O4/c1-7(2)8-3-4-12-9(5-8)13(19)10-6-11(16(20)21)14(17)18-15(10)22-12/h3-7H,1-2H3,(H2,17,18)(H,20,21)

> <INCHI_KEY>
SGRYPYWGNKJSDL-UHFFFAOYSA-N

> <FORMULA>
C16H14N2O4

> <MOLECULAR_WEIGHT>
298.2934

> <EXACT_MASS>
298.095356946

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.82499978886283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
3.6545489580000003

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.303939649642112

> <JCHEM_PKA_STRONGEST_BASIC>
0.874259879101479

> <JCHEM_POLAR_SURFACE_AREA>
102.51

> <JCHEM_REFRACTIVITY>
81.4338

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aphthasol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015160
     RDKit          3D
Amlexanox
 36 38  0  0  0  0  0  0  0  0999 V2000
    4.9717   -0.7915   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1947    0.4494   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418    1.2215    0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8807    0.0491    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7582   -0.7520    1.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -1.1298    1.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122   -0.6759    1.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893   -0.9983    1.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8937   -0.6079    0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1137   -0.9720    1.3603 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2498   -0.5874    0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5096   -0.9885    1.2839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378    0.2132   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4792    0.6219   -1.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431    1.3334   -2.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6856    0.2234   -0.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0136    0.5948   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717    0.1808   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113    0.5581   -0.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5686    1.2692   -1.7447 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    0.1110   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431    0.4685   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7366   -0.4486   -1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291   -1.4931   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4008   -1.3125    0.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0536    1.0725   -1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7341    0.6361    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2378    1.5746    1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3722    2.1544    0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6795   -1.0773    1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300   -1.7501    2.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8619   -0.6175    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1058   -1.6609    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2385    0.8252    0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    1.2189   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8081    1.0871   -1.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22  4  1  0
 21  7  1  0
 18  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
 12 32  1  0
 12 33  1  0
 16 34  1  0
 17 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1025                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.853  -2.073   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.853   2.547   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      15.283   2.584   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.626   0.279   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      12.563  -2.126   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      15.289  -2.110   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.417   1.044   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747   0.269   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.519   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.143   1.060   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.519  -1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747  -1.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.187   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.853   1.007   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   0.279   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.423   2.584   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.143  -2.126   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.187  -1.303   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.563   1.060   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.959   0.269   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.959  -1.335   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.289   1.044   0.000  0.00  0.00           C+0
CONECT    1   11   18                                                       
CONECT    2   14                                                            
CONECT    3   22                                                            
CONECT    4   22                                                            
CONECT    5   18   21                                                       
CONECT    6   21                                                            
CONECT    7    8   15   16                                                  
CONECT    8    7   10   12                                                  
CONECT    9   10   11   14                                                  
CONECT   10    8    9                                                       
CONECT   11    1    9   17                                                  
CONECT   12    8   17                                                       
CONECT   13   14   18   19                                                  
CONECT   14    2    9   13                                                  
CONECT   15    7                                                            
CONECT   16    7                                                            
CONECT   17   11   12                                                       
CONECT   18    1    5   13                                                  
CONECT   19   13   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21    5    6   20                                                  
CONECT   22    3    4   20                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0015160
HETATM    1  C1  UNL     1       4.972  -0.791  -0.799  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.195   0.449  -0.371  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.942   1.221   0.696  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.881   0.049   0.148  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.758  -0.752   1.290  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.527  -1.130   1.780  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.412  -0.676   1.083  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.789  -0.998   1.495  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.894  -0.608   0.890  1.00  0.00           C  
HETATM   10  N1  UNL     1      -3.114  -0.972   1.360  1.00  0.00           N  
HETATM   11  C9  UNL     1      -4.250  -0.587   0.762  1.00  0.00           C  
HETATM   12  N2  UNL     1      -5.510  -0.988   1.284  1.00  0.00           N  
HETATM   13  C10 UNL     1      -4.238   0.213  -0.385  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.479   0.622  -1.022  1.00  0.00           C  
HETATM   15  O2  UNL     1      -5.443   1.333  -2.040  1.00  0.00           O  
HETATM   16  O3  UNL     1      -6.686   0.223  -0.502  1.00  0.00           O  
HETATM   17  C12 UNL     1      -3.014   0.595  -0.881  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.872   0.181  -0.240  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.611   0.558  -0.728  1.00  0.00           C  
HETATM   20  O4  UNL     1      -0.569   1.269  -1.745  1.00  0.00           O  
HETATM   21  C15 UNL     1       0.494   0.111  -0.041  1.00  0.00           C  
HETATM   22  C16 UNL     1       1.743   0.469  -0.501  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.737  -0.449  -1.512  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.229  -1.493  -1.262  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.401  -1.312   0.086  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.054   1.072  -1.270  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.734   0.636   1.180  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.238   1.575   1.479  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.372   2.154   0.242  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.679  -1.077   1.795  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.430  -1.750   2.665  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.862  -0.618   2.206  1.00  0.00           H  
HETATM   33  H11 UNL     1      -6.106  -1.661   0.756  1.00  0.00           H  
HETATM   34  H12 UNL     1      -7.239   0.825   0.093  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.932   1.219  -1.771  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.808   1.087  -1.384  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4   26
CONECT    3   27   28   29
CONECT    4    5    5   22
CONECT    5    6   30
CONECT    6    7    7   31
CONECT    7    8   21
CONECT    8    9
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   12   13   13
CONECT   12   32   33
CONECT   13   14   17
CONECT   14   15   15   16
CONECT   16   34
CONECT   17   18   18   35
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   22
CONECT   22   36
END

HMDB0015160
     RDKit          3D
Amlexanox
 36 38  0  0  0  0  0  0  0  0999 V2000
    4.9717   -0.7915   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1947    0.4494   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418    1.2215    0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8807    0.0491    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7582   -0.7520    1.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -1.1298    1.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122   -0.6759    1.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893   -0.9983    1.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8937   -0.6079    0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1137   -0.9720    1.3603 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2498   -0.5874    0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5096   -0.9885    1.2839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378    0.2132   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4792    0.6219   -1.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431    1.3334   -2.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6856    0.2234   -0.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0136    0.5948   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717    0.1808   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113    0.5581   -0.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5686    1.2692   -1.7447 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    0.1110   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431    0.4685   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7366   -0.4486   -1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291   -1.4931   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4008   -1.3125    0.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0536    1.0725   -1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7341    0.6361    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2378    1.5746    1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3722    2.1544    0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6795   -1.0773    1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300   -1.7501    2.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8619   -0.6175    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1058   -1.6609    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2385    0.8252    0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    1.2189   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8081    1.0871   -1.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22  4  1  0
 21  7  1  0
 18  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
 12 32  1  0
 12 33  1  0
 16 34  1  0
 17 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylic acid	ChEBI
Amlexanoxo	ChEBI
Amlexanoxum	ChEBI
Aphthasol	Kegg
Solfa	Kegg
2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylate	Generator
2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3b)pyridine-3-carboxylic acid	HMDB
GlaxoSmithKline brand OF amlexanox	HMDB
Amoxanox	HMDB

Chemical Formula

C₁₆H₁₄N₂O₄

Average Molecular Weight

298.2934

Monoisotopic Molecular Weight

298.095356946

IUPAC Name

2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid

Traditional Name

aphthasol

CAS Registry Number

68302-57-8

SMILES

CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1

InChI Identifier

InChI=1S/C16H14N2O4/c1-7(2)8-3-4-12-9(5-8)13(19)10-6-11(16(20)21)14(17)18-15(10)22-12/h3-7H,1-2H3,(H2,17,18)(H,20,21)

InChI Key

SGRYPYWGNKJSDL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromeno[2,3-b]pyridine-5-ones. Chromeno[2,3-b]pyridine-5-ones are compounds containing a Chromeno[2,3-b]pyridine moiety that carries an oxo group at the 5-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromeno[2,3-b]pyridine-5-ones

Alternative Parents

Substituents

Chromeno[2,3-b]pyridine-5-one
Chromenopyridine
Pyranopyridine
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Aminopyridine
Pyranone
Pyran
Pyridine
Benzenoid
Imidolactam
Heteroaromatic compound
Vinylogous amide
Amino acid or derivatives
Amino acid
Oxacycle
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Organooxygen compound
Organonitrogen compound
Primary amine
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:31205 )
pyridochromene (CHEBI:31205 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015160)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.15 g/L	Not Available
LogP	4.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.76	ALOGPS
logP	3.65	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	0.87	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.51 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.43 m³·mol⁻¹	ChemAxon
Polarizability	30.82 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]+	171.215	31661259
DarkChem	[M-H]-	170.909	31661259
DeepCCS	[M+H]+	178.239	30932474
DeepCCS	[M-H]-	175.857	30932474
DeepCCS	[M-2H]-	210.044	30932474
DeepCCS	[M+Na]+	186.214	30932474
AllCCS	[M+H]+	168.0	32859911
AllCCS	[M+H-H2O]+	164.4	32859911
AllCCS	[M+NH4]+	171.3	32859911
AllCCS	[M+Na]+	172.2	32859911
AllCCS	[M-H]-	172.4	32859911
AllCCS	[M+Na-2H]-	172.0	32859911
AllCCS	[M+HCOO]-	171.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amlexanox	CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1	3973.8	Standard polar	33892256
Amlexanox	CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1	2634.1	Standard non polar	33892256
Amlexanox	CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1	3085.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amlexanox,1TMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1	3090.6	Semi standard non polar	33892256
Amlexanox,1TMS,isomer #2	CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1	3064.7	Semi standard non polar	33892256
Amlexanox,2TMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1	3012.0	Semi standard non polar	33892256
Amlexanox,2TMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1	2992.9	Standard non polar	33892256
Amlexanox,2TMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1	3628.1	Standard polar	33892256
Amlexanox,2TMS,isomer #2	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1	2916.1	Semi standard non polar	33892256
Amlexanox,2TMS,isomer #2	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1	3016.7	Standard non polar	33892256
Amlexanox,2TMS,isomer #2	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1	3566.6	Standard polar	33892256
Amlexanox,3TMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1	2916.0	Semi standard non polar	33892256
Amlexanox,3TMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1	3023.0	Standard non polar	33892256
Amlexanox,3TMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C=C3C(=O)C2=C1	3348.7	Standard polar	33892256
Amlexanox,1TBDMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3296.3	Semi standard non polar	33892256
Amlexanox,1TBDMS,isomer #2	CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C(C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1	3290.3	Semi standard non polar	33892256
Amlexanox,2TBDMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3375.1	Semi standard non polar	33892256
Amlexanox,2TBDMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3323.5	Standard non polar	33892256
Amlexanox,2TBDMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3738.0	Standard polar	33892256
Amlexanox,2TBDMS,isomer #2	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1	3316.4	Semi standard non polar	33892256
Amlexanox,2TBDMS,isomer #2	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1	3392.4	Standard non polar	33892256
Amlexanox,2TBDMS,isomer #2	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O)C=C3C(=O)C2=C1	3648.5	Standard polar	33892256
Amlexanox,3TBDMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3479.4	Semi standard non polar	33892256
Amlexanox,3TBDMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3541.8	Standard non polar	33892256
Amlexanox,3TBDMS,isomer #1	CC(C)C1=CC=C2OC3=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3583.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amlexanox GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0390000000-7ee61efa9635374d2e64	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amlexanox GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9456000000-b9624d4096b63a87688a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amlexanox GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amlexanox 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amlexanox , positive-QTOF	splash10-0002-0091000000-00993cade43b41e35544	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amlexanox 35V, Negative-QTOF	splash10-0udi-0090000000-b3b8517df7b9224b9b0f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amlexanox 35V, Positive-QTOF	splash10-000t-0090000000-8e4fc4d5f71fd828eec7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 10V, Positive-QTOF	splash10-0002-0090000000-6251cf97e8c45ca915cd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 20V, Positive-QTOF	splash10-0zgi-0090000000-4e3a6005c4c7903e8304	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 40V, Positive-QTOF	splash10-000i-2290000000-4ce7d5b38aec871db123	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 10V, Negative-QTOF	splash10-0udj-0090000000-363c3c4f6b29bd793e36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 20V, Negative-QTOF	splash10-0udi-0090000000-4242451c12a02c097cfc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 40V, Negative-QTOF	splash10-0ktr-2290000000-fe4c8daf1591c12dffa9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 10V, Positive-QTOF	splash10-0002-0090000000-298901b9b72f633ddf1a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 20V, Positive-QTOF	splash10-001j-0090000000-7ae2b8d3206733616bb9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 40V, Positive-QTOF	splash10-0udi-0290000000-23dd9de629c968ef59aa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 10V, Negative-QTOF	splash10-0udi-0090000000-977fc6f1952ba1618211	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 20V, Negative-QTOF	splash10-0udi-0090000000-d126c3ae8460a1113700	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlexanox 40V, Negative-QTOF	splash10-01p9-0590000000-299584979cf6ca2fac81	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB01025	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01025	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01025

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2076

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amlexanox

METLIN ID

Not Available

PubChem Compound

2161

PDB ID

ANW

ChEBI ID

31205

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

Bell J: Amlexanox for the treatment of recurrent aphthous ulcers. Clin Drug Investig. 2005;25(9):555-66. [PubMed:17532700 ]

Enzymes

Enzyme Details

1. Interleukin-3 precursor

General function:: Not Available
Specific function:: This CSF induces granulocytes, macrophages, mast cells, stem cells, erythroid cells, eosinophils and megakaryocytes
Gene Name:: IL3
Uniprot ID:: P08700
Molecular weight:: 17233.0

References

Urisu A, Iimi K, Kondo Y, Horiba F, Masuda S, Tsuruta M, Yazaki T, Torii S: [Inhibitory action amlexanox on interleukin-3-induced enhancement of histamine releasability of human leukocytes]. Arerugi. 1990 Oct;39(10):1448-54. [PubMed:1701989 ]
Nagai H, Suda H, Iwama T, Daikoku M, Yanagihara Y, Koda A: Effect of NZ-107, a newly synthesized pyridazinone derivative, on antigen-induced contraction of human bronchial strips and histamine release from human lung fragments or leukocytes. Int Arch Allergy Immunol. 1992;98(1):57-63. [PubMed:1378042 ]

Enzyme Details

2. Heparin-binding growth factor 1

General function:: Involved in fibroblast growth factor receptor binding
Specific function:: The heparin-binding growth factors are angiogenic agents in vivo and are potent mitogens for a variety of cell types in vitro. There are differences in the tissue distribution and concentration of these 2 growth factors
Gene Name:: FGF1
Uniprot ID:: P05230
Molecular weight:: 17459.6

References

Rajalingam D, Kumar TK, Soldi R, Graziani I, Prudovsky I, Yu C: Molecular mechanism of inhibition of nonclassical FGF-1 export. Biochemistry. 2005 Nov 29;44(47):15472-9. [PubMed:16300395 ]

Showing metabocard for Amlexanox (HMDB0015160)

MOL for HMDB0015160 (Amlexanox)

3D MOL for HMDB0015160 (Amlexanox)

3D SDF for HMDB0015160 (Amlexanox)

3D-SDF for HMDB0015160 (Amlexanox)

PDB for HMDB0015160 (Amlexanox)

3D PDB for HMDB0015160 (Amlexanox)

SMILES for HMDB0015160 (Amlexanox)

INCHI for HMDB0015160 (Amlexanox)

Structure for HMDB0015160 (Amlexanox)

3D Structure for HMDB0015160 (Amlexanox)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References