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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:59:31 UTC

Update Date

2021-09-26 23:04:36 UTC

HMDB ID

HMDB0252185

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Febuxostat

Description

Febuxostat, also known as feburic or uloric, belongs to the class of organic compounds known as thiazolecarboxylic acids and derivatives. These are heterocyclic compounds containing a thiazole ring which bears a carboxylic acid group (or a derivative thereof). Febuxostat is a drug which is used for the treatment of hyperuricemia in patients with gout. Febuxostat is an extremely weak basic (essentially neutral) compound (based on its pKa). A 1,3-thiazolemonocarboxylic acid that is 4-methyl-1,3-thiazole-5-carboxylic acid which is substituted by a 3-cyano-4-(2-methylpropoxy)phenyl group at position 2. This compound has been identified in human blood as reported by (PMID: 31557052 ). Febuxostat is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Febuxostat is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0252185
     RDKit          3D
Febuxostat
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.8121   -1.4942   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010   -0.6269   -0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5257   -0.7633   -0.5161 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6895    0.0177    0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    0.0391    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249    0.9355    0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693    0.9355    0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5344    0.0298    0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9312    0.0105    0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261    0.8942    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802    0.5801    0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4307   -0.8553    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4952    0.8122   -1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482   -0.8804   -0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -1.8196   -1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894   -2.5844   -2.2246 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5323   -0.8460   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7755    1.0187    1.0391 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2455    0.3480    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6331    0.7074    0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6058    0.1034    0.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8758    1.7309    1.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2606   -0.9371   -1.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3269   -2.3963   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825   -1.8681   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0003    1.6602    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    1.6230    1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5526    0.6777    1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4940    1.9331    0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8314    1.2147    1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4447   -1.2017    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2625   -0.9561    1.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7098   -1.4841    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0970   -0.0351   -1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0179    1.7544   -1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5897    0.8249   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0944   -1.5415   -1.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5778    2.4390    1.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  3  0
 14 17  2  0
  4 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19  2  2  0
 17  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 17 37  1  0
 22 38  1  0
M  END


  Mrv0541 02231217572D          

 22 23  0  0  0  0            999 V2000
    3.1261    1.6146    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756    2.9805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2316    3.8204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    1.6146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    2.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    2.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6910    3.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961    3.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  1 19  1  0  0  0  0
  2  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3 22  1  0  0  0  0
  4 22  2  0  0  0  0
  5 17  2  0  0  0  0
  5 18  1  0  0  0  0
  6 21  3  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 15  1  0  0  0  0
 13 21  1  0  0  0  0
 14 16  2  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252185

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)COC1=C(C=C(C=C1)C1=NC(C)=C(S1)C(O)=O)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C16H16N2O3S/c1-9(2)8-21-13-5-4-11(6-12(13)7-17)15-18-10(3)14(22-15)16(19)20/h4-6,9H,8H2,1-3H3,(H,19,20)

> <INCHI_KEY>
BQSJTQLCZDPROO-UHFFFAOYSA-N

> <FORMULA>
C16H16N2O3S

> <MOLECULAR_WEIGHT>
316.375

> <EXACT_MASS>
316.088163078

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.88019656821729

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
3.520929441333333

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0782740305720346

> <JCHEM_PKA_STRONGEST_BASIC>
0.39479959157958755

> <JCHEM_POLAR_SURFACE_AREA>
83.21000000000001

> <JCHEM_REFRACTIVITY>
93.92880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
febuxostat

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252185
     RDKit          3D
Febuxostat
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.8121   -1.4942   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010   -0.6269   -0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5257   -0.7633   -0.5161 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6895    0.0177    0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    0.0391    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249    0.9355    0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693    0.9355    0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5344    0.0298    0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9312    0.0105    0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261    0.8942    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802    0.5801    0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4307   -0.8553    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4952    0.8122   -1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482   -0.8804   -0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -1.8196   -1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894   -2.5844   -2.2246 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5323   -0.8460   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7755    1.0187    1.0391 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2455    0.3480    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6331    0.7074    0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6058    0.1034    0.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8758    1.7309    1.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2606   -0.9371   -1.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3269   -2.3963   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825   -1.8681   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0003    1.6602    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    1.6230    1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5526    0.6777    1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4940    1.9331    0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8314    1.2147    1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4447   -1.2017    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2625   -0.9561    1.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7098   -1.4841    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0970   -0.0351   -1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0179    1.7544   -1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5897    0.8249   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0944   -1.5415   -1.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5778    2.4390    1.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  3  0
 14 17  2  0
  4 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19  2  2  0
 17  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 17 37  1  0
 22 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       5.835   3.014   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.081  -4.051   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.874   5.564   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.032   7.131   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.327   3.014   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       3.080  -3.281   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.415  -6.361   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -4.821   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748  -7.131   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -7.131   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -2.511   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   0.569   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -1.741   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -1.741   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748  -0.201   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -0.201   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   2.109   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.851   4.479   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.311   4.479   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.757   5.725   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -2.511   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.406   5.725   0.000  0.00  0.00           C+0
CONECT    1   17   19                                                       
CONECT    2    8   11                                                       
CONECT    3   22                                                            
CONECT    4   22                                                            
CONECT    5   17   18                                                       
CONECT    6   21                                                            
CONECT    7    8    9   10                                                  
CONECT    8    2    7                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    2   13   14                                                  
CONECT   12   15   16   17                                                  
CONECT   13   11   15   21                                                  
CONECT   14   11   16                                                       
CONECT   15   12   13                                                       
CONECT   16   12   14                                                       
CONECT   17    1    5   12                                                  
CONECT   18    5   19   20                                                  
CONECT   19    1   18   22                                                  
CONECT   20   18                                                            
CONECT   21    6   13                                                       
CONECT   22    3    4   19                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0252185
HETATM    1  C1  UNL     1       5.812  -1.494  -1.101  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.801  -0.627  -0.369  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.526  -0.763  -0.516  1.00  0.00           N  
HETATM    4  C3  UNL     1       2.689   0.018   0.145  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.221   0.039   0.131  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.525   0.936   0.895  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.869   0.936   0.864  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.534   0.030   0.061  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.931   0.011   0.014  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.726   0.894   0.764  1.00  0.00           C  
HETATM   11  C9  UNL     1      -5.180   0.580   0.459  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.431  -0.855   0.858  1.00  0.00           C  
HETATM   13  C11 UNL     1      -5.495   0.812  -1.002  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.848  -0.880  -0.715  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.545  -1.820  -1.547  1.00  0.00           C  
HETATM   16  N2  UNL     1      -2.089  -2.584  -2.225  1.00  0.00           N  
HETATM   17  C14 UNL     1       0.532  -0.846  -0.654  1.00  0.00           C  
HETATM   18  S1  UNL     1       3.776   1.019   1.039  1.00  0.00           S  
HETATM   19  C15 UNL     1       5.245   0.348   0.488  1.00  0.00           C  
HETATM   20  C16 UNL     1       6.633   0.707   0.831  1.00  0.00           C  
HETATM   21  O2  UNL     1       7.606   0.103   0.327  1.00  0.00           O  
HETATM   22  O3  UNL     1       6.876   1.731   1.727  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.261  -0.937  -1.947  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.327  -2.396  -1.525  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.582  -1.868  -0.395  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.000   1.660   1.536  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.435   1.623   1.449  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.553   0.678   1.834  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.494   1.933   0.475  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.831   1.215   1.092  1.00  0.00           H  
HETATM   31  H9  UNL     1      -6.445  -1.202   0.551  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.262  -0.956   1.938  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.710  -1.484   0.308  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.097  -0.035  -1.598  1.00  0.00           H  
HETATM   35  H13 UNL     1      -5.018   1.754  -1.330  1.00  0.00           H  
HETATM   36  H14 UNL     1      -6.590   0.825  -1.131  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.094  -1.541  -1.247  1.00  0.00           H  
HETATM   38  H16 UNL     1       7.578   2.439   1.602  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   19   19
CONECT    3    4    4
CONECT    4    5   18
CONECT    5    6    6   17
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   14
CONECT    9   10
CONECT   10   11   28   29
CONECT   11   12   13   30
CONECT   12   31   32   33
CONECT   13   34   35   36
CONECT   14   15   17   17
CONECT   15   16   16   16
CONECT   17   37
CONECT   18   19
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   38
END

HMDB0252185
     RDKit          3D
Febuxostat
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.8121   -1.4942   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010   -0.6269   -0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5257   -0.7633   -0.5161 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6895    0.0177    0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    0.0391    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249    0.9355    0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693    0.9355    0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5344    0.0298    0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9312    0.0105    0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261    0.8942    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802    0.5801    0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4307   -0.8553    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4952    0.8122   -1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482   -0.8804   -0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -1.8196   -1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894   -2.5844   -2.2246 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5323   -0.8460   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7755    1.0187    1.0391 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2455    0.3480    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6331    0.7074    0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6058    0.1034    0.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8758    1.7309    1.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2606   -0.9371   -1.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3269   -2.3963   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825   -1.8681   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0003    1.6602    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    1.6230    1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5526    0.6777    1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4940    1.9331    0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8314    1.2147    1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4447   -1.2017    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2625   -0.9561    1.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7098   -1.4841    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0970   -0.0351   -1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0179    1.7544   -1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5897    0.8249   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0944   -1.5415   -1.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5778    2.4390    1.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  3  0
 14 17  2  0
  4 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19  2  2  0
 17  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 17 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic acid	ChEBI
Adenuric	ChEBI
Donifoxate	ChEBI
Febuday	ChEBI
Feburic	ChEBI
Febuxostatum	ChEBI
Goturic	ChEBI
Goutex	ChEBI
TEI 6720	ChEBI
TEI-6720	ChEBI
TMX 67	ChEBI
TMX-67	ChEBI
Uloric	ChEBI
Zurig	ChEBI
2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate	Generator
Donifoxic acid	Generator
2-(3-cyano-4-Isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic acid	MeSH
6720, TEI	MeSH
2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate	Generator

Chemical Formula

C₁₆H₁₆N₂O₃S

Average Molecular Weight

316.375

Monoisotopic Molecular Weight

316.088163078

IUPAC Name

2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid

Traditional Name

febuxostat

CAS Registry Number

Not Available

SMILES

CC(C)COC1=C(C=C(C=C1)C1=NC(C)=C(S1)C(O)=O)C#N

InChI Identifier

InChI=1S/C16H16N2O3S/c1-9(2)8-21-13-5-4-11(6-12(13)7-17)15-18-10(3)14(22-15)16(19)20/h4-6,9H,8H2,1-3H3,(H,19,20)

InChI Key

BQSJTQLCZDPROO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiazolecarboxylic acids and derivatives. These are heterocyclic compounds containing a thiazole ring which bears a carboxylic acid group (or a derivative thereof).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiazoles

Direct Parent

Thiazolecarboxylic acids and derivatives

Alternative Parents

Substituents

2,4,5-trisubstituted 1,3-thiazole
Phenoxy compound
Benzonitrile
Thiazolecarboxylic acid or derivatives
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Carboxylic acid derivative
Azacycle
Carboxylic acid
Ether
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

nitrile (CHEBI:45943 )
1,3-thiazolemonocarboxylic acid (CHEBI:45943 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0252185)

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
logP	3.8	ALOGPS
logP	3.52	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	0.39	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.93 m³·mol⁻¹	ChemAxon
Polarizability	33.88 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
DeepCCS	[M+H]+	177.513	30932474
DeepCCS	[M-H]-	175.155	30932474
DeepCCS	[M-2H]-	208.941	30932474
DeepCCS	[M+Na]+	184.599	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	167.7	32859911
AllCCS	[M+NH4]+	173.5	32859911
AllCCS	[M+Na]+	174.3	32859911
AllCCS	[M-H]-	173.9	32859911
AllCCS	[M+Na-2H]-	173.6	32859911
AllCCS	[M+HCOO]-	173.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	16.2509 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.85 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2273.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	469.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	190.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	233.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	136.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	627.0 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	815.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1268.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	502.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1493.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	407.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	425.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	395.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	533.4 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	46.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Febuxostat	CC(C)COC1=C(C=C(C=C1)C1=NC(C)=C(S1)C(O)=O)C#N	3317.5	Standard polar	33892256
Febuxostat	CC(C)COC1=C(C=C(C=C1)C1=NC(C)=C(S1)C(O)=O)C#N	2493.4	Standard non polar	33892256
Febuxostat	CC(C)COC1=C(C=C(C=C1)C1=NC(C)=C(S1)C(O)=O)C#N	2798.0	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 - Febuxostat GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-4090000000-636b08208913e37cf6c9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Febuxostat GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Febuxostat GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Febuxostat GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Febuxostat LC-ESI-qTof , Positive-QTOF	splash10-03xr-0292000000-d8e012f875d1014fe351	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Febuxostat , positive-QTOF	splash10-03xr-0292000000-d8e012f875d1014fe351	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 10V, Positive-QTOF	splash10-066s-4089000000-c7acf0318016cd20bec2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 20V, Positive-QTOF	splash10-05fr-3091000000-70fc366c85a87b110805	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 40V, Positive-QTOF	splash10-0a4i-9220000000-e6f092b19cb56951c75b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 10V, Negative-QTOF	splash10-00di-0092000000-1d9268ebb0d7e9e4ca73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 20V, Negative-QTOF	splash10-00di-0190000000-8c117b3535dd9b43783a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 40V, Negative-QTOF	splash10-01b9-6390000000-029b21a0f25181f7e081	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 10V, Positive-QTOF	splash10-03xr-2098000000-d7c4d373123c0fe32da1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 20V, Positive-QTOF	splash10-01ox-1090000000-a4e1f7032b3cedd91963	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 40V, Positive-QTOF	splash10-00l6-1290000000-f8dae3e7cfb7130dd262	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 10V, Negative-QTOF	splash10-014i-0091000000-492981b99c59ea00141b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 20V, Negative-QTOF	splash10-014i-0190000000-ee6d6f385111dcd5aae3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Febuxostat 40V, Negative-QTOF	splash10-014i-1390000000-27c92224dda6826d4dd3	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04854

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

Febuxostat

METLIN ID

Not Available

PubChem Compound

134018

PDB ID

Not Available

ChEBI ID

31596

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Febuxostat (HMDB0252185)

MOL for HMDB0252185 (Febuxostat)

3D MOL for HMDB0252185 (Febuxostat)

3D SDF for HMDB0252185 (Febuxostat)

3D-SDF for HMDB0252185 (Febuxostat)

PDB for HMDB0252185 (Febuxostat)

3D PDB for HMDB0252185 (Febuxostat)

SMILES for HMDB0252185 (Febuxostat)

INCHI for HMDB0252185 (Febuxostat)

Structure for HMDB0252185 (Febuxostat)

3D Structure for HMDB0252185 (Febuxostat)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra