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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:41:48 UTC

Update Date

2022-03-07 02:57:12 UTC

HMDB ID

HMDB0041834

Secondary Accession Numbers

HMDB41834

Metabolite Identification

Common Name

Benzbromarone

Description

Benzbromarone (INN) is a uricosuric agent used in the treatment of gout, especially when allopurinol, a first-line treatment, fails or produces intolerable adverse effects. It is structurally related to the antiarrhythmic amiodarone. Benzbromarone is a very potent inhibitor of CYP2C9. Several analogues of the drug have been developed as CYP2C9 and CYP2C19 inhibitors for use in research.

Structure

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

HMDB0041834
     RDKit          3D
Benzbromarone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -0.4350   -2.9622   -1.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6786   -2.6869   -0.8321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9267   -1.2562   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8952   -0.4914   -0.9583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8466    0.7175   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6363    1.8432   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    3.0154   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2654    3.1181    0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4965    1.9941    0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7470    0.7851    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582   -0.4527    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0259   -0.8776    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -1.7581    1.9199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3912   -0.4017    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744   -1.2175    1.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786   -0.8029    0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2517   -1.9536    1.3538 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.0762    0.4302    0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3937    0.8602    0.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204    1.2401   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4178    2.9595   -0.7471 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7007    0.8129    0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301   -4.0384   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487   -2.3726   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898   -2.9743   -2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -3.3579    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5244   -2.9736   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4902    1.7547   -1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0431    3.8753   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0343    4.0551    1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367    2.0593    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364   -2.1871    1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6660    1.7452   -0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351    1.4992   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  3  2  0
 22 14  1  0
 10  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 15 32  1  0
 19 33  1  0
 22 34  1  0
M  END


  Mrv0541 09131211412D          

 22 24  0  0  0  0            999 V2000
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -1.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -0.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -1.8414    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342    0.9540    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -0.6152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  2  1  0  0  0  0
 14  6  2  0  0  0  0
 14 10  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 16  2  0  0  0  0
 21 17  1  0  0  0  0
 22 13  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041834

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=C(C(=O)C2=CC(Br)=C(O)C(Br)=C2)C2=CC=CC=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12Br2O3/c1-2-13-15(10-5-3-4-6-14(10)22-13)16(20)9-7-11(18)17(21)12(19)8-9/h3-8,21H,2H2,1H3

> <INCHI_KEY>
WHQCHUCQKNIQEC-UHFFFAOYSA-N

> <FORMULA>
C17H12Br2O3

> <MOLECULAR_WEIGHT>
424.083

> <EXACT_MASS>
421.915319544

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.64614561636836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dibromo-4-(2-ethyl-1-benzofuran-3-carbonyl)phenol

> <ALOGPS_LOGP>
5.52

> <JCHEM_LOGP>
5.547745900999999

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.11079144308044

> <JCHEM_PKA_STRONGEST_BASIC>
-3.842504364936835

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
92.37480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzbromarone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041834
     RDKit          3D
Benzbromarone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -0.4350   -2.9622   -1.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6786   -2.6869   -0.8321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9267   -1.2562   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8952   -0.4914   -0.9583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8466    0.7175   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6363    1.8432   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    3.0154   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2654    3.1181    0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4965    1.9941    0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7470    0.7851    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582   -0.4527    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0259   -0.8776    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -1.7581    1.9199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3912   -0.4017    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744   -1.2175    1.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786   -0.8029    0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2517   -1.9536    1.3538 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.0762    0.4302    0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3937    0.8602    0.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204    1.2401   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4178    2.9595   -0.7471 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7007    0.8129    0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301   -4.0384   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487   -2.3726   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898   -2.9743   -2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -3.3579    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5244   -2.9736   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4902    1.7547   -1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0431    3.8753   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0343    4.0551    1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367    2.0593    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364   -2.1871    1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6660    1.7452   -0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351    1.4992   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  3  2  0
 22 14  1  0
 10  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 15 32  1  0
 19 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -1.090   4.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.332  -1.653   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.887   0.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.839  -1.973   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.393   0.636   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.869  -0.828   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      -2.315  -3.437   0.000  0.00  0.00          Br+0
HETATM   19 Br   UNK     0      -3.424   1.781   0.000  0.00  0.00          Br+0
HETATM   20  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.376  -1.148   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   13                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   14                                                       
CONECT    7    9   11                                                       
CONECT    8    9   12                                                       
CONECT    9    7    8   16                                                  
CONECT   10    5   14   15                                                  
CONECT   11    7   17   18                                                  
CONECT   12    8   17   19                                                  
CONECT   13    2   15   22                                                  
CONECT   14    6   10   22                                                  
CONECT   15   10   13   16                                                  
CONECT   16    9   15   20                                                  
CONECT   17   11   12   21                                                  
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0041834
HETATM    1  C1  UNL     1      -0.435  -2.962  -1.592  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.679  -2.687  -0.832  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.927  -1.256  -0.524  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.895  -0.491  -0.958  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.847   0.717  -0.488  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.636   1.843  -0.652  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.367   3.015  -0.026  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.265   3.118   0.814  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.496   1.994   0.963  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.747   0.785   0.338  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.158  -0.453   0.320  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.026  -0.878   0.991  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.082  -1.758   1.920  1.00  0.00           O  
HETATM   14  C12 UNL     1       1.391  -0.402   0.730  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.474  -1.218   1.074  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.779  -0.803   0.883  1.00  0.00           C  
HETATM   17 BR1  UNL     1       5.252  -1.954   1.354  1.00  0.00          BR  
HETATM   18  C15 UNL     1       4.076   0.430   0.342  1.00  0.00           C  
HETATM   19  O3  UNL     1       5.394   0.860   0.149  1.00  0.00           O  
HETATM   20  C16 UNL     1       3.020   1.240  -0.001  1.00  0.00           C  
HETATM   21 BR2  UNL     1       3.418   2.959  -0.747  1.00  0.00          BR  
HETATM   22  C17 UNL     1       1.701   0.813   0.199  1.00  0.00           C  
HETATM   23  H1  UNL     1      -0.130  -4.038  -1.355  1.00  0.00           H  
HETATM   24  H2  UNL     1       0.449  -2.373  -1.264  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.590  -2.974  -2.684  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.833  -3.358   0.050  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.524  -2.974  -1.573  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.490   1.755  -1.310  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.043   3.875  -0.203  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.034   4.055   1.318  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.637   2.059   1.625  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.236  -2.187   1.490  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.666   1.745  -0.235  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.935   1.499  -0.116  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   11   11
CONECT    4    5
CONECT    5    6    6   10
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   22
CONECT   15   16   32
CONECT   16   17   18   18
CONECT   18   19   20
CONECT   19   33
CONECT   20   21   22   22
CONECT   22   34
END

HMDB0041834
     RDKit          3D
Benzbromarone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -0.4350   -2.9622   -1.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6786   -2.6869   -0.8321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9267   -1.2562   -0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8952   -0.4914   -0.9583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8466    0.7175   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6363    1.8432   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    3.0154   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2654    3.1181    0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4965    1.9941    0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7470    0.7851    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582   -0.4527    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0259   -0.8776    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -1.7581    1.9199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3912   -0.4017    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744   -1.2175    1.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786   -0.8029    0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2517   -1.9536    1.3538 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.0762    0.4302    0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3937    0.8602    0.1490 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204    1.2401   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4178    2.9595   -0.7471 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7007    0.8129    0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301   -4.0384   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487   -2.3726   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5898   -2.9743   -2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -3.3579    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5244   -2.9736   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4902    1.7547   -1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0431    3.8753   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0343    4.0551    1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367    2.0593    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364   -2.1871    1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6660    1.7452   -0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351    1.4992   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  3  2  0
 22 14  1  0
 10  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 15 32  1  0
 19 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Ethyl-3-(3,5-dibrom-4-hydroxybenzoyl)benzofuran	ChEBI
3,5-Dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone	ChEBI
Uroleap	ChEBI
(3,5-Dibromo-4-hydroxyphenyl)(2-ethyl-1-benzofuran-3-yl)methanone	HMDB
3, 5-Dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone	HMDB
Benzbromaron	HMDB
Benzbromarone(usan)	HMDB
Desuric	HMDB
Exurate	HMDB
Hipurik	HMDB
Ketone, 3,5-dibromo-4-hydroxyphenyl 2-ethyl-3-benzofuranyl	HMDB
L 2214-Labaz	HMDB
Minuric	HMDB
Normurat	HMDB
Uricovac	HMDB
Urinorm	HMDB
AL, benzbromaron	HMDB
Aliud brand OF benzbromarone	HMDB
Benzbromaron al	HMDB
Besuric	HMDB
Sanfer brand OF benzbromarone	HMDB
Ratiopharm brand OF benzbromarone	HMDB
Acifugan	HMDB
Benzbromaronratiopharm	HMDB
Heumann brand OF benzbromarone	HMDB
Benzbromaron ratiopharm	HMDB
Benzbromarone aliud brand	HMDB
Benzbromarone heumann brand	HMDB
Benzbromarone sanfer brand	HMDB
Benzbromarone ratiopharm brand	HMDB
Narcaricin	HMDB
Sanofi winthrop brand OF benzbromarone	HMDB
Benzbromaron-ratiopharm	HMDB

Chemical Formula

C₁₇H₁₂Br₂O₃

Average Molecular Weight

424.083

Monoisotopic Molecular Weight

421.915319544

IUPAC Name

2,6-dibromo-4-(2-ethyl-1-benzofuran-3-carbonyl)phenol

Traditional Name

benzbromarone

CAS Registry Number

3562-84-3

SMILES

CCC1=C(C(=O)C2=CC(Br)=C(O)C(Br)=C2)C2=CC=CC=C2O1

InChI Identifier

InChI=1S/C17H12Br2O3/c1-2-13-15(10-5-3-4-6-14(10)22-13)16(20)9-7-11(18)17(21)12(19)8-9/h3-8,21H,2H2,1H3

InChI Key

WHQCHUCQKNIQEC-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
Benzofuran
3-aroylfuran
Benzoyl
2-bromophenol
2-halophenol
Phenol
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organobromide
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzofurans (CHEBI:3023 )
aromatic ketone (CHEBI:3023 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041834)

Source

Exogenous

Exogenous (HMDB: HMDB0041834)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	151 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	5.52	ALOGPS
logP	5.55	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	5.11	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.37 m³·mol⁻¹	ChemAxon
Polarizability	35.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	170.614	30932474
DeepCCS	[M-H]-	168.256	30932474
DeepCCS	[M-2H]-	202.026	30932474
DeepCCS	[M+Na]+	177.254	30932474
AllCCS	[M+H]+	186.0	32859911
AllCCS	[M+H-H2O]+	183.1	32859911
AllCCS	[M+NH4]+	188.8	32859911
AllCCS	[M+Na]+	189.5	32859911
AllCCS	[M-H]-	171.7	32859911
AllCCS	[M+Na-2H]-	171.5	32859911
AllCCS	[M+HCOO]-	171.5	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.	8.62 minutes	32390414
Predicted by Siyang on May 30, 2022	19.8816 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.77 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2721.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	678.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	260.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	416.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	430.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	758.4 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	869.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	77.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1649.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	708.4 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	1787.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	649.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	521.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	461.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	431.5 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	22.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzbromarone	CCC1=C(C(=O)C2=CC(Br)=C(O)C(Br)=C2)C2=CC=CC=C2O1	3740.6	Standard polar	33892256
Benzbromarone	CCC1=C(C(=O)C2=CC(Br)=C(O)C(Br)=C2)C2=CC=CC=C2O1	2761.2	Standard non polar	33892256
Benzbromarone	CCC1=C(C(=O)C2=CC(Br)=C(O)C(Br)=C2)C2=CC=CC=C2O1	2798.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzbromarone,1TMS,isomer #1	CCC1=C(C(=O)C2=CC(Br)=C(O[Si](C)(C)C)C(Br)=C2)C2=CC=CC=C2O1	2987.1	Semi standard non polar	33892256
Benzbromarone,1TBDMS,isomer #1	CCC1=C(C(=O)C2=CC(Br)=C(O[Si](C)(C)C(C)(C)C)C(Br)=C2)C2=CC=CC=C2O1	3252.2	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 - Benzbromarone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i1-4832900000-7ab986576555401c2682	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzbromarone GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9503700000-00cd0af3f4c2c3b65960	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzbromarone 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 - Benzbromarone 35V, Negative-QTOF	splash10-00di-0000900000-94d07af34f38fb48d939	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 10V, Positive-QTOF	splash10-00di-0120900000-fc249a1eb88559bbcbb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 20V, Positive-QTOF	splash10-00b9-0591400000-e59e173f15483ef2be8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 40V, Positive-QTOF	splash10-004j-1290000000-c6ab434e069c23434652	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 10V, Negative-QTOF	splash10-00di-0000900000-65ce336d84ac3bc1b6cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 20V, Negative-QTOF	splash10-00di-0332900000-1e5e89c78006263a0948	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 40V, Negative-QTOF	splash10-0005-2931000000-017d942ea5bfdf5d7a10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 10V, Negative-QTOF	splash10-00di-0000900000-dacd5da7c3b80a31dd02	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 20V, Negative-QTOF	splash10-00di-4000900000-8beeba5ecf13d3cdd46c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 40V, Negative-QTOF	splash10-004i-9000000000-abb69a363cc923ebb9e1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 10V, Positive-QTOF	splash10-00di-0000900000-2199f895a98ec54296c3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 20V, Positive-QTOF	splash10-00fr-0180900000-6045f757598f9ed9a40f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzbromarone 40V, Positive-QTOF	splash10-004l-1590000000-09a3248599d038d0c11b	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB12319

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2243

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzbromarone

METLIN ID

Not Available

PubChem Compound

2333

PDB ID

Not Available

ChEBI ID

3023

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Benzbromarone (HMDB0041834)

MOL for HMDB0041834 (Benzbromarone)

3D MOL for HMDB0041834 (Benzbromarone)

3D SDF for HMDB0041834 (Benzbromarone)

3D-SDF for HMDB0041834 (Benzbromarone)

PDB for HMDB0041834 (Benzbromarone)

3D PDB for HMDB0041834 (Benzbromarone)

SMILES for HMDB0041834 (Benzbromarone)

INCHI for HMDB0041834 (Benzbromarone)

Structure for HMDB0041834 (Benzbromarone)

3D Structure for HMDB0041834 (Benzbromarone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra