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enzymes (2)transporters (2) Show 4 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 02:51:50 UTC

HMDB ID

HMDB0015039

Secondary Accession Numbers

HMDB15039

Metabolite Identification

Common Name

Ethacrynic acid

Description

Ethacrynic acid, also known as ethacrynate or edecrina, belongs to the class of organic compounds known as chlorophenoxyacetates. Chlorophenoxyacetates are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC2.5.1.18) inhibitor. Ethacrynic acid is a drug which is used for the treatment of high blood pressure and edema caused by diseases like congestive heart failure, liver failure, and kidney failure. Ethacrynic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). ethacrynic acid can be converted into ethacrynic acid; which is catalyzed by the enzyme solute carrier family 22 member 6. In humans, ethacrynic acid is involved in ethacrynic acid action pathway. An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4.

Structure

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

HMDB0015039
     RDKit          3D
Ethacrynic acid
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.7182    0.5072   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126   -0.4041    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9734   -0.8290    1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048   -0.1400    0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691   -1.0221    0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028   -1.8812    1.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1771   -0.6502    0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7910    0.0288    0.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    0.3986    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2645    0.0869   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4581    0.4494   -1.4907 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4438    1.1222   -0.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9393    0.2576    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7759    0.6629    1.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4552   -1.0416    0.4181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049   -0.5945   -1.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671   -0.9783   -3.2881 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1029   -0.9520   -1.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345   -1.8356   -1.9872 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6241    0.9550   -0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726    0.8440   -1.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1097   -1.9362    1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808   -0.5841    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0470   -0.2512    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4937   -0.4919   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0288    0.9509    0.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6324    0.2988    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279    0.9556    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2825    1.3472   -1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0819    2.1005   -0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8192   -1.7931   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  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  1  0
 13 14  2  0
 13 15  1  0
 10 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 15 31  1  0
M  END

903
  Mrv0541 02231215052D          

 19 19  0  0  0  0            999 V2000
    1.6500    1.0808    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.5693    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.3183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 14  1  0  0  0  0
  3 13  1  0  0  0  0
  3 18  1  0  0  0  0
  4  9  2  0  0  0  0
  5 19  1  0  0  0  0
  6 19  2  0  0  0  0
  7  9  1  0  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 17  2  0  0  0  0
 10 16  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015039

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)

> <INCHI_KEY>
AVOLMBLBETYQHX-UHFFFAOYSA-N

> <FORMULA>
C13H12Cl2O4

> <MOLECULAR_WEIGHT>
303.138

> <EXACT_MASS>
302.011264286

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.569602930770436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
3.655706891333333

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7969337828715655

> <JCHEM_PKA_STRONGEST_BASIC>
-4.96222290828044

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
72.224

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethacrynic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015039
     RDKit          3D
Ethacrynic acid
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.7182    0.5072   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126   -0.4041    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9734   -0.8290    1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048   -0.1400    0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691   -1.0221    0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028   -1.8812    1.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1771   -0.6502    0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7910    0.0288    0.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    0.3986    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2645    0.0869   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4581    0.4494   -1.4907 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4438    1.1222   -0.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9393    0.2576    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7759    0.6629    1.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4552   -1.0416    0.4181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049   -0.5945   -1.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671   -0.9783   -3.2881 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1029   -0.9520   -1.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345   -1.8356   -1.9872 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6241    0.9550   -0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726    0.8440   -1.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1097   -1.9362    1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808   -0.5841    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0470   -0.2512    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4937   -0.4919   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0288    0.9509    0.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6324    0.2988    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279    0.9556    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2825    1.3472   -1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0819    2.1005   -0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8192   -1.7931   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  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  1  0
 13 14  2  0
 13 15  1  0
 10 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 903                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080   2.017   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       3.080  -1.063   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       5.748  -2.603   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414   4.327   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.415  -5.683   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.748  -5.683   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.748   2.017   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   4.327   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748   3.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   5.867   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   1.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   1.247   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -1.063   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -0.293   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -0.293   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   6.637   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   3.557   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -3.373   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081  -4.913   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   14                                                            
CONECT    3   13   18                                                       
CONECT    4    9                                                            
CONECT    5   19                                                            
CONECT    6   19                                                            
CONECT    7    9   11   12                                                  
CONECT    8    9   10   17                                                  
CONECT    9    4    7    8                                                  
CONECT   10    8   16                                                       
CONECT   11    1    7   14                                                  
CONECT   12    7   15                                                       
CONECT   13    3   14   15                                                  
CONECT   14    2   11   13                                                  
CONECT   15   12   13                                                       
CONECT   16   10                                                            
CONECT   17    8                                                            
CONECT   18    3   19                                                       
CONECT   19    5    6   18                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0015039
HETATM    1  C1  UNL     1      -2.718   0.507  -0.554  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.713  -0.404   0.395  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.973  -0.829   1.013  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.205  -0.140   0.490  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.469  -1.022   0.865  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.503  -1.881   1.764  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.177  -0.650   0.296  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.791   0.029   0.997  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.002   0.399   0.418  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.265   0.087  -0.895  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.458   0.449  -1.491  1.00  0.00           O  
HETATM   12  C10 UNL     1       4.444   1.122  -0.757  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.939   0.258   0.332  1.00  0.00           C  
HETATM   14  O3  UNL     1       5.776   0.663   1.168  1.00  0.00           O  
HETATM   15  O4  UNL     1       4.455  -1.042   0.418  1.00  0.00           O  
HETATM   16  C12 UNL     1       1.305  -0.594  -1.614  1.00  0.00           C  
HETATM   17 CL1  UNL     1       1.667  -0.978  -3.288  1.00  0.00          CL  
HETATM   18  C13 UNL     1       0.103  -0.952  -1.009  1.00  0.00           C  
HETATM   19 CL2  UNL     1      -1.034  -1.836  -1.987  1.00  0.00          CL  
HETATM   20  H1  UNL     1      -3.624   0.955  -0.898  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.773   0.844  -1.018  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.110  -1.936   1.003  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.881  -0.584   2.106  1.00  0.00           H  
HETATM   24  H5  UNL     1      -6.047  -0.251   1.226  1.00  0.00           H  
HETATM   25  H6  UNL     1      -5.494  -0.492  -0.517  1.00  0.00           H  
HETATM   26  H7  UNL     1      -5.029   0.951   0.452  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.632   0.299   2.041  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.728   0.956   1.035  1.00  0.00           H  
HETATM   29  H10 UNL     1       5.283   1.347  -1.467  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.082   2.100  -0.365  1.00  0.00           H  
HETATM   31  H12 UNL     1       4.819  -1.793  -0.159  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3    5
CONECT    3    4   22   23
CONECT    4   24   25   26
CONECT    5    6    6    7
CONECT    7    8    8   18
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   16
CONECT   11   12
CONECT   12   13   29   30
CONECT   13   14   14   15
CONECT   15   31
CONECT   16   17   18   18
CONECT   18   19
END

HMDB0015039
     RDKit          3D
Ethacrynic acid
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.7182    0.5072   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126   -0.4041    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9734   -0.8290    1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2048   -0.1400    0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691   -1.0221    0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028   -1.8812    1.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1771   -0.6502    0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7910    0.0288    0.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    0.3986    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2645    0.0869   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4581    0.4494   -1.4907 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4438    1.1222   -0.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9393    0.2576    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7759    0.6629    1.1684 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4552   -1.0416    0.4181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049   -0.5945   -1.6135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671   -0.9783   -3.2881 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1029   -0.9520   -1.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345   -1.8356   -1.9872 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6241    0.9550   -0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726    0.8440   -1.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1097   -1.9362    1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808   -0.5841    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0470   -0.2512    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4937   -0.4919   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0288    0.9509    0.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6324    0.2988    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279    0.9556    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2825    1.3472   -1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0819    2.1005   -0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8192   -1.7931   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  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  1  0
 13 14  2  0
 13 15  1  0
 10 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid	ChEBI
Acide etacrynique	ChEBI
Acido etacrinico	ChEBI
Acidum etacrynicum	ChEBI
Crinuryl	ChEBI
Edecril	ChEBI
Edecrina	ChEBI
Endecril	ChEBI
Etacrinic acid	ChEBI
Ethacrynate	ChEBI
Hidromedin	ChEBI
Hydromedin	ChEBI
Methylenebutyrylphenoxyacetic acid	ChEBI
Mingit	ChEBI
Otacril	ChEBI
Reomax	ChEBI
Taladren	ChEBI
Uregit	ChEBI
Etacrynic acid	Kegg
(2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetate	Generator
Etacrinate	Generator
Methylenebutyrylphenoxyacetate	Generator
Etacrynate	Generator
Etakrinic acid	HMDB
Ethacryinic acid	HMDB
Acid, ethacrinic	HMDB
Ethacrinic acid	HMDB
Ethacrynate sodium	HMDB
Ethacrynic acid, sodium salt	HMDB
Sodium, ethacrynate	HMDB
Acid, etacrynic	HMDB
Acid, ethacrynic	HMDB
Edecrin	HMDB

Chemical Formula

C₁₃H₁₂Cl₂O₄

Average Molecular Weight

303.138

Monoisotopic Molecular Weight

302.011264286

IUPAC Name

2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid

Traditional Name

ethacrynic acid

CAS Registry Number

58-54-8

SMILES

CCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1

InChI Identifier

InChI=1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)

InChI Key

AVOLMBLBETYQHX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorophenoxyacetates. Chlorophenoxyacetates are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Chlorophenoxyacetates

Alternative Parents

Substituents

Chlorophenoxyacetate
Butyrophenone
1,2-dichlorobenzene
Phenoxy compound
Benzoyl
Phenol ether
Aryl ketone
Halobenzene
Chlorobenzene
Alkyl aryl ether
Aryl halide
Alpha-branched alpha,beta-unsaturated-ketone
Aryl chloride
Alpha,beta-unsaturated ketone
Enone
Vinylogous halide
Acryloyl-group
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Ether
Organic oxygen compound
Carbonyl group
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:4876 )
monocarboxylic acid (CHEBI:4876 )
dichlorobenzene (CHEBI:4876 )
aromatic ketone (CHEBI:4876 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	122.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.019 g/L	Not Available
LogP	3.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	3.42	ALOGPS
logP	3.66	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.8	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.22 m³·mol⁻¹	ChemAxon
Polarizability	28.57 Å³	ChemAxon
Number of Rings	1	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]+	168.995	30932474
DeepCCS	[M-H]-	166.637	30932474
DeepCCS	[M-2H]-	199.523	30932474
DeepCCS	[M+Na]+	175.088	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	166.0	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	161.9	32859911
AllCCS	[M+HCOO]-	162.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.55 minutes	32390414
Predicted by Siyang on May 30, 2022	17.0232 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.72 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2318.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	537.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	190.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	327.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	240.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	647.9 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	825.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	168.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1358.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	529.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1677.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	529.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	460.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	549.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	436.7 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	89.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethacrynic acid	CCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1	3624.3	Standard polar	33892256
Ethacrynic acid	CCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1	2146.8	Standard non polar	33892256
Ethacrynic acid	CCC(=C)C(=O)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1	2319.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethacrynic acid,1TMS,isomer #1	C=C(CC)C(=O)C1=CC=C(OCC(=O)O[Si](C)(C)C)C(Cl)=C1Cl	2298.0	Semi standard non polar	33892256
Ethacrynic acid,1TBDMS,isomer #1	C=C(CC)C(=O)C1=CC=C(OCC(=O)O[Si](C)(C)C(C)(C)C)C(Cl)=C1Cl	2546.8	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 - Ethacrynic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-05mo-7090000000-ad262bb070e8e48d2d63	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethacrynic acid GC-MS (1 TMS) - 70eV, Positive	splash10-062i-9012000000-fbc841e49aad01b35c49	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethacrynic acid 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 - Ethacrynic acid LC-ESI-qTof , Positive-QTOF	splash10-0a4i-0690000000-f598b8bee69a6b62e817	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethacrynic acid , positive-QTOF	splash10-0a4i-0690000000-f598b8bee69a6b62e817	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ethacrynic acid , positive-QTOF	splash10-0fb9-2930000000-143e32f52c12761e81dd	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 10V, Positive-QTOF	splash10-0f89-9036000000-649cbeb1b954b158866f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 20V, Positive-QTOF	splash10-0f8i-9084000000-84c8027d849b76f0fc82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 40V, Positive-QTOF	splash10-0ue9-9000000000-a3a5b075c90ba85c8e90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 10V, Negative-QTOF	splash10-0udi-0029000000-21fb3e922a0d4368b160	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 20V, Negative-QTOF	splash10-0udi-1095000000-7cbed97a8be9a8a9c7dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 40V, Negative-QTOF	splash10-000i-4690000000-87b7486401d3036ea50c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 10V, Positive-QTOF	splash10-0udi-0059000000-51c16f82d9d3dcd362d6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 20V, Positive-QTOF	splash10-0udr-2095000000-984d8aafed69f00c25bf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 40V, Positive-QTOF	splash10-022c-4950000000-fd4ac1ee6524d2082199	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 10V, Negative-QTOF	splash10-0udi-0039000000-dd7be49fbec8d532bd2d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 20V, Negative-QTOF	splash10-0f89-9086000000-b20750e2d0d1b3645cb1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethacrynic acid 40V, Negative-QTOF	splash10-0543-6490000000-fb32fecaea2c34a668a6	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Ethacrynic Acid Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00903	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00903	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00903

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Etacrynic_acid

METLIN ID

Not Available

PubChem Compound

3278

PDB ID

EAA

ChEBI ID

4876

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)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Glutathione S-transferase A2

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTA2
Uniprot ID:: P09210
Molecular weight:: 25663.675

References

Depeille P, Cuq P, Passagne I, Evrard A, Vian L: Combined effects of GSTP1 and MRP1 in melanoma drug resistance. Br J Cancer. 2005 Jul 25;93(2):216-23. [PubMed:15999103 ]
Awasthi S, Srivastava SK, Ahmad F, Ahmad H, Ansari GA: Interactions of glutathione S-transferase-pi with ethacrynic acid and its glutathione conjugate. Biochim Biophys Acta. 1993 Jul 10;1164(2):173-8. [PubMed:8329448 ]
Iersel ML, Ploemen JP, Struik I, van Amersfoort C, Keyzer AE, Schefferlie JG, van Bladeren PJ: Inhibition of glutathione S-transferase activity in human melanoma cells by alpha,beta-unsaturated carbonyl derivatives. Effects of acrolein, cinnamaldehyde, citral, crotonaldehyde, curcumin, ethacrynic acid, and trans-2-hexenal. Chem Biol Interact. 1996 Oct 21;102(2):117-32. [PubMed:8950226 ]
van Iersel ML, Ploemen JP, Lo Bello M, Federici G, van Bladeren PJ: Interactions of alpha, beta-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1. Chem Biol Interact. 1997 Dec 12;108(1-2):67-78. [PubMed:9463521 ]
Morrow CS, Smitherman PK, Townsend AJ: Combined expression of multidrug resistance protein (MRP) and glutathione S-transferase P1-1 (GSTP1-1) in MCF7 cells and high level resistance to the cytotoxicities of ethacrynic acid but not oxazaphosphorines or cisplatin. Biochem Pharmacol. 1998 Oct 15;56(8):1013-21. [PubMed:9776312 ]

Enzyme Details

2. Sodium/potassium-transporting ATPase subunit alpha-1

General function:: Involved in ATP binding
Specific function:: This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:: ATP1A1
Uniprot ID:: P05023
Molecular weight:: 112895.01

References

Ronquist G, Agren GK: A Mg2+- and Ca2+-stimulated adenosine triphosphatase at the outer surface of Ehrlich ascites tumor cells. Cancer Res. 1975 Jun;35(6):1402-6. [PubMed:124205 ]
Proverbio F, Condrescu-Guidi M, Whittembury G: Ouabain-insensitive Na+ stimulation of an Mg-2+ -dependent ATPase in kidney tissue. Biochim Biophys Acta. 1975 Jun 25;394(2):281-92. [PubMed:124600 ]
Valdes RM, Huff MO, El-Masri MA, El-Mallakh RS: Effect of ethacrynic acid on sodium pump alpha isoforms in SH-SY5Y cells. Bipolar Disord. 2003 Apr;5(2):123-8. [PubMed:12680902 ]
Kiil F, Sejersted OM: Analysis of energy metabolism and mechanism of loop diuretics in the thick ascending limb of Henle's loop in dog kidneys. Acta Physiol Scand. 2003 May;178(1):73-82. [PubMed:12713517 ]
Schurek HJ, Aulbert E, Ebel H, Muller-Suur C: Influence of ouabain and ethacrynic acid on sodium transport and NaK-ATPase activity in the isolated perfused rat kidney. Curr Probl Clin Biochem. 1975;4:162-8. [PubMed:127690 ]

Transporters

Enzyme Details

1. Solute carrier family 12 member 1

General function:: Involved in transport
Specific function:: Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume
Gene Name:: SLC12A1
Uniprot ID:: Q13621
Molecular weight:: 121449.1

References

Bowes TJ, Gupta RS: Induction of mitochondrial fusion by cysteine-alkylators ethacrynic acid and N-ethylmaleimide. J Cell Physiol. 2005 Mar;202(3):796-804. [PubMed:15389563 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Sekine T, Watanabe N, Hosoyamada M, Kanai Y, Endou H: Expression cloning and characterization of a novel multispecific organic anion transporter. J Biol Chem. 1997 Jul 25;272(30):18526-9. [PubMed:9228014 ]

Showing metabocard for Ethacrynic acid (HMDB0015039)

MOL for HMDB0015039 (Ethacrynic acid)

3D MOL for HMDB0015039 (Ethacrynic acid)

3D SDF for HMDB0015039 (Ethacrynic acid)

3D-SDF for HMDB0015039 (Ethacrynic acid)

PDB for HMDB0015039 (Ethacrynic acid)

3D PDB for HMDB0015039 (Ethacrynic acid)

SMILES for HMDB0015039 (Ethacrynic acid)

INCHI for HMDB0015039 (Ethacrynic acid)

Structure for HMDB0015039 (Ethacrynic acid)

3D Structure for HMDB0015039 (Ethacrynic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

Transporters

References

References