NP-MRD: Showing NP-Card for Ethacrynic acid (NP0002622)

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Record Information

Version

2.0

Created at

2020-11-23 18:25:28 UTC

Updated at

2021-08-19 23:59:13 UTC

NP-MRD ID

NP0002622

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ethacrynic acid

Provided By

BMRB

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. 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. In humans, ethacrynic acid is involved in the ethacrynic acid action pathway. Ethacrynic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Ethacrynic acid was first documented in 1994 (PMID: 7932170). Based on a literature review very few articles have been published on Ethacrynic acid (PMID: 34286113) (PMID: 34239398) (PMID: 34156246).

Structure

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


     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.8572    1.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0650    0.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4554   -0.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8458   -0.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8824   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0901   -2.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4920   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842    1.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1062    1.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2888    0.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6793    1.4988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8619    0.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0445   -0.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4349    0.2162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8367   -1.8321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811   -0.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637   -1.4722    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6907   -1.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829   -2.5979    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0398    2.5785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9968    2.1335    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0182    0.9978    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8926   -1.7830    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2830   -2.3458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4086    0.4350    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2362   -1.5182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9805    1.9914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140    3.3443    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7846    1.7588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9392   -0.6065    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0194   -2.7548    0.0000 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  6
  3 23  1  0
  4 24  1  1
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  1
 12 30  1  0
 15 31  1  0
M  END

NP0002622
     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.5153    0.8600   -1.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9782    0.5607   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4186    0.7665   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505   -0.5184    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1234    0.0758    0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6081   -0.2238    1.6063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896   -0.0705    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0271   -1.2592    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348   -1.3117    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1108   -0.1604   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853   -0.2068   -0.2716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6607   -0.2914   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745   -0.8487    0.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0734   -1.2314    1.7745 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8557   -0.9135    0.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    1.0505   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2770    2.5603   -0.3536 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0655    1.0890    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7694    2.6510    0.0772 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797    1.2566   -2.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    0.7539   -2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9216    1.2715   -1.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5266    1.4901    0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6628   -1.0437    0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1854   -1.1697   -0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1983   -0.2183    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6127   -2.1726    0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079   -2.2790    0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9316   -1.0405   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2269    0.6699   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4554   -0.0962    0.4263 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


     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.8572    1.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0650    0.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4554   -0.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8458   -0.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8824   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0901   -2.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4920   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842    1.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1062    1.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2888    0.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6793    1.4988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8619    0.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0445   -0.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4349    0.2162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8367   -1.8321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811   -0.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637   -1.4722    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6907   -1.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4829   -2.5979    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0398    2.5785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9968    2.1335    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0182    0.9978    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8926   -1.7830    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2830   -2.3458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4086    0.4350    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2362   -1.5182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9805    1.9914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140    3.3443    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7846    1.7588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9392   -0.6065    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0194   -2.7548    0.0000 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  6
  3 23  1  0
  4 24  1  1
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  1
 12 30  1  0
 15 31  1  0
M  END
> <DATABASE_ID>
NP0002622

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

NP0002622
     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.5153    0.8600   -1.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9782    0.5607   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4186    0.7665   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505   -0.5184    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1234    0.0758    0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6081   -0.2238    1.6063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896   -0.0705    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0271   -1.2592    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348   -1.3117    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1108   -0.1604   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853   -0.2068   -0.2716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6607   -0.2914   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745   -0.8487    0.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0734   -1.2314    1.7745 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8557   -0.9135    0.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    1.0505   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2770    2.5603   -0.3536 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0655    1.0890    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7694    2.6510    0.0772 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797    1.2566   -2.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    0.7539   -2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9216    1.2715   -1.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5266    1.4901    0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6628   -1.0437    0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1854   -1.1697   -0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1983   -0.2183    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6127   -2.1726    0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079   -2.2790    0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9316   -1.0405   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2269    0.6699   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4554   -0.0962    0.4263 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    NP0002622
HETATM    1  C1  UNL     1      -2.515   0.860  -1.769  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.978   0.561  -0.570  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.419   0.766  -0.295  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.151  -0.518   0.047  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.123   0.076   0.493  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.608  -0.224   1.606  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.690  -0.070   0.294  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.027  -1.259   0.306  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.335  -1.312   0.118  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.111  -0.160  -0.093  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.385  -0.207  -0.272  1.00  0.00           O  
HETATM   12  C10 UNL     1       4.661  -0.291  -0.446  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.475  -0.849   0.696  1.00  0.00           C  
HETATM   14  O3  UNL     1       5.073  -1.231   1.775  1.00  0.00           O  
HETATM   15  O4  UNL     1       6.856  -0.913   0.411  1.00  0.00           O  
HETATM   16  C12 UNL     1       1.401   1.050  -0.098  1.00  0.00           C  
HETATM   17 CL1  UNL     1       2.277   2.560  -0.354  1.00  0.00          CL  
HETATM   18  C13 UNL     1       0.066   1.089   0.087  1.00  0.00           C  
HETATM   19 CL2  UNL     1      -0.769   2.651   0.077  1.00  0.00          CL  
HETATM   20  H1  UNL     1      -3.180   1.257  -2.554  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.493   0.754  -2.099  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.922   1.272  -1.169  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.527   1.490   0.563  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.663  -1.044   0.881  1.00  0.00           H  
HETATM   25  H6  UNL     1      -5.185  -1.170  -0.843  1.00  0.00           H  
HETATM   26  H7  UNL     1      -6.198  -0.218   0.272  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.613  -2.173   0.475  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.808  -2.279   0.142  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.932  -1.040  -1.284  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.227   0.670  -0.693  1.00  0.00           H  
HETATM   31  H12 UNL     1       7.455  -0.096   0.426  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

NP0002622
     RDKit          3D

31 31  0  0  0  0  0  0  0  0999 V2000
   -2.5153    0.8600   -1.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9782    0.5607   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4186    0.7665   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505   -0.5184    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1234    0.0758    0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6081   -0.2238    1.6063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896   -0.0705    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0271   -1.2592    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348   -1.3117    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1108   -0.1604   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853   -0.2068   -0.2716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6607   -0.2914   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745   -0.8487    0.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0734   -1.2314    1.7745 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8557   -0.9135    0.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    1.0505   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2770    2.5603   -0.3536 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0655    1.0890    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7694    2.6510    0.0772 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797    1.2566   -2.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    0.7539   -2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9216    1.2715   -1.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5266    1.4901    0.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6628   -1.0437    0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1854   -1.1697   -0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1983   -0.2183    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6127   -2.1726    0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079   -2.2790    0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9316   -1.0405   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2269    0.6699   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4554   -0.0962    0.4263 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

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 Mass

303.1380 Da

Monoisotopic Mass

302.01126 Da

IUPAC Name

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

Traditional Name

ethacrynic acid

CAS Registry Number

Not Available

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	197.00 to 198.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	179.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.638 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0015039

DrugBank ID

DB00903

Phenol Explorer Compound ID

Not Available

FoodDB 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

PDB ID

ChEBI ID

Good Scents ID

References

General References

Lacreta FP, Brennan JM, Nash SL, Comis RL, Tew KD, O'Dwyer PJ: Pharmakokinetics and bioavailability study of ethacrynic acid as a modulator of drug resistance in patients with cancer. J Pharmacol Exp Ther. 1994 Sep;270(3):1186-91. [PubMed:7932170 ]
Ismail A, Sawmi J, Mannervik B: Marmoset glutathione transferases with ketosteroid isomerase activity. Biochem Biophys Rep. 2021 Jul 12;27:101078. doi: 10.1016/j.bbrep.2021.101078. eCollection 2021 Sep. [PubMed:34286113 ]
Moffett BS, Kulik K, Khichi M, Arikan A: Acetazolamide-Associated Acute Kidney Injury in Critically Ill Pediatric Patients. J Pediatr Pharmacol Ther. 2021;26(5):467-471. doi: 10.5863/1551-6776-26.5.467. Epub 2021 Jun 28. [PubMed:34239398 ]
Biancalana L, Kostrhunova H, Batchelor LK, Hadiji M, Degano I, Pampaloni G, Zacchini S, Dyson PJ, Brabec V, Marchetti F: Hetero-Bis-Conjugation of Bioactive Molecules to Half-Sandwich Ruthenium(II) and Iridium(III) Complexes Provides Synergic Effects in Cancer Cell Cytotoxicity. Inorg Chem. 2021 Jul 5;60(13):9529-9541. doi: 10.1021/acs.inorgchem.1c00641. Epub 2021 Jun 22. [PubMed:34156246 ]

Showing NP-Card for Ethacrynic acid (NP0002622)

MOL for NP0002622 (Ethacrynic acid)

3D MOL for NP0002622 (Ethacrynic acid)

3D SDF for NP0002622 (Ethacrynic acid)

3D-SDF for NP0002622 (Ethacrynic acid)

PDB for NP0002622 (Ethacrynic acid)

3D PDB for NP0002622 (Ethacrynic acid)

SMILES for NP0002622 (Ethacrynic acid)

INCHI for NP0002622 (Ethacrynic acid)

Structure for NP0002622 (Ethacrynic acid)

3D Structure for NP0002622 (Ethacrynic acid)