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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014946

Secondary Accession Numbers

HMDB14946

Metabolite Identification

Common Name

Indapamide

Description

Indapamide is only found in individuals that have used or taken this drug. It is a benzamide-sulfonamide-indole. It is called a thiazide-like diuretic but structure is different enough (lacking the thiazo-ring) so it is not clear that the mechanism is comparable. [PubChem]Indapamide blocks the slow component of delayed rectifier potassium current (IKs) without altering the rapid component (IKr) or the inward rectifier current. Specifically it blocks or antagonizes the action the proteins KCNQ1 and KCNE1. Indapamide is also thought to stimulate the synthesis of the vasodilatory hypotensive prostaglandin PGE2.

Structure

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

HMDB0014946
     RDKit          3D
Indapamide
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.1668   -2.9606    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -1.9066    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073   -1.8813   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8283   -0.4982   -0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0582    0.0402   -0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2387    1.3841   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277    2.1706   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9997    1.6198    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815    0.2703   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.5689    0.1441 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3143   -0.1750    0.1649 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2902    0.5782    1.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3861    0.9441    2.1678 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6897    0.9379    1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2297    2.0307    1.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5774    2.3008    1.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4130    1.4836    0.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1317    1.8436    0.7136 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8851    0.3914    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8799   -0.6546   -0.7269 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.6337    0.1312   -2.0485 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9726   -1.2843    0.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0657   -1.8161   -1.2669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5220    0.1308    0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7096   -3.8509   -0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -2.5357   -0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904   -3.2358    0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6716   -2.0510    1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8753   -1.9479   -1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0901   -2.6448   -0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8432   -0.5721   -1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2016    1.8595   -0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3591    3.2255    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1843    2.2114    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2520   -0.4931   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726    2.6580    2.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0300    3.1668    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8374   -0.5201   -2.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1063    0.9580   -2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1627   -0.7398   -0.1522 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  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  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 20 23  2  0
 19 24  2  0
 10  2  1  0
 24 14  1  0
  9  4  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
 11 35  1  0
 15 36  1  0
 16 37  1  0
 21 38  1  0
 21 39  1  0
 24 40  1  0
M  END

808
  Mrv0541 02231215012D          

 24 26  0  0  1  0            999 V2000
    5.9484    2.7900    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0504    1.5619    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4742   -0.9608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8802    2.3692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2205    0.7546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -1.3010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.5169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8576    1.7320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -1.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -2.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1661   -1.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -0.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868    0.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2431    1.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6285    1.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6921    2.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8848    1.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  8  1  0  0  0  0
  2 21  1  0  0  0  0
  3 18  2  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 12  1  0  0  0  0
  7 18  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 17  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014946

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC2=CC=CC=C2N1NC(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16ClN3O3S/c1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23/h2-7,9-10H,8H2,1H3,(H,19,21)(H2,18,22,23)

> <INCHI_KEY>
NDDAHWYSQHTHNT-UHFFFAOYSA-N

> <FORMULA>
C16H16ClN3O3S

> <MOLECULAR_WEIGHT>
365.835

> <EXACT_MASS>
365.06008979

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.335191247745485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-chloro-N-(2-methyl-2,3-dihydro-1H-indol-1-yl)-3-sulfamoylbenzamide

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
2.6395443223333332

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.687086536864834

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.852269320760028

> <JCHEM_PKA_STRONGEST_BASIC>
0.09715835173557508

> <JCHEM_POLAR_SURFACE_AREA>
92.5

> <JCHEM_REFRACTIVITY>
103.3134

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indapamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014946
     RDKit          3D
Indapamide
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.1668   -2.9606    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -1.9066    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073   -1.8813   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8283   -0.4982   -0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0582    0.0402   -0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2387    1.3841   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277    2.1706   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9997    1.6198    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815    0.2703   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.5689    0.1441 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3143   -0.1750    0.1649 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2902    0.5782    1.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3861    0.9441    2.1678 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6897    0.9379    1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2297    2.0307    1.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5774    2.3008    1.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4130    1.4836    0.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1317    1.8436    0.7136 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8851    0.3914    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8799   -0.6546   -0.7269 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.6337    0.1312   -2.0485 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9726   -1.2843    0.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0657   -1.8161   -1.2669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5220    0.1308    0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7096   -3.8509   -0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -2.5357   -0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904   -3.2358    0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6716   -2.0510    1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8753   -1.9479   -1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0901   -2.6448   -0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8432   -0.5721   -1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2016    1.8595   -0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3591    3.2255    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1843    2.2114    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2520   -0.4931   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726    2.6580    2.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0300    3.1668    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8374   -0.5201   -2.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1063    0.9580   -2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1627   -0.7398   -0.1522 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  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  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 20 23  2  0
 19 24  2  0
 10  2  1  0
 24 14  1  0
  9  4  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
 11 35  1  0
 15 36  1  0
 16 37  1  0
 21 38  1  0
 21 39  1  0
 24 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 808                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      11.104   5.208   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      13.161   2.916   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      10.219  -1.793   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.843   4.423   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.478   1.409   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.205  -2.429   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.683  -0.965   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      14.668   3.233   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       8.103  -3.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.205  -4.907   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747  -4.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747  -2.898   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.643  -3.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -5.208   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -2.128   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -4.438   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -2.898   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.190  -0.647   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.668   0.816   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.175   1.134   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.654   2.598   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.640   1.963   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.625   3.744   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.118   3.426   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2    4    5    8   21                                             
CONECT    3   18                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    7    9   12                                                  
CONECT    7    6   18                                                       
CONECT    8    2                                                            
CONECT    9    6   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12    6   11   15                                                  
CONECT   13    9                                                            
CONECT   14   11   16                                                       
CONECT   15   12   17                                                       
CONECT   16   14   17                                                       
CONECT   17   15   16                                                       
CONECT   18    3    7   19                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21    2   20   23                                                  
CONECT   22   19   24                                                       
CONECT   23    1   21   24                                                  
CONECT   24   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0014946
HETATM    1  C1  UNL     1      -1.167  -2.961   0.003  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.210  -1.907   0.319  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.307  -1.881  -0.720  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.828  -0.498  -0.591  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.058   0.040  -0.896  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.239   1.384  -0.668  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.228   2.171  -0.153  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.000   1.620   0.149  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.781   0.270  -0.067  1.00  0.00           C  
HETATM   10  N1  UNL     1      -1.653  -0.569   0.144  1.00  0.00           N  
HETATM   11  N2  UNL     1      -0.314  -0.175   0.165  1.00  0.00           N  
HETATM   12  C10 UNL     1       0.290   0.578   1.187  1.00  0.00           C  
HETATM   13  O1  UNL     1      -0.386   0.944   2.168  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.690   0.938   1.114  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.230   2.031   1.748  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.577   2.301   1.624  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.413   1.484   0.864  1.00  0.00           C  
HETATM   18 CL1  UNL     1       6.132   1.844   0.714  1.00  0.00          CL  
HETATM   19  C15 UNL     1       3.885   0.391   0.229  1.00  0.00           C  
HETATM   20  S1  UNL     1       4.880  -0.655  -0.727  1.00  0.00           S  
HETATM   21  N3  UNL     1       5.634   0.131  -2.049  1.00  0.00           N  
HETATM   22  O2  UNL     1       5.973  -1.284   0.122  1.00  0.00           O  
HETATM   23  O3  UNL     1       4.066  -1.816  -1.267  1.00  0.00           O  
HETATM   24  C16 UNL     1       2.522   0.131   0.363  1.00  0.00           C  
HETATM   25  H1  UNL     1      -1.710  -3.851  -0.371  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.455  -2.536  -0.725  1.00  0.00           H  
HETATM   27  H3  UNL     1      -0.690  -3.236   0.955  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.672  -2.051   1.315  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.875  -1.948  -1.753  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.090  -2.645  -0.550  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.843  -0.572  -1.297  1.00  0.00           H  
HETATM   32  H8  UNL     1      -6.202   1.860  -0.895  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.359   3.225   0.029  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.184   2.211   0.553  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.252  -0.493  -0.684  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.573   2.658   2.333  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.030   3.167   2.120  1.00  0.00           H  
HETATM   38  H14 UNL     1       5.837  -0.520  -2.834  1.00  0.00           H  
HETATM   39  H15 UNL     1       5.106   0.958  -2.409  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.163  -0.740  -0.152  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   10   28
CONECT    3    4   29   30
CONECT    4    5    5    9
CONECT    5    6   31
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9    9   34
CONECT    9   10
CONECT   10   11
CONECT   11   12   35
CONECT   12   13   13   14
CONECT   14   15   15   24
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18   19
CONECT   19   20   24   24
CONECT   20   21   22   22   23
CONECT   20   23
CONECT   21   38   39
CONECT   24   40
END

HMDB0014946
     RDKit          3D
Indapamide
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.1668   -2.9606    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -1.9066    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073   -1.8813   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8283   -0.4982   -0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0582    0.0402   -0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2387    1.3841   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277    2.1706   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9997    1.6198    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815    0.2703   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.5689    0.1441 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3143   -0.1750    0.1649 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2902    0.5782    1.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3861    0.9441    2.1678 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6897    0.9379    1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2297    2.0307    1.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5774    2.3008    1.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4130    1.4836    0.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1317    1.8436    0.7136 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8851    0.3914    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8799   -0.6546   -0.7269 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.6337    0.1312   -2.0485 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9726   -1.2843    0.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0657   -1.8161   -1.2669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5220    0.1308    0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7096   -3.8509   -0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -2.5357   -0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904   -3.2358    0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6716   -2.0510    1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8753   -1.9479   -1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0901   -2.6448   -0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8432   -0.5721   -1.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2016    1.8595   -0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3591    3.2255    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1843    2.2114    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2520   -0.4931   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5726    2.6580    2.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0300    3.1668    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8374   -0.5201   -2.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1063    0.9580   -2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1627   -0.7398   -0.1522 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  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  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 20 23  2  0
 19 24  2  0
 10  2  1  0
 24 14  1  0
  9  4  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
 11 35  1  0
 15 36  1  0
 16 37  1  0
 21 38  1  0
 21 39  1  0
 24 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Indapamida	ChEBI
Indapamidum	ChEBI
Lozol	Kegg
Natrix	Kegg
Metindamide	HMDB

Chemical Formula

C₁₆H₁₆ClN₃O₃S

Average Molecular Weight

365.835

Monoisotopic Molecular Weight

365.06008979

IUPAC Name

4-chloro-N-(2-methyl-2,3-dihydro-1H-indol-1-yl)-3-sulfamoylbenzamide

Traditional Name

indapamide

CAS Registry Number

26807-65-8

SMILES

CC1CC2=CC=CC=C2N1NC(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O

InChI Identifier

InChI=1S/C16H16ClN3O3S/c1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23/h2-7,9-10H,8H2,1H3,(H,19,21)(H2,18,22,23)

InChI Key

NDDAHWYSQHTHNT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Halobenzoic acid or derivatives
4-halobenzoic acid or derivatives
Benzoic acid or derivatives
Benzenesulfonyl group
Indole or derivatives
Benzoyl
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Organosulfonic acid amide
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Carboxylic acid hydrazide
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Organosulfur compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:5893 )
organochlorine compound (CHEBI:5893 )
indoles (CHEBI:5893 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	161 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.034 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	185.6	30932474
[M+H]+	Not Available	184.63	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000804

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.034 g/L	ALOGPS
logP	2.52	ALOGPS
logP	2.64	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.85	ChemAxon
pKa (Strongest Basic)	0.097	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.5 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.31 m³·mol⁻¹	ChemAxon
Polarizability	36.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	177.615	30932474
DeepCCS	[M-H]-	175.257	30932474
DeepCCS	[M-2H]-	208.672	30932474
DeepCCS	[M+Na]+	183.899	30932474
AllCCS	[M+H]+	182.6	32859911
AllCCS	[M+H-H2O]+	179.6	32859911
AllCCS	[M+NH4]+	185.3	32859911
AllCCS	[M+Na]+	186.1	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	178.7	32859911
AllCCS	[M+HCOO]-	178.5	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.	5.73 minutes	32390414
Predicted by Siyang on May 30, 2022	13.5598 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.65 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2133.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	339.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	117.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	441.6 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	617.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	96.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1157.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	477.9 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	1383.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	287.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	199.5 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	61.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indapamide	CC1CC2=CC=CC=C2N1NC(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O	4491.3	Standard polar	33892256
Indapamide	CC1CC2=CC=CC=C2N1NC(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O	3415.0	Standard non polar	33892256
Indapamide	CC1CC2=CC=CC=C2N1NC(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O	3350.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indapamide,1TMS,isomer #1	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1	3206.4	Semi standard non polar	33892256
Indapamide,1TMS,isomer #1	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1	3172.0	Standard non polar	33892256
Indapamide,1TMS,isomer #1	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1	4145.5	Standard polar	33892256
Indapamide,1TMS,isomer #2	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C	3072.8	Semi standard non polar	33892256
Indapamide,1TMS,isomer #2	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C	3157.4	Standard non polar	33892256
Indapamide,1TMS,isomer #2	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C	4557.2	Standard polar	33892256
Indapamide,2TMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1)[Si](C)(C)C	3050.4	Semi standard non polar	33892256
Indapamide,2TMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1)[Si](C)(C)C	3271.8	Standard non polar	33892256
Indapamide,2TMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1)[Si](C)(C)C	3918.2	Standard polar	33892256
Indapamide,2TMS,isomer #2	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3174.8	Semi standard non polar	33892256
Indapamide,2TMS,isomer #2	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3345.7	Standard non polar	33892256
Indapamide,2TMS,isomer #2	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	4085.0	Standard polar	33892256
Indapamide,3TMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C	3050.7	Semi standard non polar	33892256
Indapamide,3TMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C	3457.1	Standard non polar	33892256
Indapamide,3TMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C	3858.3	Standard polar	33892256
Indapamide,1TBDMS,isomer #1	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1	3440.7	Semi standard non polar	33892256
Indapamide,1TBDMS,isomer #1	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1	3432.0	Standard non polar	33892256
Indapamide,1TBDMS,isomer #1	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1	4167.2	Standard polar	33892256
Indapamide,1TBDMS,isomer #2	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C(C)(C)C	3307.2	Semi standard non polar	33892256
Indapamide,1TBDMS,isomer #2	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C(C)(C)C	3392.6	Standard non polar	33892256
Indapamide,1TBDMS,isomer #2	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C(C)(C)C	4581.9	Standard polar	33892256
Indapamide,2TBDMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3446.7	Semi standard non polar	33892256
Indapamide,2TBDMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3778.9	Standard non polar	33892256
Indapamide,2TBDMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3975.2	Standard polar	33892256
Indapamide,2TBDMS,isomer #2	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3615.9	Semi standard non polar	33892256
Indapamide,2TBDMS,isomer #2	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3845.6	Standard non polar	33892256
Indapamide,2TBDMS,isomer #2	CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	4098.8	Standard polar	33892256
Indapamide,3TBDMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3650.0	Semi standard non polar	33892256
Indapamide,3TBDMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	4183.5	Standard non polar	33892256
Indapamide,3TBDMS,isomer #1	CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3934.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indapamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-4593000000-5ea2b9ed9ba04df04bf7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indapamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indapamide 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 - Indapamide LC-ESI-qTof , Positive-QTOF	splash10-001i-1900000000-861314def0ccc019ac04	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF	splash10-03di-0009000000-ed04e0a5871badc8b166	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF	splash10-03di-1729000000-15aecb441ef4febfe526	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF	splash10-000i-2910000000-b72aeba8db62ebdf9c17	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF	splash10-004r-6900000000-f819fedd1ac654d46dd4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF	splash10-004i-9300000000-164a2972880c967d2195	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF	splash10-004i-9100000000-d18afa355f919614b652	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF	splash10-01t9-9000000000-9d9e98925e9105738992	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF	splash10-03fr-9000000000-5e7568f4efd1730f47b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF	splash10-03di-9000000000-ecfffadaaa03b447eaf5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QTOF , positive-QTOF	splash10-001i-0904000000-530b78f6cae834e11768	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-235673a939e2e7d8c5e3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QTOF , positive-QTOF	splash10-0159-0900000000-a843660d42ffb01666fe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-cfee205b361c580e3631	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QTOF , positive-QTOF	splash10-00lr-0900000000-a6d8ff4d769ea09e8073	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , positive-QTOF	splash10-001i-0901000000-a76c5fd366807c180552	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-574a71dcc7f0b3f74693	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , positive-QTOF	splash10-001i-1900000000-ab046a8849c404d9b308	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , positive-QTOF	splash10-00l6-4900000000-93f1cc6465f329fd111e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indapamide 10V, Positive-QTOF	splash10-014i-0209000000-9154e3b65e4d452dacb3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indapamide 20V, Positive-QTOF	splash10-00ls-0968000000-bfc678a87120a2f04f23	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indapamide 40V, Positive-QTOF	splash10-014i-0920000000-26f53b22345a5ccf8302	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indapamide 10V, Negative-QTOF	splash10-03di-1119000000-10d511f58b646ce4b134	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indapamide 20V, Negative-QTOF	splash10-01t9-9558000000-8fe9e9ce749aec787743	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indapamide 40V, Negative-QTOF	splash10-004i-9210000000-6029683889b96e37eacb	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Indapamide 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 DB00808	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00808	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00808

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3574

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Indapamide

METLIN ID

Not Available

PubChem Compound

3702

PDB ID

Not Available

ChEBI ID

5893

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

Dong DL, Wang QH, Yue P, Jiao JD, Gu RM, Yang BF: Indapamide induces apoptosis of GH3 pituitary cells independently of its inhibition of voltage-dependent K+ currents. Eur J Pharmacol. 2006 Apr 24;536(1-2):78-84. Epub 2006 Mar 2. [PubMed:16556441 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Sun H, Moore C, Dansette PM, Kumar S, Halpert JR, Yost GS: Dehydrogenation of the indoline-containing drug 4-chloro-N-(2-methyl-1-indolinyl)-3-sulfamoylbenzamide (indapamide) by CYP3A4: correlation with in silico predictions. Drug Metab Dispos. 2009 Mar;37(3):672-84. doi: 10.1124/dmd.108.022707. Epub 2008 Dec 12. [PubMed:19074530 ]

Enzyme Details

2. Potassium voltage-gated channel subfamily KQT member 1

General function:: Involved in ion channel activity
Specific function:: Probably important in cardiac repolarization. Associates with KCNE1 (MinK) to form the I(Ks) cardiac potassium current. Elicits a rapidly activating, potassium-selective outward current. Muscarinic agonist oxotremorine-M strongly suppresses KCNQ1/KCNE1 current in CHO cells in which cloned KCNQ1/KCNE1 channels were coexpressed with M1 muscarinic receptors. May associate also with KCNE3 (MiRP2) to form the potassium channel that is important for cyclic AMP-stimulated intestinal secretion of chloride ions, which is reduced in cystic fibrosis and pathologically stimulated in cholera and other forms of secretory diarrhea
Gene Name:: KCNQ1
Uniprot ID:: P51787
Molecular weight:: 74697.9

References

Ohya S, Asakura K, Muraki K, Watanabe M, Imaizumi Y: Molecular and functional characterization of ERG, KCNQ, and KCNE subtypes in rat stomach smooth muscle. Am J Physiol Gastrointest Liver Physiol. 2002 Feb;282(2):G277-87. [PubMed:11804849 ]
Li RA, Miake J, Hoppe UC, Johns DC, Marban E, Nuss HB: Functional consequences of the arrhythmogenic G306R KvLQT1 K+ channel mutant probed by viral gene transfer in cardiomyocytes. J Physiol. 2001 May 15;533(Pt 1):127-33. [PubMed:11351021 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Potassium voltage-gated channel subfamily E member 1

General function:: Involved in voltage-gated potassium channel activity
Specific function:: Ancillary protein that assembles as a beta subunit with a voltage-gated potassium channel complex of pore-forming alpha subunits. Modulates the gating kinetics and enhances stability of the channel complex. Assembled with KCNQ1/KVLQT1 is proposed to form the slowly activating delayed rectifier cardiac potassium (IKs) channel. The outward current reaches its steady state only after 50 seconds. Assembled with KCNH2/HERG may modulate the rapidly activating component of the delayed rectifying potassium current in heart (IKr)
Gene Name:: KCNE1
Uniprot ID:: P15382
Molecular weight:: 14674.7

References

Ohya S, Asakura K, Muraki K, Watanabe M, Imaizumi Y: Molecular and functional characterization of ERG, KCNQ, and KCNE subtypes in rat stomach smooth muscle. Am J Physiol Gastrointest Liver Physiol. 2002 Feb;282(2):G277-87. [PubMed:11804849 ]

Showing metabocard for Indapamide (HMDB0014946)

MOL for HMDB0014946 (Indapamide)

3D MOL for HMDB0014946 (Indapamide)

3D SDF for HMDB0014946 (Indapamide)

3D-SDF for HMDB0014946 (Indapamide)

PDB for HMDB0014946 (Indapamide)

3D PDB for HMDB0014946 (Indapamide)

SMILES for HMDB0014946 (Indapamide)

INCHI for HMDB0014946 (Indapamide)

Structure for HMDB0014946 (Indapamide)

3D Structure for HMDB0014946 (Indapamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References