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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:07:00 UTC

Update Date

2021-09-26 23:12:22 UTC

HMDB ID

HMDB0256593

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Piretanide

Description

Piretanide, also known as arelix, belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. Based on a literature review very few articles have been published on Piretanide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Piretanide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Piretanide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0256593
     RDKit          3D
Piretanide
 43 45  0  0  0  0  0  0  0  0999 V2000
    2.0074    2.7701   -2.3026 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0290    2.7750   -0.5654 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1268    1.9479   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2072    4.1778   -0.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4796    2.1818    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3061    3.0050    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186    2.5938    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3107    3.4648    2.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198    3.0954    2.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8693    4.7389    2.5182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696    1.3282    1.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1845    0.5115    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7218   -0.7879   -0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0430   -1.3417   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846   -2.8364   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7222   -2.8842    0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162   -1.7368    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240    0.9254   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685    0.1030   -1.0446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146   -0.7998   -0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510   -1.5283   -1.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3246   -2.4682   -1.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6991   -2.7187   -0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0752   -2.0024    0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054   -1.0670    0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283    2.1842   -2.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9438    3.7487   -2.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0772    3.9888    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3764    4.9612    3.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9271    0.9715    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0062   -1.0090   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2207   -1.1117   -2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395   -3.3625   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -3.2827   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500   -3.8545    0.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8102   -2.6665    0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -1.3003    1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -2.1317    1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0772   -1.3551   -2.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8066   -3.0245   -2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610   -3.4579    0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986   -2.2281    1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6283   -0.5170    1.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  5  1  0
 25 20  1  0
 17 13  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 24 42  1  0
 25 43  1  0
M  END


  Mrv0541 02231216332D          

 25 27  0  0  0  0            999 V2000
    3.4656    0.3509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -0.7761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.6529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -2.5366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6548   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    0.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
  9 15  2  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256593

> <DATABASE_NAME>
hmdb

> <SMILES>
NS(=O)(=O)C1=CC(=CC(N2CCCC2)=C1OC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H18N2O5S/c18-25(22,23)15-11-12(17(20)21)10-14(19-8-4-5-9-19)16(15)24-13-6-2-1-3-7-13/h1-3,6-7,10-11H,4-5,8-9H2,(H,20,21)(H2,18,22,23)

> <INCHI_KEY>
UJEWTUDSLQGTOA-UHFFFAOYSA-N

> <FORMULA>
C17H18N2O5S

> <MOLECULAR_WEIGHT>
362.4

> <EXACT_MASS>
362.093642386

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.847205273350674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acid

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.2509880019999997

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.613149397040196

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.67541364054576

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6197086963948472

> <JCHEM_POLAR_SURFACE_AREA>
109.93

> <JCHEM_REFRACTIVITY>
93.68250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
piretanide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256593
     RDKit          3D
Piretanide
 43 45  0  0  0  0  0  0  0  0999 V2000
    2.0074    2.7701   -2.3026 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0290    2.7750   -0.5654 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1268    1.9479   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2072    4.1778   -0.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4796    2.1818    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3061    3.0050    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186    2.5938    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3107    3.4648    2.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198    3.0954    2.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8693    4.7389    2.5182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696    1.3282    1.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1845    0.5115    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7218   -0.7879   -0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0430   -1.3417   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846   -2.8364   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7222   -2.8842    0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162   -1.7368    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240    0.9254   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685    0.1030   -1.0446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146   -0.7998   -0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510   -1.5283   -1.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3246   -2.4682   -1.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6991   -2.7187   -0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0752   -2.0024    0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054   -1.0670    0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283    2.1842   -2.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9438    3.7487   -2.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0772    3.9888    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3764    4.9612    3.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9271    0.9715    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0062   -1.0090   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2207   -1.1117   -2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395   -3.3625   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -3.2827   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500   -3.8545    0.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8102   -2.6665    0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -1.3003    1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -2.1317    1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0772   -1.3551   -2.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8066   -3.0245   -2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610   -3.4579    0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986   -2.2281    1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6283   -0.5170    1.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  5  1  0
 25 20  1  0
 17 13  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 24 42  1  0
 25 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       6.469   0.655   0.000  0.00  0.00           N+0
HETATM    2  S   UNK     0       5.136  -0.115   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       5.906  -1.449   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.366   1.219   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.468  -0.115   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.135  -0.885   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.135  -2.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.468  -3.195   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.468  -4.735   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.714  -5.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.238  -7.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.698  -7.105   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.222  -5.640   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.136  -3.195   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.469  -2.425   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.469  -0.885   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.803  -0.115   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.137  -0.885   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.137  -2.425   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.803  -3.195   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.199  -0.115   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.199   1.425   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.533  -0.885   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15    9    5   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23    7   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0256593
HETATM    1  N1  UNL     1       2.007   2.770  -2.303  1.00  0.00           N  
HETATM    2  S1  UNL     1       2.029   2.775  -0.565  1.00  0.00           S  
HETATM    3  O1  UNL     1       3.127   1.948  -0.008  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.207   4.178  -0.117  1.00  0.00           O  
HETATM    5  C1  UNL     1       0.480   2.182   0.047  1.00  0.00           C  
HETATM    6  C2  UNL     1      -0.306   3.005   0.860  1.00  0.00           C  
HETATM    7  C3  UNL     1      -1.519   2.594   1.361  1.00  0.00           C  
HETATM    8  C4  UNL     1      -2.311   3.465   2.198  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.420   3.095   2.660  1.00  0.00           O  
HETATM   10  O4  UNL     1      -1.869   4.739   2.518  1.00  0.00           O  
HETATM   11  C5  UNL     1      -1.970   1.328   1.051  1.00  0.00           C  
HETATM   12  C6  UNL     1      -1.184   0.511   0.242  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.722  -0.788  -0.035  1.00  0.00           N  
HETATM   14  C7  UNL     1      -2.043  -1.342  -1.336  1.00  0.00           C  
HETATM   15  C8  UNL     1      -2.085  -2.836  -1.057  1.00  0.00           C  
HETATM   16  C9  UNL     1      -2.722  -2.884   0.314  1.00  0.00           C  
HETATM   17  C10 UNL     1      -2.016  -1.737   1.022  1.00  0.00           C  
HETATM   18  C11 UNL     1       0.024   0.925  -0.256  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.768   0.103  -1.045  1.00  0.00           O  
HETATM   20  C12 UNL     1       1.715  -0.800  -0.652  1.00  0.00           C  
HETATM   21  C13 UNL     1       2.351  -1.528  -1.663  1.00  0.00           C  
HETATM   22  C14 UNL     1       3.325  -2.468  -1.371  1.00  0.00           C  
HETATM   23  C15 UNL     1       3.699  -2.719  -0.089  1.00  0.00           C  
HETATM   24  C16 UNL     1       3.075  -2.002   0.925  1.00  0.00           C  
HETATM   25  C17 UNL     1       2.105  -1.067   0.626  1.00  0.00           C  
HETATM   26  H1  UNL     1       1.228   2.184  -2.668  1.00  0.00           H  
HETATM   27  H2  UNL     1       1.944   3.749  -2.683  1.00  0.00           H  
HETATM   28  H3  UNL     1       0.077   3.989   1.082  1.00  0.00           H  
HETATM   29  H4  UNL     1      -1.376   4.961   3.371  1.00  0.00           H  
HETATM   30  H5  UNL     1      -2.927   0.971   1.433  1.00  0.00           H  
HETATM   31  H6  UNL     1      -3.006  -1.009  -1.731  1.00  0.00           H  
HETATM   32  H7  UNL     1      -1.221  -1.112  -2.075  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.740  -3.362  -1.806  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.070  -3.283  -1.013  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.550  -3.855   0.822  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.810  -2.667   0.173  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.628  -1.300   1.829  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.039  -2.132   1.369  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.077  -1.355  -2.705  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.807  -3.025  -2.185  1.00  0.00           H  
HETATM   41  H16 UNL     1       4.461  -3.458   0.102  1.00  0.00           H  
HETATM   42  H17 UNL     1       3.399  -2.228   1.934  1.00  0.00           H  
HETATM   43  H18 UNL     1       1.628  -0.517   1.424  1.00  0.00           H  
CONECT    1    2   26   27
CONECT    2    3    3    4    4
CONECT    2    5
CONECT    5    6    6   18
CONECT    6    7   28
CONECT    7    8   11   11
CONECT    8    9    9   10
CONECT   10   29
CONECT   11   12   30
CONECT   12   13   18   18
CONECT   13   14   17
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   35   36
CONECT   17   37   38
CONECT   18   19
CONECT   19   20
CONECT   20   21   21   25
CONECT   21   22   39
CONECT   22   23   23   40
CONECT   23   24   41
CONECT   24   25   25   42
CONECT   25   43
END

HMDB0256593
     RDKit          3D
Piretanide
 43 45  0  0  0  0  0  0  0  0999 V2000
    2.0074    2.7701   -2.3026 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0290    2.7750   -0.5654 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1268    1.9479   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2072    4.1778   -0.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4796    2.1818    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3061    3.0050    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186    2.5938    1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3107    3.4648    2.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198    3.0954    2.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8693    4.7389    2.5182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696    1.3282    1.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1845    0.5115    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7218   -0.7879   -0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0430   -1.3417   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846   -2.8364   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7222   -2.8842    0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162   -1.7368    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240    0.9254   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685    0.1030   -1.0446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146   -0.7998   -0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3510   -1.5283   -1.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3246   -2.4682   -1.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6991   -2.7187   -0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0752   -2.0024    0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054   -1.0670    0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283    2.1842   -2.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9438    3.7487   -2.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0772    3.9888    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3764    4.9612    3.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9271    0.9715    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0062   -1.0090   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2207   -1.1117   -2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395   -3.3625   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -3.2827   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5500   -3.8545    0.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8102   -2.6665    0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -1.3003    1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -2.1317    1.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0772   -1.3551   -2.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8066   -3.0245   -2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610   -3.4579    0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986   -2.2281    1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6283   -0.5170    1.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  5  1  0
 25 20  1  0
 17 13  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 24 42  1  0
 25 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Arelix	Kegg
4-Phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid	MeSH
HOE 118	MeSH

Chemical Formula

C₁₇H₁₈N₂O₅S

Average Molecular Weight

362.4

Monoisotopic Molecular Weight

362.093642386

IUPAC Name

4-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acid

Traditional Name

piretanide

CAS Registry Number

Not Available

SMILES

NS(=O)(=O)C1=CC(=CC(N2CCCC2)=C1OC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C17H18N2O5S/c18-25(22,23)15-11-12(17(20)21)10-14(19-8-4-5-9-19)16(15)24-13-6-2-1-3-7-13/h1-3,6-7,10-11H,4-5,8-9H2,(H,20,21)(H2,18,22,23)

InChI Key

UJEWTUDSLQGTOA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
Aminobenzenesulfonamide
1-phenylpyrrolidine
Diaryl ether
Aminobenzoic acid
Aminobenzoic acid or derivatives
Benzenesulfonamide
Benzoic acid
Benzoic acid or derivatives
Benzenesulfonyl group
Tertiary aliphatic/aromatic amine
Benzoyl
Aniline or substituted anilines
Dialkylarylamine
Phenol ether
Phenoxy compound
Organosulfonic acid amide
Aminosulfonyl compound
Pyrrole
Pyrrolidine
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Amino acid or derivatives
Tertiary amine
Amino acid
Azacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organosulfur compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.2	ALOGPS
logP	2.25	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-0.62	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.93 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.68 m³·mol⁻¹	ChemAxon
Polarizability	35.85 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]+	176.081	30932474
DeepCCS	[M-H]-	173.723	30932474
DeepCCS	[M-2H]-	207.593	30932474
DeepCCS	[M+Na]+	182.82	30932474
AllCCS	[M+H]+	180.9	32859911
AllCCS	[M+H-H2O]+	178.1	32859911
AllCCS	[M+NH4]+	183.6	32859911
AllCCS	[M+Na]+	184.3	32859911
AllCCS	[M-H]-	177.8	32859911
AllCCS	[M+Na-2H]-	177.6	32859911
AllCCS	[M+HCOO]-	177.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piretanide	NS(=O)(=O)C1=CC(=CC(N2CCCC2)=C1OC1=CC=CC=C1)C(O)=O	4654.4	Standard polar	33892256
Piretanide	NS(=O)(=O)C1=CC(=CC(N2CCCC2)=C1OC1=CC=CC=C1)C(O)=O	3133.8	Standard non polar	33892256
Piretanide	NS(=O)(=O)C1=CC(=CC(N2CCCC2)=C1OC1=CC=CC=C1)C(O)=O	3453.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piretanide,2TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC(C(=O)O[Si](C)(C)C)=CC(N2CCCC2)=C1OC1=CC=CC=C1	3253.3	Semi standard non polar	33892256
Piretanide,2TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC(C(=O)O[Si](C)(C)C)=CC(N2CCCC2)=C1OC1=CC=CC=C1	3284.9	Standard non polar	33892256
Piretanide,2TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC(C(=O)O[Si](C)(C)C)=CC(N2CCCC2)=C1OC1=CC=CC=C1	4158.2	Standard polar	33892256
Piretanide,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC(C(=O)O)=CC(N2CCCC2)=C1OC1=CC=CC=C1	3260.9	Semi standard non polar	33892256
Piretanide,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC(C(=O)O)=CC(N2CCCC2)=C1OC1=CC=CC=C1	3376.9	Standard non polar	33892256
Piretanide,2TMS,isomer #2	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC(C(=O)O)=CC(N2CCCC2)=C1OC1=CC=CC=C1	4277.4	Standard polar	33892256
Piretanide,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N2CCCC2)=C(OC2=CC=CC=C2)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3271.2	Semi standard non polar	33892256
Piretanide,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N2CCCC2)=C(OC2=CC=CC=C2)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	3431.5	Standard non polar	33892256
Piretanide,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N2CCCC2)=C(OC2=CC=CC=C2)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	4093.0	Standard polar	33892256
Piretanide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(N2CCCC2)=C1OC1=CC=CC=C1	3666.6	Semi standard non polar	33892256
Piretanide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(N2CCCC2)=C1OC1=CC=CC=C1	3811.7	Standard non polar	33892256
Piretanide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(N2CCCC2)=C1OC1=CC=CC=C1	4234.1	Standard polar	33892256
Piretanide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC(C(=O)O)=CC(N2CCCC2)=C1OC1=CC=CC=C1	3731.2	Semi standard non polar	33892256
Piretanide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC(C(=O)O)=CC(N2CCCC2)=C1OC1=CC=CC=C1	3877.1	Standard non polar	33892256
Piretanide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC(C(=O)O)=CC(N2CCCC2)=C1OC1=CC=CC=C1	4301.4	Standard polar	33892256
Piretanide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N2CCCC2)=C(OC2=CC=CC=C2)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3885.5	Semi standard non polar	33892256
Piretanide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N2CCCC2)=C(OC2=CC=CC=C2)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	4185.4	Standard non polar	33892256
Piretanide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N2CCCC2)=C(OC2=CC=CC=C2)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	4178.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Piretanide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001m-4194000000-625e0ba14afa2ffee540	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piretanide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piretanide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piretanide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piretanide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piretanide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piretanide LC-ESI-qTof , Positive-QTOF	splash10-000i-3980000000-dc67e28bf67c9f799108	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piretanide , positive-QTOF	splash10-000i-3980000000-dc67e28bf67c9f799108	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piretanide 10V, Positive-QTOF	splash10-03di-0019000000-ff0f88ecfe2c8603f592	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piretanide 20V, Positive-QTOF	splash10-014i-0179000000-33b14175fb0ca1b8c527	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piretanide 40V, Positive-QTOF	splash10-03di-1390000000-ee1de56f2481858b2ae4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piretanide 10V, Negative-QTOF	splash10-03di-4009000000-a02bb82a138376f82b62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piretanide 20V, Negative-QTOF	splash10-02vj-6459000000-4a209e12057a0ff1f04e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piretanide 40V, Negative-QTOF	splash10-004l-9110000000-c0696e29ff54a56554ef	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02925

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4683

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piretanide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Piretanide (HMDB0256593)

MOL for HMDB0256593 (Piretanide)

3D MOL for HMDB0256593 (Piretanide)

3D SDF for HMDB0256593 (Piretanide)

3D-SDF for HMDB0256593 (Piretanide)

PDB for HMDB0256593 (Piretanide)

3D PDB for HMDB0256593 (Piretanide)

SMILES for HMDB0256593 (Piretanide)

INCHI for HMDB0256593 (Piretanide)

Structure for HMDB0256593 (Piretanide)

3D Structure for HMDB0256593 (Piretanide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra