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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 02:51:42 UTC

HMDB ID

HMDB0014702

Secondary Accession Numbers

HMDB14702

Metabolite Identification

Common Name

Benzthiazide

Description

Benzthiazide is used to treat hypertension and edema. Like other thiazides, benzthiazide promotes water loss from the body (diuretics). They inhibit Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys. Thiazides also cause loss of potassium and an increase in serum uric acid. Thiazides are often used to treat hypertension, but their hypotensive effects are not necessarily due to their diuretic activity. Thiazides have been shown to prevent hypertension-related morbidity and mortality although the mechanism is not fully understood. Thiazides cause vasodilation by activating calcium-activated potassium channels (large conductance) in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue.

Structure

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

562
  Mrv0541 02231214462D          

 26 28  0  0  0  0            999 V2000
    9.5636    1.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.6074    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5636   -0.6273    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6301    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.3219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.3219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9789    0.0856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1484   -1.3402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    1.0426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -0.1949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2765   -1.0426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658   -0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658    0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1032   -0.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8508   -0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1032    1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8508    0.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  2  0  0  0  0
  2 10  1  0  0  0  0
  2 12  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  2  0  0  0  0
  3 11  1  0  0  0  0
  3 15  1  0  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  9 13  1  0  0  0  0
  9 16  1  0  0  0  0
 10 16  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 17  2  0  0  0  0
 14 15  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0014702
     RDKit          3D
Benzthiazide
 40 42  0  0  0  0  0  0  0  0999 V2000
    6.2938    1.2477   -1.5890 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991   -0.4019   -1.2396 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.1385   -1.2220   -2.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0933   -0.8863   -0.3341 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4103   -0.6421   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5480    0.4083   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2971    0.2558    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233   -0.9743    0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975   -2.0495    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9491   -1.8880   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0330   -3.2396   -0.4426 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -1.2056    1.1705 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -0.1949    1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -0.5603    2.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975    0.9625    2.3156 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    1.6688    0.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0414    0.7577    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4043    0.9926    0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2955    0.1557   -0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8769   -0.8973   -1.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5101   -1.1322   -1.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6025   -0.2857   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934    1.0398    1.1708 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530    1.6513    0.4764 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.9037    2.6310    1.4285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9165    2.3140   -0.8427 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5722    1.3401   -2.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9019    1.7074   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8925    1.3973   -0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -3.0275    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618   -2.1850    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -1.0285    3.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2646   -1.2728    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497    2.6724    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1662    1.7820    0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7226    1.8067    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3537    0.3150   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5759   -1.5548   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1714   -1.9566   -1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5548   -0.4504   -0.8760 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 13 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  2  0
 10  5  1  0
 22 17  1  0
 24  7  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  9 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

562
  Mrv0541 02231214462D          

 26 28  0  0  0  0            999 V2000
    9.5636    1.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.6074    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5636   -0.6273    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6301    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.3219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.3219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9789    0.0856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1484   -1.3402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    1.0426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -0.1949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2765   -1.0426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658   -0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658    0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1032   -0.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8508   -0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1032    1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8508    0.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  2  0  0  0  0
  2 10  1  0  0  0  0
  2 12  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  2  0  0  0  0
  3 11  1  0  0  0  0
  3 15  1  0  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  9 13  1  0  0  0  0
  9 16  1  0  0  0  0
 10 16  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 17  2  0  0  0  0
 14 15  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014702

> <DATABASE_NAME>
hmdb

> <SMILES>
NS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14ClN3O4S3/c16-11-6-12-14(7-13(11)25(17,20)21)26(22,23)19-15(18-12)9-24-8-10-4-2-1-3-5-10/h1-7H,8-9H2,(H,18,19)(H2,17,20,21)

> <INCHI_KEY>
NDTSRXAMMQDVSW-UHFFFAOYSA-N

> <FORMULA>
C15H14ClN3O4S3

> <MOLECULAR_WEIGHT>
431.937

> <EXACT_MASS>
430.983495728

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
41.497834142841306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-4H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
1.8407870076666661

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.331303545721813

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.766787375197374

> <JCHEM_PKA_STRONGEST_BASIC>
1.2487234919688748

> <JCHEM_POLAR_SURFACE_AREA>
118.69

> <JCHEM_REFRACTIVITY>
104.14070000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
regulon

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014702
     RDKit          3D
Benzthiazide
 40 42  0  0  0  0  0  0  0  0999 V2000
    6.2938    1.2477   -1.5890 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991   -0.4019   -1.2396 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.1385   -1.2220   -2.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0933   -0.8863   -0.3341 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4103   -0.6421   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5480    0.4083   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2971    0.2558    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233   -0.9743    0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975   -2.0495    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9491   -1.8880   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0330   -3.2396   -0.4426 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -1.2056    1.1705 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -0.1949    1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -0.5603    2.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975    0.9625    2.3156 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    1.6688    0.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0414    0.7577    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4043    0.9926    0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2955    0.1557   -0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8769   -0.8973   -1.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5101   -1.1322   -1.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6025   -0.2857   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934    1.0398    1.1708 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530    1.6513    0.4764 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.9037    2.6310    1.4285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9165    2.3140   -0.8427 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5722    1.3401   -2.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9019    1.7074   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8925    1.3973   -0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -3.0275    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618   -2.1850    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -1.0285    3.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2646   -1.2728    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497    2.6724    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1662    1.7820    0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7226    1.8067    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3537    0.3150   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5759   -1.5548   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1714   -1.9566   -1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5548   -0.4504   -0.8760 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 13 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  2  0
 10  5  1  0
 22 17  1  0
 24  7  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  9 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 562                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      17.852   1.983   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      12.416  -1.134   0.000  0.00  0.00           S+0
HETATM    3  S   UNK     0      17.852  -1.171   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0       8.415   1.176   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0      13.186  -2.468   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      11.646  -2.468   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.627   0.160   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      17.077  -2.502   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      12.416   1.946   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      11.082  -0.364   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      19.183  -1.946   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      13.749  -0.364   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.749   1.176   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.126  -1.187   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.521  -0.396   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082   1.176   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.126   2.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.521   1.208   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748   1.946   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081   1.946   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.747   1.176   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.747  -0.364   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414   1.946   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414  -1.134   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080   1.176   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080  -0.364   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2    5    6   10   12                                             
CONECT    3    7    8   11   15                                             
CONECT    4   19   20                                                       
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
CONECT    8    3                                                            
CONECT    9   13   16                                                       
CONECT   10    2   16                                                       
CONECT   11    3                                                            
CONECT   12    2   13   14                                                  
CONECT   13    9   12   17                                                  
CONECT   14   12   15                                                       
CONECT   15    3   14   18                                                  
CONECT   16    9   10   19                                                  
CONECT   17   13   18                                                       
CONECT   18    1   15   17                                                  
CONECT   19    4   16                                                       
CONECT   20    4   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   26                                                       
CONECT   26   24   25                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0014702
HETATM    1  N1  UNL     1       6.294   1.248  -1.589  1.00  0.00           N  
HETATM    2  S1  UNL     1       5.999  -0.402  -1.240  1.00  0.00           S  
HETATM    3  O1  UNL     1       6.138  -1.222  -2.516  1.00  0.00           O  
HETATM    4  O2  UNL     1       7.093  -0.886  -0.334  1.00  0.00           O  
HETATM    5  C1  UNL     1       4.410  -0.642  -0.539  1.00  0.00           C  
HETATM    6  C2  UNL     1       3.548   0.408  -0.320  1.00  0.00           C  
HETATM    7  C3  UNL     1       2.297   0.256   0.228  1.00  0.00           C  
HETATM    8  C4  UNL     1       1.823  -0.974   0.597  1.00  0.00           C  
HETATM    9  C5  UNL     1       2.697  -2.050   0.377  1.00  0.00           C  
HETATM   10  C6  UNL     1       3.949  -1.888  -0.173  1.00  0.00           C  
HETATM   11 CL1  UNL     1       5.033  -3.240  -0.443  1.00  0.00          CL  
HETATM   12  N2  UNL     1       0.539  -1.206   1.171  1.00  0.00           N  
HETATM   13  C7  UNL     1      -0.419  -0.195   1.435  1.00  0.00           C  
HETATM   14  C8  UNL     1      -1.755  -0.560   2.049  1.00  0.00           C  
HETATM   15  S2  UNL     1      -2.697   0.963   2.316  1.00  0.00           S  
HETATM   16  C9  UNL     1      -3.093   1.669   0.694  1.00  0.00           C  
HETATM   17  C10 UNL     1      -4.041   0.758   0.029  1.00  0.00           C  
HETATM   18  C11 UNL     1      -5.404   0.993   0.216  1.00  0.00           C  
HETATM   19  C12 UNL     1      -6.296   0.156  -0.389  1.00  0.00           C  
HETATM   20  C13 UNL     1      -5.877  -0.897  -1.168  1.00  0.00           C  
HETATM   21  C14 UNL     1      -4.510  -1.132  -1.356  1.00  0.00           C  
HETATM   22  C15 UNL     1      -3.603  -0.286  -0.744  1.00  0.00           C  
HETATM   23  N3  UNL     1      -0.193   1.040   1.171  1.00  0.00           N  
HETATM   24  S3  UNL     1       1.253   1.651   0.476  1.00  0.00           S  
HETATM   25  O3  UNL     1       1.904   2.631   1.428  1.00  0.00           O  
HETATM   26  O4  UNL     1       0.916   2.314  -0.843  1.00  0.00           O  
HETATM   27  H1  UNL     1       6.572   1.340  -2.571  1.00  0.00           H  
HETATM   28  H2  UNL     1       6.902   1.707  -0.905  1.00  0.00           H  
HETATM   29  H3  UNL     1       3.892   1.397  -0.602  1.00  0.00           H  
HETATM   30  H4  UNL     1       2.340  -3.027   0.663  1.00  0.00           H  
HETATM   31  H5  UNL     1       0.262  -2.185   1.421  1.00  0.00           H  
HETATM   32  H6  UNL     1      -1.616  -1.029   3.045  1.00  0.00           H  
HETATM   33  H7  UNL     1      -2.265  -1.273   1.403  1.00  0.00           H  
HETATM   34  H8  UNL     1      -3.550   2.672   0.865  1.00  0.00           H  
HETATM   35  H9  UNL     1      -2.166   1.782   0.073  1.00  0.00           H  
HETATM   36  H10 UNL     1      -5.723   1.807   0.818  1.00  0.00           H  
HETATM   37  H11 UNL     1      -7.354   0.315  -0.261  1.00  0.00           H  
HETATM   38  H12 UNL     1      -6.576  -1.555  -1.644  1.00  0.00           H  
HETATM   39  H13 UNL     1      -4.171  -1.957  -1.966  1.00  0.00           H  
HETATM   40  H14 UNL     1      -2.555  -0.450  -0.876  1.00  0.00           H  
CONECT    1    2   27   28
CONECT    2    3    3    4    4
CONECT    2    5
CONECT    5    6    6   10
CONECT    6    7   29
CONECT    7    8    8   24
CONECT    8    9   12
CONECT    9   10   10   30
CONECT   10   11
CONECT   12   13   31
CONECT   13   14   23   23
CONECT   14   15   32   33
CONECT   15   16
CONECT   16   17   34   35
CONECT   17   18   18   22
CONECT   18   19   36
CONECT   19   20   20   37
CONECT   20   21   38
CONECT   21   22   22   39
CONECT   22   40
CONECT   23   24
CONECT   24   25   25   26   26
END

HMDB0014702
     RDKit          3D
Benzthiazide
 40 42  0  0  0  0  0  0  0  0999 V2000
    6.2938    1.2477   -1.5890 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991   -0.4019   -1.2396 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.1385   -1.2220   -2.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0933   -0.8863   -0.3341 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4103   -0.6421   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5480    0.4083   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2971    0.2558    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233   -0.9743    0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975   -2.0495    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9491   -1.8880   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0330   -3.2396   -0.4426 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -1.2056    1.1705 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -0.1949    1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -0.5603    2.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975    0.9625    2.3156 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927    1.6688    0.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0414    0.7577    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4043    0.9926    0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2955    0.1557   -0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8769   -0.8973   -1.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5101   -1.1322   -1.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6025   -0.2857   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934    1.0398    1.1708 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530    1.6513    0.4764 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.9037    2.6310    1.4285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9165    2.3140   -0.8427 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5722    1.3401   -2.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9019    1.7074   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8925    1.3973   -0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -3.0275    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618   -2.1850    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -1.0285    3.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2646   -1.2728    1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5497    2.6724    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1662    1.7820    0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7226    1.8067    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3537    0.3150   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5759   -1.5548   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1714   -1.9566   -1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5548   -0.4504   -0.8760 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 13 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  2  0
 10  5  1  0
 22 17  1  0
 24  7  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  9 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-((Benzylthio)methyl)-6-chloro-7-sulfamoyl-2H-benzo-1,2,4-thiadiazine 1,1-dioxide	ChEBI
3-Benzylthiomethyl-6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide	ChEBI
3-Benzylthiomethyl-6-chloro-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide	ChEBI
6-Chloro-1,1-dioxo-3-(phenylmethylsulfanylmethyl)-4H-benzo[e][1,2,4]thiadiazine-7-sulfonamide	ChEBI
6-Chloro-7-sulfamoyl-3-benzylthiomethyl-2H-1,2,4-benzothiadiazine 1,1-dioxide	ChEBI
Benzothiazide	ChEBI
Benzotiazida	ChEBI
Benzthiazidum	ChEBI
Exna	Kegg
3-((Benzylthio)methyl)-6-chloro-7-sulphamoyl-2H-benzo-1,2,4-thiadiazine 1,1-dioxide	Generator
3-Benzylthiomethyl-6-chloro-2H-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxide	Generator
3-Benzylthiomethyl-6-chloro-7-sulphamoyl-1,2,4-benzothiadiazine 1,1-dioxide	Generator
6-Chloro-1,1-dioxo-3-(phenylmethylsulphanylmethyl)-4H-benzo[e][1,2,4]thiadiazine-7-sulphonamide	Generator
6-Chloro-7-sulphamoyl-3-benzylthiomethyl-2H-1,2,4-benzothiadiazine 1,1-dioxide	Generator

Chemical Formula

C₁₅H₁₄ClN₃O₄S₃

Average Molecular Weight

431.937

Monoisotopic Molecular Weight

430.983495728

IUPAC Name

3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-4H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide

Traditional Name

regulon

CAS Registry Number

91-33-8

SMILES

NS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C1

InChI Identifier

InChI=1S/C15H14ClN3O4S3/c16-11-6-12-14(7-13(11)25(17,20)21)26(22,23)19-15(18-12)9-24-8-10-4-2-1-3-5-10/h1-7H,8-9H2,(H,18,19)(H2,17,20,21)

InChI Key

NDTSRXAMMQDVSW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2,4-benzothiadiazine-1,1-dioxides. These are aromatic heterocyclic compounds containing a 1,2,4-benzothiadiazine ring system with two S=O bonds at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thiadiazines

Sub Class

Benzothiadiazines

Direct Parent

1,2,4-benzothiadiazine-1,1-dioxides

Alternative Parents

Substituents

1,2,4-benzothiadiazine-1,1-dioxide
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Organosulfonic acid amide
Imidolactam
Benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Amidine
Azacycle
Dialkylthioether
Thioether
Sulfenyl compound
Organic oxide
Organosulfur compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:3047 )
benzothiadiazine (CHEBI:3047 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	231.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.013 g/L	Not Available
LogP	1.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	186.734	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000947

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.26	ALOGPS
logP	1.84	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	1.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.14 m³·mol⁻¹	ChemAxon
Polarizability	41.5 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]+	188.77	30932474
DeepCCS	[M-H]-	186.412	30932474
DeepCCS	[M-2H]-	219.857	30932474
DeepCCS	[M+Na]+	195.085	30932474
AllCCS	[M+H]+	189.7	32859911
AllCCS	[M+H-H2O]+	187.4	32859911
AllCCS	[M+NH4]+	191.9	32859911
AllCCS	[M+Na]+	192.5	32859911
AllCCS	[M-H]-	180.5	32859911
AllCCS	[M+Na-2H]-	180.4	32859911
AllCCS	[M+HCOO]-	180.5	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.	3.6 minutes	32390414
Predicted by Siyang on May 30, 2022	13.327 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.91 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2165.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	324.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	153.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	127.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	548.1 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	739.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	121.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1140.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	469.2 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	1369.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	400.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	314.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	195.6 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	83.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzthiazide	NS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C1	5555.8	Standard polar	33892256
Benzthiazide	NS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C1	3217.4	Standard non polar	33892256
Benzthiazide	NS(=O)(=O)C1=C(Cl)C=C2NC(CSCC3=CC=CC=C3)=NS(=O)(=O)C2=C1	4386.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzthiazide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	3753.7	Semi standard non polar	33892256
Benzthiazide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	3694.3	Standard non polar	33892256
Benzthiazide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	5348.8	Standard polar	33892256
Benzthiazide,1TMS,isomer #2	C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	3665.9	Semi standard non polar	33892256
Benzthiazide,1TMS,isomer #2	C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	3891.5	Standard non polar	33892256
Benzthiazide,1TMS,isomer #2	C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	5703.4	Standard polar	33892256
Benzthiazide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	3594.3	Semi standard non polar	33892256
Benzthiazide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	3900.3	Standard non polar	33892256
Benzthiazide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	5234.4	Standard polar	33892256
Benzthiazide,2TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O	3625.0	Semi standard non polar	33892256
Benzthiazide,2TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O	3870.5	Standard non polar	33892256
Benzthiazide,2TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O	4992.0	Standard polar	33892256
Benzthiazide,3TMS,isomer #1	C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C21	3584.3	Semi standard non polar	33892256
Benzthiazide,3TMS,isomer #1	C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C21	4222.7	Standard non polar	33892256
Benzthiazide,3TMS,isomer #1	C[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C21	5008.7	Standard polar	33892256
Benzthiazide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	3967.3	Semi standard non polar	33892256
Benzthiazide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	3970.4	Standard non polar	33892256
Benzthiazide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	5323.3	Standard polar	33892256
Benzthiazide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	3956.3	Semi standard non polar	33892256
Benzthiazide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	4157.2	Standard non polar	33892256
Benzthiazide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21	5684.8	Standard polar	33892256
Benzthiazide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	4107.0	Semi standard non polar	33892256
Benzthiazide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	4422.2	Standard non polar	33892256
Benzthiazide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(CSCC1=CC=CC=C1)=NS2(=O)=O	5195.8	Standard polar	33892256
Benzthiazide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O	4072.4	Semi standard non polar	33892256
Benzthiazide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O	4384.7	Standard non polar	33892256
Benzthiazide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(CSCC1=CC=CC=C1)=NS2(=O)=O	4936.3	Standard polar	33892256
Benzthiazide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C21	4247.2	Semi standard non polar	33892256
Benzthiazide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C21	5017.0	Standard non polar	33892256
Benzthiazide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(CSCC2=CC=CC=C2)=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C21	4951.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzthiazide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9242000000-15561d025e3aa0c75308	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzthiazide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-06r6-9624000000-532194fb14045a87f8de	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 10V, Positive-QTOF	splash10-001l-6202900000-2a70b9803c4b86c5dd1f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 20V, Positive-QTOF	splash10-00ko-9567100000-99dca328e8d7361a3afc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 40V, Positive-QTOF	splash10-01vo-9551000000-d1e207308294a5deee08	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 10V, Negative-QTOF	splash10-0iki-2069300000-96a7d5e7dc1269a42044	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 20V, Negative-QTOF	splash10-004r-9128100000-4954efc1704bdde45009	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 40V, Negative-QTOF	splash10-004i-9010000000-d24b3facbec316c46e12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 10V, Negative-QTOF	splash10-0a4i-0009000000-ef28da9b71b01c96fb7a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 20V, Negative-QTOF	splash10-0a4i-0009000000-8007d10d85565090d549	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 40V, Negative-QTOF	splash10-0fb9-9520000000-542b3b8a75568a776f6a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 10V, Positive-QTOF	splash10-001i-0001900000-e655f017360118b76da1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 20V, Positive-QTOF	splash10-001i-3101900000-f89180b83227d57566b2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzthiazide 40V, Positive-QTOF	splash10-0006-9000000000-688382bcfe309825184b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB00562	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00562	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00562

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2253

KEGG Compound ID

C07759

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzthiazide

METLIN ID

Not Available

PubChem Compound

2343

PDB ID

Not Available

ChEBI ID

3047

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Carbonic anhydrase 1

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:: CA1
Uniprot ID:: P00915
Molecular weight:: 28870.0

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

2. Carbonic anhydrase 2

General function:: Involved in carbonate dehydratase activity
Specific function:: Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
Gene Name:: CA2
Uniprot ID:: P00918
Molecular weight:: 29245.895

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
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. Carbonic anhydrase 12

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide.
Gene Name:: CA12
Uniprot ID:: O43570
Molecular weight:: 39450.615

References

Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [PubMed:19119014 ]

Enzyme Details

4. Solute carrier family 12 member 3

General function:: Involved in transport
Specific function:: Electrically silent transporter system. Mediates sodium and chloride reabsorption
Gene Name:: SLC12A3
Uniprot ID:: P55017
Molecular weight:: 113124.0

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

5. Carbonic anhydrase 4

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:: CA4
Uniprot ID:: P22748
Molecular weight:: 35032.075

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

6. Carbonic anhydrase 9

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
Gene Name:: CA9
Uniprot ID:: Q16790
Molecular weight:: 49697.36

References

Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [PubMed:19119014 ]

Showing metabocard for Benzthiazide (HMDB0014702)

MOL for HMDB0014702 (Benzthiazide)

3D MOL for HMDB0014702 (Benzthiazide)

3D SDF for HMDB0014702 (Benzthiazide)

3D-SDF for HMDB0014702 (Benzthiazide)

PDB for HMDB0014702 (Benzthiazide)

3D PDB for HMDB0014702 (Benzthiazide)

SMILES for HMDB0014702 (Benzthiazide)

INCHI for HMDB0014702 (Benzthiazide)

Structure for HMDB0014702 (Benzthiazide)

3D Structure for HMDB0014702 (Benzthiazide)

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

References

References

References