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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015406

Secondary Accession Numbers

HMDB15406

Metabolite Identification

Common Name

Glisoxepide

Description

Glisoxepide is one of the sulphonamide-derived oral antidiabetic drugs. It inhibits the uptake of bile acids into isolated rat hepatocytes. However it inhibits taurocholate uptake only in the absence of sodium ions. Glisoxepide uptake could be further inhibited by blockers of the hepatocellular monocarboxylate transporter, by the loop diuretic bumetanide, by 4,4'-diisothiocyano-2,2'-stilbenedisulfonate (DIDS) and by sulphate. These results are consistent with the transport of glisoxepide via the transport system for the unconjugated bile acid cholate. (PMID:1618280 , 9017793 ).

Structure

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

1289
  Mrv0541 02231215222D          

 31 33  0  0  0  0            999 V2000
    8.0632    0.4174    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0632    2.0674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6507    1.1318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4757   -0.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052   -3.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830   -4.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4922    2.8924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4922    2.0674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7777    0.8299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4907   -2.4702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6901   -4.5282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9047    4.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0797    4.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4191    4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5653    4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2355    3.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7488    3.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7777    1.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3487    0.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9198   -0.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052   -1.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6342    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3487   -0.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052   -2.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9198    0.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6342   -1.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4907   -3.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7763   -3.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0226   -3.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705   -3.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  9  1  0  0  0  0
  1 19  1  0  0  0  0
  2 18  2  0  0  0  0
  5 27  2  0  0  0  0
  6 11  1  0  0  0  0
  6 30  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 18  1  0  0  0  0
 10 24  1  0  0  0  0
 10 27  1  0  0  0  0
 11 28  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 19 22  2  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  2  0  0  0  0
 20 26  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 26  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0015406
     RDKit          3D
Glisoxepide
 58 60  0  0  0  0  0  0  0  0999 V2000
   12.0521   -0.9786    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6625   -0.4818    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5324   -0.6340   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4924   -0.0163    0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0906    0.0708   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251   -0.5430   -1.0742 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750    0.8287    0.7135 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8148    0.9470    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0537   -0.3864    0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6464   -0.0893   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -0.2093   -1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409    0.0950   -1.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463    0.5335   -1.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5434    0.9368   -1.6783 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4384    1.0370   -3.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962    2.3369   -1.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -0.1575   -1.2549 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9309    0.3570   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0251    1.6055   -0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9741   -0.5317   -0.2528 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1220   -0.1018    0.3635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8720    0.9100   -0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1175    0.6512   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1255   -0.2782   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3979   -0.8001    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6537   -1.2879    1.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487   -0.5605    1.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821    0.6531    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663    0.3435    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0303    0.4961    1.5518 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2899    0.2183    1.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4945   -0.2906   -0.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9120   -1.9660   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6514   -1.0561    1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4839   -1.1620   -1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5115    1.3236    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2496    1.5747    1.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6759    1.4422   -0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0852   -0.8746    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -1.0257   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696   -0.5496   -2.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    0.0027   -2.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7072   -1.1664   -1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722   -1.5478   -0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0788    1.8006    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2176    1.4154   -0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8164    0.1559   -1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5625    1.6420   -1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0501    0.3395   -0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5357   -1.0115   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6312   -1.2439    0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2209    0.2680    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0444   -1.0656    2.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4717   -2.3898    1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2271    0.2875    2.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4603   -1.2882    1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3815    0.9908    0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296    0.4311    1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 13 28  1  0
 28 29  2  0
  4 30  2  0
 30 31  1  0
 31  2  1  0
 29 10  1  0
 27 21  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 12 42  1  0
 17 43  1  0
 20 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 28 57  1  0
 29 58  1  0
M  END

1289
  Mrv0541 02231215222D          

 31 33  0  0  0  0            999 V2000
    8.0632    0.4174    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0632    2.0674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6507    1.1318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4757   -0.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052   -3.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830   -4.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4922    2.8924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4922    2.0674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7777    0.8299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4907   -2.4702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6901   -4.5282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9047    4.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0797    4.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4191    4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5653    4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2355    3.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7488    3.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7777    1.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3487    0.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9198   -0.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052   -1.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6342    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3487   -0.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052   -2.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9198    0.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6342   -1.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4907   -3.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7763   -3.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0226   -3.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705   -3.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  9  1  0  0  0  0
  1 19  1  0  0  0  0
  2 18  2  0  0  0  0
  5 27  2  0  0  0  0
  6 11  1  0  0  0  0
  6 30  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 18  1  0  0  0  0
 10 24  1  0  0  0  0
 10 27  1  0  0  0  0
 11 28  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 19 22  2  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  2  0  0  0  0
 20 26  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 26  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015406

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=NO1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H27N5O5S/c1-15-14-18(23-30-15)19(26)21-11-10-16-6-8-17(9-7-16)31(28,29)24-20(27)22-25-12-4-2-3-5-13-25/h6-9,14H,2-5,10-13H2,1H3,(H,21,26)(H2,22,24,27)

> <INCHI_KEY>
ZKUDBRCEOBOWLF-UHFFFAOYSA-N

> <FORMULA>
C20H27N5O5S

> <MOLECULAR_WEIGHT>
449.524

> <EXACT_MASS>
449.173289689

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
46.83471584924647

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{2-[4-({[(azepan-1-yl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-5-methyl-1,2-oxazole-3-carboxamide

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
1.4359763420000002

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.422062788921771

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.06666730351641

> <JCHEM_PKA_STRONGEST_BASIC>
1.593363977634887

> <JCHEM_POLAR_SURFACE_AREA>
133.64

> <JCHEM_REFRACTIVITY>
115.85730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glisoxepide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015406
     RDKit          3D
Glisoxepide
 58 60  0  0  0  0  0  0  0  0999 V2000
   12.0521   -0.9786    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6625   -0.4818    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5324   -0.6340   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4924   -0.0163    0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0906    0.0708   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251   -0.5430   -1.0742 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750    0.8287    0.7135 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8148    0.9470    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0537   -0.3864    0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6464   -0.0893   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -0.2093   -1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409    0.0950   -1.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463    0.5335   -1.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5434    0.9368   -1.6783 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4384    1.0370   -3.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962    2.3369   -1.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -0.1575   -1.2549 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9309    0.3570   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0251    1.6055   -0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9741   -0.5317   -0.2528 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1220   -0.1018    0.3635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8720    0.9100   -0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1175    0.6512   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1255   -0.2782   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3979   -0.8001    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6537   -1.2879    1.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487   -0.5605    1.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821    0.6531    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663    0.3435    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0303    0.4961    1.5518 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2899    0.2183    1.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4945   -0.2906   -0.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9120   -1.9660   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6514   -1.0561    1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4839   -1.1620   -1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5115    1.3236    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2496    1.5747    1.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6759    1.4422   -0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0852   -0.8746    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -1.0257   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696   -0.5496   -2.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    0.0027   -2.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7072   -1.1664   -1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722   -1.5478   -0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0788    1.8006    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2176    1.4154   -0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8164    0.1559   -1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5625    1.6420   -1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0501    0.3395   -0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5357   -1.0115   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6312   -1.2439    0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2209    0.2680    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0444   -1.0656    2.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4717   -2.3898    1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2271    0.2875    2.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4603   -1.2882    1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3815    0.9908    0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296    0.4311    1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 13 28  1  0
 28 29  2  0
  4 30  2  0
 30 31  1  0
 31  2  1  0
 29 10  1  0
 27 21  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 12 42  1  0
 17 43  1  0
 20 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 28 57  1  0
 29 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1289                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      15.051   0.779   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      15.051   3.859   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.281   2.113   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.821  -0.555   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.716  -6.921   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.382  -8.773   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      17.719   5.399   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      17.719   3.859   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      16.385   1.549   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       8.383  -4.611   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       6.888  -8.453   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      18.489   8.773   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.949   8.773   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.449   7.569   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.989   7.569   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.106   6.067   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.331   6.067   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.385   3.089   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.718   0.009   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.050  -1.531   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.716  -2.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.384   0.779   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.718  -1.531   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.716  -3.841   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.050   0.009   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.384  -2.301   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.383  -6.151   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.049  -6.921   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.642  -6.295   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.612  -7.439   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.080  -7.278   0.000  0.00  0.00           C+0
CONECT    1    3    4    9   19                                             
CONECT    2   18                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5   27                                                            
CONECT    6   11   30                                                       
CONECT    7    8   16   17                                                  
CONECT    8    7   18                                                       
CONECT    9    1   18                                                       
CONECT   10   24   27                                                       
CONECT   11    6   28                                                       
CONECT   12   13   14                                                       
CONECT   13   12   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16    7   14                                                       
CONECT   17    7   15                                                       
CONECT   18    2    8    9                                                  
CONECT   19    1   22   23                                                  
CONECT   20   21   25   26                                                  
CONECT   21   20   24                                                       
CONECT   22   19   25                                                       
CONECT   23   19   26                                                       
CONECT   24   10   21                                                       
CONECT   25   20   22                                                       
CONECT   26   20   23                                                       
CONECT   27    5   10   28                                                  
CONECT   28   11   27   29                                                  
CONECT   29   28   30                                                       
CONECT   30    6   29   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    HMDB0015406
HETATM    1  C1  UNL     1      12.052  -0.979   0.251  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.662  -0.482   0.532  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.532  -0.634  -0.223  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.492  -0.016   0.418  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.091   0.071  -0.023  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.725  -0.543  -1.074  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.175   0.829   0.713  1.00  0.00           N  
HETATM    8  C6  UNL     1       4.815   0.947   0.323  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.054  -0.386   0.305  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.646  -0.089  -0.151  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.311  -0.209  -1.485  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.041   0.095  -1.932  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.046   0.533  -1.081  1.00  0.00           C  
HETATM   14  S1  UNL     1      -1.543   0.937  -1.678  1.00  0.00           S  
HETATM   15  O2  UNL     1      -1.438   1.037  -3.187  1.00  0.00           O  
HETATM   16  O3  UNL     1      -1.896   2.337  -1.196  1.00  0.00           O  
HETATM   17  N2  UNL     1      -2.767  -0.157  -1.255  1.00  0.00           N  
HETATM   18  C12 UNL     1      -3.931   0.357  -0.610  1.00  0.00           C  
HETATM   19  O4  UNL     1      -4.025   1.605  -0.361  1.00  0.00           O  
HETATM   20  N3  UNL     1      -4.974  -0.532  -0.253  1.00  0.00           N  
HETATM   21  N4  UNL     1      -6.122  -0.102   0.363  1.00  0.00           N  
HETATM   22  C13 UNL     1      -6.872   0.910  -0.166  1.00  0.00           C  
HETATM   23  C14 UNL     1      -8.117   0.651  -1.040  1.00  0.00           C  
HETATM   24  C15 UNL     1      -9.126  -0.278  -0.265  1.00  0.00           C  
HETATM   25  C16 UNL     1      -8.398  -0.800   0.807  1.00  0.00           C  
HETATM   26  C17 UNL     1      -7.654  -1.288   1.894  1.00  0.00           C  
HETATM   27  C18 UNL     1      -6.249  -0.560   1.759  1.00  0.00           C  
HETATM   28  C19 UNL     1       0.382   0.653   0.255  1.00  0.00           C  
HETATM   29  C20 UNL     1       1.666   0.343   0.710  1.00  0.00           C  
HETATM   30  N5  UNL     1       9.030   0.496   1.552  1.00  0.00           N  
HETATM   31  O5  UNL     1      10.290   0.218   1.605  1.00  0.00           O  
HETATM   32  H1  UNL     1      12.495  -0.291  -0.504  1.00  0.00           H  
HETATM   33  H2  UNL     1      11.912  -1.966  -0.247  1.00  0.00           H  
HETATM   34  H3  UNL     1      12.651  -1.056   1.173  1.00  0.00           H  
HETATM   35  H4  UNL     1       9.484  -1.162  -1.173  1.00  0.00           H  
HETATM   36  H5  UNL     1       6.511   1.324   1.586  1.00  0.00           H  
HETATM   37  H6  UNL     1       4.250   1.575   1.065  1.00  0.00           H  
HETATM   38  H7  UNL     1       4.676   1.442  -0.661  1.00  0.00           H  
HETATM   39  H8  UNL     1       4.085  -0.875   1.282  1.00  0.00           H  
HETATM   40  H9  UNL     1       4.538  -1.026  -0.433  1.00  0.00           H  
HETATM   41  H10 UNL     1       3.070  -0.550  -2.181  1.00  0.00           H  
HETATM   42  H11 UNL     1       0.779   0.003  -2.991  1.00  0.00           H  
HETATM   43  H12 UNL     1      -2.707  -1.166  -1.440  1.00  0.00           H  
HETATM   44  H13 UNL     1      -4.872  -1.548  -0.462  1.00  0.00           H  
HETATM   45  H14 UNL     1      -7.079   1.801   0.507  1.00  0.00           H  
HETATM   46  H15 UNL     1      -6.218   1.415  -0.958  1.00  0.00           H  
HETATM   47  H16 UNL     1      -7.816   0.156  -1.961  1.00  0.00           H  
HETATM   48  H17 UNL     1      -8.562   1.642  -1.178  1.00  0.00           H  
HETATM   49  H18 UNL     1     -10.050   0.340  -0.030  1.00  0.00           H  
HETATM   50  H19 UNL     1      -9.536  -1.011  -1.008  1.00  0.00           H  
HETATM   51  H20 UNL     1      -7.631  -1.244   0.076  1.00  0.00           H  
HETATM   52  H21 UNL     1      -8.221   0.268   1.187  1.00  0.00           H  
HETATM   53  H22 UNL     1      -8.044  -1.066   2.933  1.00  0.00           H  
HETATM   54  H23 UNL     1      -7.472  -2.390   1.945  1.00  0.00           H  
HETATM   55  H24 UNL     1      -6.227   0.288   2.462  1.00  0.00           H  
HETATM   56  H25 UNL     1      -5.460  -1.288   1.920  1.00  0.00           H  
HETATM   57  H26 UNL     1      -0.381   0.991   0.937  1.00  0.00           H  
HETATM   58  H27 UNL     1       1.930   0.431   1.752  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    3   31
CONECT    3    4   35
CONECT    4    5   30   30
CONECT    5    6    6    7
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   11   11   29
CONECT   11   12   41
CONECT   12   13   13   42
CONECT   13   14   28
CONECT   14   15   15   16   16
CONECT   14   17
CONECT   17   18   43
CONECT   18   19   19   20
CONECT   20   21   44
CONECT   21   22   27
CONECT   22   23   45   46
CONECT   23   24   47   48
CONECT   24   25   49   50
CONECT   25   26   51   52
CONECT   26   27   53   54
CONECT   27   55   56
CONECT   28   29   29   57
CONECT   29   58
CONECT   30   31
END

HMDB0015406
     RDKit          3D
Glisoxepide
 58 60  0  0  0  0  0  0  0  0999 V2000
   12.0521   -0.9786    0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6625   -0.4818    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5324   -0.6340   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4924   -0.0163    0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0906    0.0708   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7251   -0.5430   -1.0742 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750    0.8287    0.7135 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8148    0.9470    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0537   -0.3864    0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6464   -0.0893   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -0.2093   -1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409    0.0950   -1.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0463    0.5335   -1.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5434    0.9368   -1.6783 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4384    1.0370   -3.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962    2.3369   -1.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -0.1575   -1.2549 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9309    0.3570   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0251    1.6055   -0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9741   -0.5317   -0.2528 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1220   -0.1018    0.3635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8720    0.9100   -0.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1175    0.6512   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1255   -0.2782   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3979   -0.8001    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6537   -1.2879    1.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487   -0.5605    1.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821    0.6531    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663    0.3435    0.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0303    0.4961    1.5518 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2899    0.2183    1.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4945   -0.2906   -0.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9120   -1.9660   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6514   -1.0561    1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4839   -1.1620   -1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5115    1.3236    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2496    1.5747    1.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6759    1.4422   -0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0852   -0.8746    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -1.0257   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696   -0.5496   -2.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    0.0027   -2.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7072   -1.1664   -1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722   -1.5478   -0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0788    1.8006    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2176    1.4154   -0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8164    0.1559   -1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5625    1.6420   -1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0501    0.3395   -0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5357   -1.0115   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6312   -1.2439    0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2209    0.2680    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0444   -1.0656    2.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4717   -2.3898    1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2271    0.2875    2.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4603   -1.2882    1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3815    0.9908    0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296    0.4311    1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 13 28  1  0
 28 29  2  0
  4 30  2  0
 30 31  1  0
 31  2  1  0
 29 10  1  0
 27 21  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 12 42  1  0
 17 43  1  0
 20 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 28 57  1  0
 29 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
RP-22410Glisoxepide	HMDB
4-(4-beta-(5-Methylisoxazol-3-carboxamidoethyl)phenylsulfonyl)-1,1-hexamethylenesemicarbazide	HMDB
Glisoxepid	HMDB
Pro-diaban	HMDB

Chemical Formula

C₂₀H₂₇N₅O₅S

Average Molecular Weight

449.524

Monoisotopic Molecular Weight

449.173289689

IUPAC Name

N-{2-[4-({[(azepan-1-yl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-5-methyl-1,2-oxazole-3-carboxamide

Traditional Name

glisoxepide

CAS Registry Number

25046-79-1

SMILES

CC1=CC(=NO1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC1

InChI Identifier

InChI=1S/C20H27N5O5S/c1-15-14-18(23-30-15)19(26)21-11-10-16-6-8-17(9-7-16)31(28,29)24-20(27)22-25-12-4-2-3-5-13-25/h6-9,14H,2-5,10-13H2,1H3,(H,21,26)(H2,22,24,27)

InChI Key

ZKUDBRCEOBOWLF-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
Benzenesulfonyl group
2-heteroaryl carboxamide
Azepane
Sulfonylurea
Azole
Isoxazole
Semicarbazide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Carbonic acid derivative
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Oxacycle
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015406)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	189 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.1 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	1.57	ALOGPS
logP	1.44	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	1.59	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	133.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.86 m³·mol⁻¹	ChemAxon
Polarizability	46.83 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	203.662	31661259
DarkChem	[M-H]-	201.793	31661259
DeepCCS	[M+H]+	206.167	30932474
DeepCCS	[M-H]-	203.809	30932474
DeepCCS	[M-2H]-	238.039	30932474
DeepCCS	[M+Na]+	213.115	30932474
AllCCS	[M+H]+	202.9	32859911
AllCCS	[M+H-H2O]+	200.8	32859911
AllCCS	[M+NH4]+	204.8	32859911
AllCCS	[M+Na]+	205.4	32859911
AllCCS	[M-H]-	195.6	32859911
AllCCS	[M+Na-2H]-	196.6	32859911
AllCCS	[M+HCOO]-	197.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glisoxepide	CC1=CC(=NO1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC1	5105.2	Standard polar	33892256
Glisoxepide	CC1=CC(=NO1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC1	2966.5	Standard non polar	33892256
Glisoxepide	CC1=CC(=NO1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CCCCCC1	3897.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glisoxepide,1TMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)NN3CCCCCC3)C=C2)[Si](C)(C)C)=NO1	4008.2	Semi standard non polar	33892256
Glisoxepide,1TMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)NN3CCCCCC3)C=C2)[Si](C)(C)C)=NO1	3368.3	Standard non polar	33892256
Glisoxepide,1TMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)NN3CCCCCC3)C=C2)[Si](C)(C)C)=NO1	6012.7	Standard polar	33892256
Glisoxepide,1TMS,isomer #2	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C)C=C2)=NO1	3872.2	Semi standard non polar	33892256
Glisoxepide,1TMS,isomer #2	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C)C=C2)=NO1	3399.7	Standard non polar	33892256
Glisoxepide,1TMS,isomer #2	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C)C=C2)=NO1	6074.2	Standard polar	33892256
Glisoxepide,1TMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C)C=C2)=NO1	3831.6	Semi standard non polar	33892256
Glisoxepide,1TMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C)C=C2)=NO1	3396.6	Standard non polar	33892256
Glisoxepide,1TMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C)C=C2)=NO1	6097.7	Standard polar	33892256
Glisoxepide,2TMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C)C=C2)[Si](C)(C)C)=NO1	3835.5	Semi standard non polar	33892256
Glisoxepide,2TMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C)C=C2)[Si](C)(C)C)=NO1	3548.8	Standard non polar	33892256
Glisoxepide,2TMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C)C=C2)[Si](C)(C)C)=NO1	5699.5	Standard polar	33892256
Glisoxepide,2TMS,isomer #2	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C)C=C2)[Si](C)(C)C)=NO1	3796.6	Semi standard non polar	33892256
Glisoxepide,2TMS,isomer #2	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C)C=C2)[Si](C)(C)C)=NO1	3543.0	Standard non polar	33892256
Glisoxepide,2TMS,isomer #2	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C)C=C2)[Si](C)(C)C)=NO1	5626.9	Standard polar	33892256
Glisoxepide,2TMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C)[Si](C)(C)C)C=C2)=NO1	3730.6	Semi standard non polar	33892256
Glisoxepide,2TMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C)[Si](C)(C)C)C=C2)=NO1	3591.4	Standard non polar	33892256
Glisoxepide,2TMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C)[Si](C)(C)C)C=C2)=NO1	5719.6	Standard polar	33892256
Glisoxepide,3TMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C)[Si](C)(C)C)C=C2)[Si](C)(C)C)=NO1	3714.0	Semi standard non polar	33892256
Glisoxepide,3TMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C)[Si](C)(C)C)C=C2)[Si](C)(C)C)=NO1	3760.3	Standard non polar	33892256
Glisoxepide,3TMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C)[Si](C)(C)C)C=C2)[Si](C)(C)C)=NO1	5227.3	Standard polar	33892256
Glisoxepide,1TBDMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)NN3CCCCCC3)C=C2)[Si](C)(C)C(C)(C)C)=NO1	4249.7	Semi standard non polar	33892256
Glisoxepide,1TBDMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)NN3CCCCCC3)C=C2)[Si](C)(C)C(C)(C)C)=NO1	3560.1	Standard non polar	33892256
Glisoxepide,1TBDMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)NN3CCCCCC3)C=C2)[Si](C)(C)C(C)(C)C)=NO1	5997.2	Standard polar	33892256
Glisoxepide,1TBDMS,isomer #2	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)=NO1	4117.3	Semi standard non polar	33892256
Glisoxepide,1TBDMS,isomer #2	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)=NO1	3598.8	Standard non polar	33892256
Glisoxepide,1TBDMS,isomer #2	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)=NO1	6083.3	Standard polar	33892256
Glisoxepide,1TBDMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)=NO1	4048.1	Semi standard non polar	33892256
Glisoxepide,1TBDMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)=NO1	3623.3	Standard non polar	33892256
Glisoxepide,1TBDMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)=NO1	6017.1	Standard polar	33892256
Glisoxepide,2TBDMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=NO1	4351.7	Semi standard non polar	33892256
Glisoxepide,2TBDMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=NO1	3934.4	Standard non polar	33892256
Glisoxepide,2TBDMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)NN3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=NO1	5636.2	Standard polar	33892256
Glisoxepide,2TBDMS,isomer #2	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=NO1	4273.3	Semi standard non polar	33892256
Glisoxepide,2TBDMS,isomer #2	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=NO1	3954.3	Standard non polar	33892256
Glisoxepide,2TBDMS,isomer #2	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)NC(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=NO1	5497.3	Standard polar	33892256
Glisoxepide,2TBDMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NO1	4237.4	Semi standard non polar	33892256
Glisoxepide,2TBDMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NO1	4023.7	Standard non polar	33892256
Glisoxepide,2TBDMS,isomer #3	CC1=CC(C(=O)NCCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=NO1	5623.5	Standard polar	33892256
Glisoxepide,3TBDMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=NO1	4442.8	Semi standard non polar	33892256
Glisoxepide,3TBDMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=NO1	4366.3	Standard non polar	33892256
Glisoxepide,3TBDMS,isomer #1	CC1=CC(C(=O)N(CCC2=CC=C(S(=O)(=O)N(C(=O)N(N3CCCCCC3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)=NO1	5164.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glisoxepide GC-MS (Non-derivatized) - 70eV, Positive	splash10-03du-9754100000-f939797a82a956924646	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glisoxepide 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 10V, Positive-QTOF	splash10-0w29-2826900000-f209a784879ee76f1525	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 20V, Positive-QTOF	splash10-03dj-2910000000-24728708fbbec7cb5802	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 40V, Positive-QTOF	splash10-0bt9-9800000000-9d7341f5d9538a72798a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 10V, Negative-QTOF	splash10-0002-2406900000-46c336c9d5635964011c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 20V, Negative-QTOF	splash10-01q9-9603100000-ba33ccd2212c2b505c5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 40V, Negative-QTOF	splash10-057i-9403100000-3aae831c5156639d8e24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 10V, Positive-QTOF	splash10-0f6x-5602900000-3af43796cb0817e2d912	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 20V, Positive-QTOF	splash10-0f75-4249500000-7dc0e0b2140e42b55c1a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 40V, Positive-QTOF	splash10-0f8a-3690200000-e9ac3ab3057e5f679402	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 10V, Negative-QTOF	splash10-0002-0004900000-de531b339eea989ce8ee	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 20V, Negative-QTOF	splash10-05o4-9028400000-6071396b430e7373feba	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glisoxepide 40V, Negative-QTOF	splash10-001i-9000000000-b71d839d4499f4904328	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB01289	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01289	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01289

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30380

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glisoxepide

METLIN ID

Not Available

PubChem Compound

32778

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

Fuckel D, Petzinger E: Interaction of sulfonylureas with the transport of bile acids into hepatocytes. Eur J Pharmacol. 1992 Mar 31;213(3):393-404. [PubMed:1618280 ]
Selvaag E: Photohemolytic potency of oral antidiabetic drugs in vitro: effects of antioxidants and a nitrogen atmosphere. Photodermatol Photoimmunol Photomed. 1996 Aug;12(4):166-70. [PubMed:9017793 ]

Enzymes

Enzyme Details

1. ATP-sensitive inward rectifier potassium channel 8

General function:: Involved in inward rectifier potassium channel activity
Specific function:: This potassium channel is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. Can be blocked by external barium
Gene Name:: KCNJ8
Uniprot ID:: Q15842
Molecular weight:: 47967.5

References

Szewczyk A, Wojcik G, Lobanov NA, Nalecz MJ: The mitochondrial sulfonylurea receptor: identification and characterization. Biochem Biophys Res Commun. 1997 Jan 23;230(3):611-5. [PubMed:9015372 ]
Sato T, Costa AD, Saito T, Ogura T, Ishida H, Garlid KD, Nakaya H: Bepridil, an antiarrhythmic drug, opens mitochondrial KATP channels, blocks sarcolemmal KATP channels, and confers cardioprotection. J Pharmacol Exp Ther. 2006 Jan;316(1):182-8. Epub 2005 Sep 20. [PubMed:16174795 ]

Enzyme Details

2. ATP-binding cassette sub-family C member 8

General function:: Involved in ATP binding
Specific function:: Putative subunit of the beta-cell ATP-sensitive potassium channel (KATP). Regulator of ATP-sensitive K(+) channels and insulin release
Gene Name:: ABCC8
Uniprot ID:: Q09428
Molecular weight:: 177006.4

References

Gribble FM, Ashcroft FM: Sulfonylurea sensitivity of adenosine triphosphate-sensitive potassium channels from beta cells and extrapancreatic tissues. Metabolism. 2000 Oct;49(10 Suppl 2):3-6. [PubMed:11078468 ]
Harrower A: Gliclazide modified release: from once-daily administration to 24-hour blood glucose control. Metabolism. 2000 Oct;49(10 Suppl 2):7-11. [PubMed:11078469 ]
Lawrence CL, Proks P, Rodrigo GC, Jones P, Hayabuchi Y, Standen NB, Ashcroft FM: Gliclazide produces high-affinity block of KATP channels in mouse isolated pancreatic beta cells but not rat heart or arterial smooth muscle cells. Diabetologia. 2001 Aug;44(8):1019-25. [PubMed:11484080 ]
Reimann F, Ashcroft FM, Gribble FM: Structural basis for the interference between nicorandil and sulfonylurea action. Diabetes. 2001 Oct;50(10):2253-9. [PubMed:11574406 ]
Proks P, Reimann F, Green N, Gribble F, Ashcroft F: Sulfonylurea stimulation of insulin secretion. Diabetes. 2002 Dec;51 Suppl 3:S368-76. [PubMed:12475777 ]

Showing metabocard for Glisoxepide (HMDB0015406)

MOL for HMDB0015406 (Glisoxepide)

3D MOL for HMDB0015406 (Glisoxepide)

3D SDF for HMDB0015406 (Glisoxepide)

3D-SDF for HMDB0015406 (Glisoxepide)

PDB for HMDB0015406 (Glisoxepide)

3D PDB for HMDB0015406 (Glisoxepide)

SMILES for HMDB0015406 (Glisoxepide)

INCHI for HMDB0015406 (Glisoxepide)

Structure for HMDB0015406 (Glisoxepide)

3D Structure for HMDB0015406 (Glisoxepide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References