NP-MRD: Showing NP-Card for Glibenclamide (NP0137402)

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Record Information

Version

2.0

Created at

2022-05-30 16:51:27 UTC

Updated at

2022-05-30 16:51:27 UTC

NP-MRD ID

NP0137402

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glibenclamide

Description

Glyburide, also known as glibenclamide or diabeta, 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. Glyburide is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, glyburide is involved in glibenclamide action pathway. Glibenclamide was first documented in 2005 (PMID: 16081479). An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group (PMID: 16634115).

Structure

MOL 3D MOL SDF PDB SMILES InChI

1016
  Mrv0541 02231215102D          

 33 35  0  0  0  0            999 V2000
    5.2224   -5.5689    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8563    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.9188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 31  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  9  1  0  0  0  0
  2 18  1  0  0  0  0
  3 17  2  0  0  0  0
  6 26  2  0  0  0  0
  7 28  1  0  0  0  0
  7 33  1  0  0  0  0
  8 11  1  0  0  0  0
  8 17  1  0  0  0  0
  9 17  1  0  0  0  0
 10 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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 16  1  0  0  0  0
 18 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  2  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 31  2  0  0  0  0
 30 32  2  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
    8.1485   -2.3228   -0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2848   -1.2286   -0.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5498    0.0556   -0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7636    0.3647   -1.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0164    1.6437   -1.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1086    2.6679   -1.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4558    4.3086   -2.3480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9170    2.3447   -1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6233    1.0425   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143    0.8497   -0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289    1.8780   -0.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8386   -0.3603    0.3505 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5035   -0.4275    0.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092   -0.0577   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312   -0.1674    0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    0.9096    1.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371    0.8113    2.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2718   -0.3804    2.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7282   -0.4156    3.1223 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.5224    0.4923    4.3156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0029   -1.7836    3.6859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0330    0.1497    2.1606 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3030   -0.4813    0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6707   -1.4277    0.4331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4376    0.0512    0.1743 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7434   -0.5712   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0832    0.4404   -2.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1965    1.3332   -1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4026    0.5496   -1.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1411   -0.6363   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9670   -1.4576   -0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7825   -1.4454    1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -1.3357    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6232   -2.3298   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5212   -3.2511   -0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8807   -2.3368    0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4613   -0.4645   -1.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9636    1.8739   -2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1871    3.1446   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3540   -1.2269    0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137   -1.4065    1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5486    0.3087    1.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4099   -0.8189   -0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4480    0.9549   -0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2159    1.8316    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189    1.6697    2.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6035    0.9446    2.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9848    0.8468    0.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9453   -1.2880   -1.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3599   -0.0726   -3.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1634    1.0598   -2.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8205    1.9650   -0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5196    2.0262   -2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0559    1.2587   -0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9832    0.2748   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0374   -1.2894   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9642   -0.3433    0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1652   -1.9919   -1.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7159   -2.1815   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3204   -2.3834    1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182   -2.1681    0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9  8  1  0
  8  6  2  0
  6  7  1  0
  6  5  1  0
  5  4  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 32  1  0
 32 33  2  0
 18 19  1  0
 19 20  2  0
 19 21  2  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
  4  3  1  0
 33 15  1  0
 31 26  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  8 39  1  0
  5 38  1  0
  4 37  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 16 45  1  0
 17 46  1  0
 32 60  1  0
 33 61  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
 27 50  1  0
 27 51  1  0
 28 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
 31 59  1  0
M  END

1016
  Mrv0541 02231215102D          

 33 35  0  0  0  0            999 V2000
    5.2224   -5.5689    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8563    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.9188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 31  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  9  1  0  0  0  0
  2 18  1  0  0  0  0
  3 17  2  0  0  0  0
  6 26  2  0  0  0  0
  7 28  1  0  0  0  0
  7 33  1  0  0  0  0
  8 11  1  0  0  0  0
  8 17  1  0  0  0  0
  9 17  1  0  0  0  0
 10 25  1  0  0  0  0
 10 26  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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 16  1  0  0  0  0
 18 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  2  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 31  2  0  0  0  0
 30 32  2  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137402

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)

> <INCHI_KEY>
ZNNLBTZKUZBEKO-UHFFFAOYSA-N

> <FORMULA>
C23H28ClN3O5S

> <MOLECULAR_WEIGHT>
494.004

> <EXACT_MASS>
493.143819418

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
51.75337429229601

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
3.7911100480000006

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.717745987330456

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.320179892066342

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1594498864691096

> <JCHEM_POLAR_SURFACE_AREA>
113.60000000000001

> <JCHEM_REFRACTIVITY>
126.9801

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glyburide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1016                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       9.748 -10.395   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       9.748   3.465   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      12.416   5.005   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.208   3.465   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.289   3.465   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.748  -5.005   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.414  -7.315   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      11.082   7.315   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.748   5.005   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       8.415  -5.005   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      12.416   8.085   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.750   7.315   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.416   9.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.083   8.085   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.750  10.395   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.083   9.625   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   5.775   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -1.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748  -2.695   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.082   1.155   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.082  -0.385   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.415  -3.465   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.081  -5.775   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.081  -7.315   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.748  -8.085   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.415  -8.085   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.748  -9.625   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.415  -9.625   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.081 -10.395   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.080  -8.085   0.000  0.00  0.00           C+0
CONECT    1   31                                                            
CONECT    2    4    5    9   18                                             
CONECT    3   17                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6   26                                                            
CONECT    7   28   33                                                       
CONECT    8   11   17                                                       
CONECT    9    2   17                                                       
CONECT   10   25   26                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   16                                                       
CONECT   16   14   15                                                       
CONECT   17    3    8    9                                                  
CONECT   18    2   21   22                                                  
CONECT   19   20   23   24                                                  
CONECT   20   19   25                                                       
CONECT   21   18   23                                                       
CONECT   22   18   24                                                       
CONECT   23   19   21                                                       
CONECT   24   19   22                                                       
CONECT   25   10   20                                                       
CONECT   26    6   10   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28    7   27   30                                                  
CONECT   29   27   31                                                       
CONECT   30   28   32                                                       
CONECT   31    1   29   32                                                  
CONECT   32   30   31                                                       
CONECT   33    7                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
1-((p-(2-(5-Chloro-O-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea	ChEBI
1-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea	ChEBI
5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide	ChEBI
Diabeta	ChEBI
Glibenclamida	ChEBI
Glibenclamide	ChEBI
Glibenclamidum	ChEBI
Glynase	ChEBI
Micronase	ChEBI
1-((p-(2-(5-Chloro-O-anisamido)ethyl)phenyl)sulphonyl)-3-cyclohexylurea	Generator
1-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulphonyl)-3-cyclohexylurea	Generator
5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulphonyl)phenyl)ethyl)-2-methoxybenzamide	Generator
Apo-glibenclamide	HMDB
Euglucon 5	HMDB
Euglucon N	HMDB
Glybenclamide	HMDB
Neogluconin	HMDB
Maninil	HMDB
Daonil	HMDB

Chemical Formula

C₂₃H₂₈ClN₃O₅S

Average Mass

494.0040 Da

Monoisotopic Mass

493.14382 Da

IUPAC Name

5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide

Traditional Name

glyburide

CAS Registry Number

Not Available

SMILES

COC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1

InChI Identifier

InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)

InChI Key

ZNNLBTZKUZBEKO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Anisole
Phenol ether
Methoxybenzene
Phenoxy compound
Chlorobenzene
Halobenzene
Sulfonylurea
Alkyl aryl ether
Aryl chloride
Aryl halide
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Carboximidic acid
Carboximidic acid derivative
Organic 1,3-dipolar compound
Ether
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:5441 )
N-sulfonylurea (CHEBI:5441 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.78	ALOGPS
logP	3.79	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.98 m³·mol⁻¹	ChemAxon
Polarizability	51.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0015151

DrugBank ID

DB01016

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3368

KEGG Compound ID

C07022

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glibenclamide

METLIN ID

Not Available

PubChem Compound

3488

PDB ID

Not Available

ChEBI ID

5441

Good Scents ID

Not Available

References

General References

Monami M, Luzzi C, Lamanna C, Chiasserini V, Addante F, Desideri CM, Masotti G, Marchionni N, Mannucci E: Three-year mortality in diabetic patients treated with different combinations of insulin secretagogues and metformin. Diabetes Metab Res Rev. 2006 Nov-Dec;22(6):477-82. doi: 10.1002/dmrr.642. [PubMed:16634115 ]
Robert R, Norez C, Becq F: Disruption of CFTR chloride channel alters mechanical properties and cAMP-dependent Cl- transport of mouse aortic smooth muscle cells. J Physiol. 2005 Oct 15;568(Pt 2):483-95. doi: 10.1113/jphysiol.2005.085019. Epub 2005 Aug 4. [PubMed:16081479 ]

Showing NP-Card for Glibenclamide (NP0137402)

MOL for NP0137402 (Glibenclamide)

3D MOL for NP0137402 (Glibenclamide)

3D SDF for NP0137402 (Glibenclamide)

3D-SDF for NP0137402 (Glibenclamide)

PDB for NP0137402 (Glibenclamide)

3D PDB for NP0137402 (Glibenclamide)

SMILES for NP0137402 (Glibenclamide)

INCHI for NP0137402 (Glibenclamide)

Structure for NP0137402 (Glibenclamide)

3D Structure for NP0137402 (Glibenclamide)