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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015213

Secondary Accession Numbers

HMDB15213

Metabolite Identification

Common Name

Diphenoxylate

Description

A meperidine congener used as an antidiarrheal, usually in combination with atropine. At high doses, it acts like morphine. Its unesterified metabolite difenoxin has similar properties and is used similarly. It has little or no analgesic activity. This medication is classified as a Schedule V under the Controlled Substances Act by the Food and Drug Administration (FDA) and the DEA in the United States when used in preparations. When diphenoxylate is used alone, it is classified as a Schedule II.

Structure

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

1081
  Mrv0541 02231215142D          

 34 37  0  0  0  0            999 V2000
    3.6020    2.8717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704    3.6842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396    0.5072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -1.5553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396    2.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5541    1.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5541    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4716    2.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3283    3.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2469    2.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -2.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9603    4.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8788    2.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7356    3.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    3.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -2.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -3.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -3.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -4.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 23  1  0  0  0  0
  2 12  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4 21  3  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 13  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 13 14  1  0  0  0  0
 14 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 21  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 24  2  0  0  0  0
 17 26  1  0  0  0  0
 18 25  2  0  0  0  0
 18 27  1  0  0  0  0
 19 22  2  0  0  0  0
 20 22  1  0  0  0  0
 23 28  1  0  0  0  0
 24 29  1  0  0  0  0
 25 30  1  0  0  0  0
 26 31  2  0  0  0  0
 27 32  2  0  0  0  0
 29 33  2  0  0  0  0
 30 34  2  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END

HMDB0015213
     RDKit          3D
Diphenoxylate
 66 69  0  0  0  0  0  0  0  0999 V2000
    6.9123    2.1425    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7409    1.7796    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7866    1.1095    0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6359    0.6809    1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559    0.8806    2.2512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6102   -0.0343    0.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2942   -1.2007   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304   -1.9398    0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8257   -3.0511    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051   -3.4595   -1.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8910   -2.7509   -2.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062   -1.6457   -1.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251    0.9684   -0.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    1.8587   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600    1.1178   -0.1222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    1.9290    0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.7624    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979    0.5056    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1163    0.2522    2.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9671    0.0478    3.1812 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9430   -0.6742   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701   -1.9096    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703   -3.0696   -0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3454   -2.9895   -1.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3033   -1.8039   -2.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -0.6610   -1.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8019    0.7534    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3184    1.1746   -0.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6910    1.4219   -0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5482    1.2463    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0254    0.8225    1.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6662    0.5824    1.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -0.1775    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4605   -0.3505    1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8121    3.1862   -0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9634    1.4890   -0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8920    1.9894    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3361    2.7363    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0962    1.1737    2.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2500   -1.6458    1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4610   -3.5897    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2212   -4.3240   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7887   -3.0709   -3.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -1.1138   -2.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5621    0.4853   -1.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9658    1.5542   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5035    1.9563    0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9999    2.8125   -0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002    3.0006    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106    2.0300    1.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1744    2.6084    0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7499    2.0492   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283   -1.9457    1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -4.0248    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -3.9030   -2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -1.8233   -3.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5834    0.2765   -2.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7023    1.3282   -1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0757    1.7547   -1.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6318    1.4411    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6753    0.6795    2.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2603    0.2419    2.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022   -0.4603    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -0.9439   -0.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5283   -1.4389    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169    0.1731    2.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  3  0
 18 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 18 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 15 33  1  0
 33 34  1  0
 34  6  1  0
 12  7  1  0
 26 21  1  0
 32 27  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 31 61  1  0
 32 62  1  0
 33 63  1  0
 33 64  1  0
 34 65  1  0
 34 66  1  0
M  END

1081
  Mrv0541 02231215142D          

 34 37  0  0  0  0            999 V2000
    3.6020    2.8717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704    3.6842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396    0.5072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -1.5553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396    2.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5541    1.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5541    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4716    2.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3283    3.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2469    2.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -2.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9603    4.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8788    2.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7356    3.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    3.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -2.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -3.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -3.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -4.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 23  1  0  0  0  0
  2 12  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4 21  3  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 13  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 13 14  1  0  0  0  0
 14 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 21  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 24  2  0  0  0  0
 17 26  1  0  0  0  0
 18 25  2  0  0  0  0
 18 27  1  0  0  0  0
 19 22  2  0  0  0  0
 20 22  1  0  0  0  0
 23 28  1  0  0  0  0
 24 29  1  0  0  0  0
 25 30  1  0  0  0  0
 26 31  2  0  0  0  0
 27 32  2  0  0  0  0
 29 33  2  0  0  0  0
 30 34  2  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015213

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3

> <INCHI_KEY>
HYPPXZBJBPSRLK-UHFFFAOYSA-N

> <FORMULA>
C30H32N2O2

> <MOLECULAR_WEIGHT>
452.5873

> <EXACT_MASS>
452.246378278

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
51.576568329906884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
5.884015037999999

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.49558763946689

> <JCHEM_POLAR_SURFACE_AREA>
53.33

> <JCHEM_REFRACTIVITY>
146.76189999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diphenoxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015213
     RDKit          3D
Diphenoxylate
 66 69  0  0  0  0  0  0  0  0999 V2000
    6.9123    2.1425    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7409    1.7796    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7866    1.1095    0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6359    0.6809    1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559    0.8806    2.2512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6102   -0.0343    0.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2942   -1.2007   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304   -1.9398    0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8257   -3.0511    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051   -3.4595   -1.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8910   -2.7509   -2.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062   -1.6457   -1.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251    0.9684   -0.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    1.8587   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600    1.1178   -0.1222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    1.9290    0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.7624    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979    0.5056    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1163    0.2522    2.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9671    0.0478    3.1812 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9430   -0.6742   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701   -1.9096    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703   -3.0696   -0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3454   -2.9895   -1.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3033   -1.8039   -2.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -0.6610   -1.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8019    0.7534    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3184    1.1746   -0.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6910    1.4219   -0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5482    1.2463    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0254    0.8225    1.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6662    0.5824    1.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -0.1775    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4605   -0.3505    1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8121    3.1862   -0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9634    1.4890   -0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8920    1.9894    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3361    2.7363    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0962    1.1737    2.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2500   -1.6458    1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4610   -3.5897    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2212   -4.3240   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7887   -3.0709   -3.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -1.1138   -2.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5621    0.4853   -1.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9658    1.5542   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5035    1.9563    0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9999    2.8125   -0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002    3.0006    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106    2.0300    1.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1744    2.6084    0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7499    2.0492   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283   -1.9457    1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -4.0248    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -3.9030   -2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -1.8233   -3.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5834    0.2765   -2.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7023    1.3282   -1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0757    1.7547   -1.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6318    1.4411    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6753    0.6795    2.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2603    0.2419    2.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022   -0.4603    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -0.9439   -0.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5283   -1.4389    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169    0.1731    2.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  3  0
 18 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 18 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 15 33  1  0
 33 34  1  0
 34  6  1  0
 12  7  1  0
 26 21  1  0
 32 27  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 31 61  1  0
 32 62  1  0
 33 63  1  0
 33 64  1  0
 34 65  1  0
 34 66  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1081                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.724   5.361   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.531   6.877   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       9.034   0.947   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      10.780  -2.903   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.034   4.027   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.700   3.257   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.368   3.257   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.700   1.717   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.368   1.717   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034  -0.593   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.214   5.017   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.264   5.361   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.700  -1.363   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.700  -2.903   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.946   6.534   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.661   4.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.160  -2.903   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.700  -4.443   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.126   7.523   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.840   5.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.240  -2.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.573   6.997   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.954   6.694   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.390  -4.237   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.034  -5.213   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.390  -1.570   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.366  -5.213   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414   6.694   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.850  -4.237   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.034  -6.753   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.850  -1.570   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.366  -6.753   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.080  -2.903   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.700  -7.523   0.000  0.00  0.00           C+0
CONECT    1   12   23                                                       
CONECT    2   12                                                            
CONECT    3    8    9   10                                                  
CONECT    4   21                                                            
CONECT    5    6    7   11   12                                             
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    3    6                                                       
CONECT    9    3    7                                                       
CONECT   10    3   13                                                       
CONECT   11    5   15   16                                                  
CONECT   12    1    2    5                                                  
CONECT   13   10   14                                                       
CONECT   14   13   17   18   21                                             
CONECT   15   11   19                                                       
CONECT   16   11   20                                                       
CONECT   17   14   24   26                                                  
CONECT   18   14   25   27                                                  
CONECT   19   15   22                                                       
CONECT   20   16   22                                                       
CONECT   21    4   14                                                       
CONECT   22   19   20                                                       
CONECT   23    1   28                                                       
CONECT   24   17   29                                                       
CONECT   25   18   30                                                       
CONECT   26   17   31                                                       
CONECT   27   18   32                                                       
CONECT   28   23                                                            
CONECT   29   24   33                                                       
CONECT   30   25   34                                                       
CONECT   31   26   33                                                       
CONECT   32   27   34                                                       
CONECT   33   29   31                                                       
CONECT   34   30   32                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0015213
HETATM    1  C1  UNL     1       6.912   2.142   0.345  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.741   1.780   1.231  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.787   1.110   0.423  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.636   0.681   1.038  1.00  0.00           C  
HETATM    5  O2  UNL     1       3.456   0.881   2.251  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.610  -0.034   0.197  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.294  -1.201  -0.366  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.130  -1.940   0.486  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.826  -3.051   0.059  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.705  -3.460  -1.241  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.891  -2.751  -2.093  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.206  -1.646  -1.648  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.125   0.968  -0.830  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.147   1.859  -0.062  1.00  0.00           C  
HETATM   15  N1  UNL     1      -0.160   1.118  -0.122  1.00  0.00           N  
HETATM   16  C13 UNL     1      -1.142   1.929   0.509  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.578   1.762   0.272  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.298   0.506   0.596  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.116   0.252   2.048  1.00  0.00           C  
HETATM   20  N2  UNL     1      -2.967   0.048   3.181  1.00  0.00           N  
HETATM   21  C17 UNL     1      -2.943  -0.674  -0.200  1.00  0.00           C  
HETATM   22  C18 UNL     1      -2.970  -1.910   0.451  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.670  -3.070  -0.224  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.345  -2.990  -1.544  1.00  0.00           C  
HETATM   25  C21 UNL     1      -2.303  -1.804  -2.229  1.00  0.00           C  
HETATM   26  C22 UNL     1      -2.610  -0.661  -1.519  1.00  0.00           C  
HETATM   27  C23 UNL     1      -4.802   0.753   0.467  1.00  0.00           C  
HETATM   28  C24 UNL     1      -5.318   1.175  -0.728  1.00  0.00           C  
HETATM   29  C25 UNL     1      -6.691   1.422  -0.873  1.00  0.00           C  
HETATM   30  C26 UNL     1      -7.548   1.246   0.185  1.00  0.00           C  
HETATM   31  C27 UNL     1      -7.025   0.822   1.384  1.00  0.00           C  
HETATM   32  C28 UNL     1      -5.666   0.582   1.510  1.00  0.00           C  
HETATM   33  C29 UNL     1       0.086  -0.178   0.485  1.00  0.00           C  
HETATM   34  C30 UNL     1       1.461  -0.351   1.077  1.00  0.00           C  
HETATM   35  H1  UNL     1       6.812   3.186  -0.018  1.00  0.00           H  
HETATM   36  H2  UNL     1       6.963   1.489  -0.565  1.00  0.00           H  
HETATM   37  H3  UNL     1       7.892   1.989   0.859  1.00  0.00           H  
HETATM   38  H4  UNL     1       5.336   2.736   1.653  1.00  0.00           H  
HETATM   39  H5  UNL     1       6.096   1.174   2.084  1.00  0.00           H  
HETATM   40  H6  UNL     1       4.250  -1.646   1.524  1.00  0.00           H  
HETATM   41  H7  UNL     1       5.461  -3.590   0.758  1.00  0.00           H  
HETATM   42  H8  UNL     1       5.221  -4.324  -1.648  1.00  0.00           H  
HETATM   43  H9  UNL     1       3.789  -3.071  -3.138  1.00  0.00           H  
HETATM   44  H10 UNL     1       2.579  -1.114  -2.342  1.00  0.00           H  
HETATM   45  H11 UNL     1       1.562   0.485  -1.631  1.00  0.00           H  
HETATM   46  H12 UNL     1       2.966   1.554  -1.243  1.00  0.00           H  
HETATM   47  H13 UNL     1       1.503   1.956   0.954  1.00  0.00           H  
HETATM   48  H14 UNL     1       1.000   2.812  -0.599  1.00  0.00           H  
HETATM   49  H15 UNL     1      -0.900   3.001   0.155  1.00  0.00           H  
HETATM   50  H16 UNL     1      -0.911   2.030   1.627  1.00  0.00           H  
HETATM   51  H17 UNL     1      -3.174   2.608   0.784  1.00  0.00           H  
HETATM   52  H18 UNL     1      -2.750   2.049  -0.821  1.00  0.00           H  
HETATM   53  H19 UNL     1      -3.228  -1.946   1.498  1.00  0.00           H  
HETATM   54  H20 UNL     1      -2.685  -4.025   0.261  1.00  0.00           H  
HETATM   55  H21 UNL     1      -2.110  -3.903  -2.073  1.00  0.00           H  
HETATM   56  H22 UNL     1      -2.043  -1.823  -3.257  1.00  0.00           H  
HETATM   57  H23 UNL     1      -2.583   0.277  -2.045  1.00  0.00           H  
HETATM   58  H24 UNL     1      -4.702   1.328  -1.596  1.00  0.00           H  
HETATM   59  H25 UNL     1      -7.076   1.755  -1.832  1.00  0.00           H  
HETATM   60  H26 UNL     1      -8.632   1.441   0.076  1.00  0.00           H  
HETATM   61  H27 UNL     1      -7.675   0.680   2.220  1.00  0.00           H  
HETATM   62  H28 UNL     1      -5.260   0.242   2.474  1.00  0.00           H  
HETATM   63  H29 UNL     1      -0.602  -0.460   1.279  1.00  0.00           H  
HETATM   64  H30 UNL     1      -0.003  -0.944  -0.326  1.00  0.00           H  
HETATM   65  H31 UNL     1       1.528  -1.439   1.349  1.00  0.00           H  
HETATM   66  H32 UNL     1       1.517   0.173   2.076  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   38   39
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   13   34
CONECT    7    8    8   12
CONECT    8    9   40
CONECT    9   10   10   41
CONECT   10   11   42
CONECT   11   12   12   43
CONECT   12   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   33
CONECT   16   17   49   50
CONECT   17   18   51   52
CONECT   18   19   21   27
CONECT   19   20   20   20
CONECT   21   22   22   26
CONECT   22   23   53
CONECT   23   24   24   54
CONECT   24   25   55
CONECT   25   26   26   56
CONECT   26   57
CONECT   27   28   28   32
CONECT   28   29   58
CONECT   29   30   30   59
CONECT   30   31   60
CONECT   31   32   32   61
CONECT   32   62
CONECT   33   34   63   64
CONECT   34   65   66
END

HMDB0015213
     RDKit          3D
Diphenoxylate
 66 69  0  0  0  0  0  0  0  0999 V2000
    6.9123    2.1425    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7409    1.7796    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7866    1.1095    0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6359    0.6809    1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559    0.8806    2.2512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6102   -0.0343    0.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2942   -1.2007   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304   -1.9398    0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8257   -3.0511    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051   -3.4595   -1.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8910   -2.7509   -2.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062   -1.6457   -1.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251    0.9684   -0.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    1.8587   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600    1.1178   -0.1222 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    1.9290    0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    1.7624    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979    0.5056    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1163    0.2522    2.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9671    0.0478    3.1812 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9430   -0.6742   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701   -1.9096    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703   -3.0696   -0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3454   -2.9895   -1.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3033   -1.8039   -2.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -0.6610   -1.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8019    0.7534    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3184    1.1746   -0.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6910    1.4219   -0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5482    1.2463    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0254    0.8225    1.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6662    0.5824    1.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -0.1775    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4605   -0.3505    1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8121    3.1862   -0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9634    1.4890   -0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8920    1.9894    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3361    2.7363    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0962    1.1737    2.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2500   -1.6458    1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4610   -3.5897    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2212   -4.3240   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7887   -3.0709   -3.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -1.1138   -2.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5621    0.4853   -1.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9658    1.5542   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5035    1.9563    0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9999    2.8125   -0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002    3.0006    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106    2.0300    1.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1744    2.6084    0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7499    2.0492   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283   -1.9457    1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847   -4.0248    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -3.9030   -2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -1.8233   -3.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5834    0.2765   -2.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7023    1.3282   -1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0757    1.7547   -1.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6318    1.4411    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6753    0.6795    2.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2603    0.2419    2.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022   -0.4603    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -0.9439   -0.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5283   -1.4389    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169    0.1731    2.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  3  0
 18 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 18 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 15 33  1  0
 33 34  1  0
 34  6  1  0
 12  7  1  0
 26 21  1  0
 32 27  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 31 61  1  0
 32 62  1  0
 33 63  1  0
 33 64  1  0
 34 65  1  0
 34 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(3-Cyano-3,3-diphenylpropyl)-4-phenyl-isonipecotic acid ethyl ester	ChEBI
2,2-Diphenyl-4-(4-carbethoxy-4-phenylpiperidino)butyronitrile	ChEBI
4-Ethoxycarbonyl-alpha,alpha,4-triphenyl-1-piperidinebutyronitrile	ChEBI
Difenoxilato	ChEBI
Diphenoxylatum	ChEBI
Ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylate	ChEBI
Ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylisonipecotate	ChEBI
1-(3-Cyano-3,3-diphenylpropyl)-4-phenyl-isonipecotate ethyl ester	Generator
4-Ethoxycarbonyl-a,a,4-triphenyl-1-piperidinebutyronitrile	Generator
4-Ethoxycarbonyl-α,α,4-triphenyl-1-piperidinebutyronitrile	Generator
Ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylic acid	Generator
Ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylisonipecotic acid	Generator
Diphenoxylic acid	Generator
Dea no. 9170	HMDB
Difenossilato	HMDB
Diphenoxalate	HMDB
Diphenoxylate monohydrochloride	HMDB
Monohydrochloride, diphenoxylate	HMDB
Hydrochloride, diphenoxylate	HMDB
Diphenoxylate hydrochloride	HMDB

Chemical Formula

C₃₀H₃₂N₂O₂

Average Molecular Weight

452.5873

Monoisotopic Molecular Weight

452.246378278

IUPAC Name

ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate

Traditional Name

diphenoxylate

CAS Registry Number

915-30-0

SMILES

CCOC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3

InChI Key

HYPPXZBJBPSRLK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylacetonitriles. These are cyclic aromatic compounds containing a diphenylacetonitrile moiety, which consists of a diphenylmethane linked to and acetonitrile to form 2,2-diphenylacetonitrile.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylacetonitriles

Direct Parent

Diphenylacetonitriles

Alternative Parents

Substituents

Diphenylacetonitrile
Diphenylmethane
Phenylpiperidine
Piperidinecarboxylic acid
Aralkylamine
Piperidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

ethyl ester (CHEBI:4639 )
tertiary amine (CHEBI:4639 )
nitrile (CHEBI:4639 )
piperidinecarboxylate ester (CHEBI:4639 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015213)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Diphenoxylate Action Pathway (PathBank: SMP0000675)

Role

Industrial application

Pharmaceutical industry

antidiarrhoeal drug (HMDB: HMDB0015213)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	221 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0015 g/L	Not Available
LogP	6.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	5.74	ALOGPS
logP	5.88	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.33 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	146.76 m³·mol⁻¹	ChemAxon
Polarizability	51.58 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	206.307	31661259
DarkChem	[M-H]-	198.709	31661259
DeepCCS	[M+H]+	207.887	30932474
DeepCCS	[M-H]-	205.491	30932474
DeepCCS	[M-2H]-	238.374	30932474
DeepCCS	[M+Na]+	213.921	30932474
AllCCS	[M+H]+	213.4	32859911
AllCCS	[M+H-H2O]+	211.3	32859911
AllCCS	[M+NH4]+	215.4	32859911
AllCCS	[M+Na]+	216.0	32859911
AllCCS	[M-H]-	210.1	32859911
AllCCS	[M+Na-2H]-	210.3	32859911
AllCCS	[M+HCOO]-	210.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diphenoxylate	CCOC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1	3819.2	Standard polar	33892256
Diphenoxylate	CCOC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1	3209.0	Standard non polar	33892256
Diphenoxylate	CCOC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1	3312.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Diphenoxylate EI-B (Non-derivatized)	splash10-0002-6591000000-e04da61bbde263b104e3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diphenoxylate EI-B (Non-derivatized)	splash10-0002-6591000000-e04da61bbde263b104e3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diphenoxylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-1129000000-033454565afde0495c58	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diphenoxylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diphenoxylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-2390000000-0d133bb29f340639db02	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate LC-ESI-QTOF , positive-QTOF	splash10-0udi-0000900000-e2841fe11576faaa404e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate LC-ESI-QTOF , positive-QTOF	splash10-0udi-0000900000-f16aa8a859221ed0173c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate LC-ESI-QTOF , positive-QTOF	splash10-0udi-0220900000-38d21080081c6d144498	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate LC-ESI-QTOF , positive-QTOF	splash10-0ap0-2920000000-ed4957b090e4b3a6f38d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate LC-ESI-QTOF , positive-QTOF	splash10-0aor-2900000000-becb90ead622a0131fdb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate , positive-QTOF	splash10-0udi-0210900000-f33819852c9168d0f8a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 40V, Positive-QTOF	splash10-0ap0-2930000000-27b1d68dee5988eaa135	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 30V, Positive-QTOF	splash10-0udi-0220900000-eb48236d047d8482c9db	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 10V, Positive-QTOF	splash10-0udi-0000900000-e2841fe11576faaa404e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 20V, Positive-QTOF	splash10-0udi-0000900000-f16aa8a859221ed0173c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 35V, Positive-QTOF	splash10-0ufr-1222900000-c125937f2ff362112070	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 50V, Positive-QTOF	splash10-0aor-2900000000-b973c5ffabd9b4d287ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 50V, Positive-QTOF	splash10-0aor-2900000000-5fa40194a7aea2fbeaff	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 30V, Positive-QTOF	splash10-0udi-0220900000-38d21080081c6d144498	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 40V, Positive-QTOF	splash10-0ap0-2920000000-ed4957b090e4b3a6f38d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 50V, Positive-QTOF	splash10-0aor-2900000000-becb90ead622a0131fdb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diphenoxylate 40V, Positive-QTOF	splash10-0ap0-2930000000-315293eb975bc2a18e68	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenoxylate 10V, Positive-QTOF	splash10-0udi-0011900000-4f997e63c9c65b9c3cf3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenoxylate 20V, Positive-QTOF	splash10-05g0-0344900000-56fc8f46c973ef960e51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenoxylate 40V, Positive-QTOF	splash10-00di-0971000000-b83c6e7e52cb3ee497b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenoxylate 10V, Negative-QTOF	splash10-0udi-0000900000-ec078fed32982bfba96e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenoxylate 20V, Negative-QTOF	splash10-0ufr-2343900000-eaa7ee09954f3184115d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenoxylate 40V, Negative-QTOF	splash10-116u-3941000000-217be57f7c4a4f20f18a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenoxylate 10V, Positive-QTOF	splash10-0udi-0003900000-ed80455eb1b0d171468d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diphenoxylate 20V, Positive-QTOF	splash10-0ugi-0009100000-945c8f0ee309cb0cc7df	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Diphenoxylate Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01081	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01081	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

DB01081

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

12919

KEGG Compound ID

C07872

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diphenoxylate

METLIN ID

Not Available

PubChem Compound

13505

PDB ID

Not Available

ChEBI ID

4639

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. Delta-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
Gene Name:: OPRD1
Uniprot ID:: P41143
Molecular weight:: 40412.3

References

Coupar IM: The peristaltic reflex in the rat ileum: evidence for functional mu- and delta-opiate receptors. J Pharm Pharmacol. 1995 Aug;47(8):643-6. [PubMed:8583364 ]

Enzyme Details

2. Mu-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:: OPRM1
Uniprot ID:: P35372
Molecular weight:: 44778.9

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Baker DE: Loperamide: a pharmacological review. Rev Gastroenterol Disord. 2007;7 Suppl 3:S11-8. [PubMed:18192961 ]
Corazziari E: Role of opioid ligands in the irritable bowel syndrome. Can J Gastroenterol. 1999 Mar;13 Suppl A:71A-75A. [PubMed:10202212 ]
Coupar IM: The peristaltic reflex in the rat ileum: evidence for functional mu- and delta-opiate receptors. J Pharm Pharmacol. 1995 Aug;47(8):643-6. [PubMed:8583364 ]
De Luca A, Coupar IM: Difenoxin and loperamide: studies on possible mechanisms of intestinal antisecretory action. Naunyn Schmiedebergs Arch Pharmacol. 1993 Feb;347(2):231-7. [PubMed:8386327 ]

Showing metabocard for Diphenoxylate (HMDB0015213)

MOL for HMDB0015213 (Diphenoxylate)

3D MOL for HMDB0015213 (Diphenoxylate)

3D SDF for HMDB0015213 (Diphenoxylate)

3D-SDF for HMDB0015213 (Diphenoxylate)

PDB for HMDB0015213 (Diphenoxylate)

3D PDB for HMDB0015213 (Diphenoxylate)

SMILES for HMDB0015213 (Diphenoxylate)

INCHI for HMDB0015213 (Diphenoxylate)

Structure for HMDB0015213 (Diphenoxylate)

3D Structure for HMDB0015213 (Diphenoxylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References