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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:39:52 UTC

Update Date

2021-09-26 22:59:52 UTC

HMDB ID

HMDB0249171

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bezitramide

Description

Bezitramide, also known as burgodin, 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. Based on a literature review a significant number of articles have been published on Bezitramide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bezitramide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bezitramide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

1459
  Mrv0541 02231215302D          

 37 41  0  0  0  0            999 V2000
    5.1661   -2.3526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649   -4.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6285    0.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -1.6886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -3.0165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800    2.9150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -0.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649   -0.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213    0.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8848    1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6921    1.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7173    4.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  2  0  0  0  0
  2 22  2  0  0  0  0
  3 10  1  0  0  0  0
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 31 36  2  0  0  0  0
 32 37  2  0  0  0  0
 33 36  1  0  0  0  0
 34 37  1  0  0  0  0
M  END

HMDB0249171
     RDKit          3D
Bezitramide
 69 73  0  0  0  0  0  0  0  0999 V2000
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 36 69  1  0
M  END

1459
  Mrv0541 02231215302D          

 37 41  0  0  0  0            999 V2000
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 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
 22 30  1  0  0  0  0
 24 25  2  0  0  0  0
 26 31  1  0  0  0  0
 27 32  1  0  0  0  0
 28 33  2  0  0  0  0
 29 34  2  0  0  0  0
 30 35  1  0  0  0  0
 31 36  2  0  0  0  0
 32 37  2  0  0  0  0
 33 36  1  0  0  0  0
 34 37  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249171

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)N1C(=O)N(C2CCN(CCC(C#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C31H32N4O2/c1-2-29(36)35-28-16-10-9-15-27(28)34(30(35)37)26-17-20-33(21-18-26)22-19-31(23-32,24-11-5-3-6-12-24)25-13-7-4-8-14-25/h3-16,26H,2,17-22H2,1H3

> <INCHI_KEY>
FLKWNFFCSSJANB-UHFFFAOYSA-N

> <FORMULA>
C31H32N4O2

> <MOLECULAR_WEIGHT>
492.6114

> <EXACT_MASS>
492.252526288

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.57782805239998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[4-(2-oxo-3-propanoyl-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
4.794030338333334

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.320154204728038

> <JCHEM_POLAR_SURFACE_AREA>
67.65

> <JCHEM_REFRACTIVITY>
155.25199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bezitramide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249171
     RDKit          3D
Bezitramide
 69 73  0  0  0  0  0  0  0  0999 V2000
    8.4791   -2.1492   -2.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7716   -1.1061   -1.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3140   -1.2357   -1.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8913   -2.1476   -2.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3496   -0.4726   -0.5888 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9891   -0.5980   -0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4664   -1.4525   -1.4468 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3843    0.2930    0.1038 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680    0.4601    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2615   -0.2590   -0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184    0.1615   -0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250    0.3466    0.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0166    0.5509    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634   -0.6551    0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3248   -0.2874    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4178    0.0984    1.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4908    0.3849    3.1075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7030    0.9064   -0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393    0.8888   -1.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    1.9912   -2.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4145    3.1504   -1.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4850    3.1886   -0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1355    2.0893    0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2171   -1.4396    0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0676   -2.3653   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9647   -3.4276   -0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0146   -3.5696    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1781   -2.6650    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2881   -1.6225    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0169   -0.5868    1.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.1006    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    1.0220    0.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1840    2.0441    1.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3110    2.6303    2.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5479    2.1833    1.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6540    1.1414    0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5351    0.5300    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1441   -3.1327   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5728   -2.0882   -1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3471   -1.9419   -3.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1486   -0.1028   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0880   -1.3464   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7491    1.5475    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581   -0.0382   -1.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774   -1.3657   -0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2153    1.1509   -1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7823   -0.6007   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1839    0.9214    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    1.3649   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6088   -1.4745    1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640   -1.0022   -0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3087   -0.0051   -2.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9140    1.9016   -3.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6836    4.0010   -2.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8093    4.0616    0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1918    2.1203    1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538   -2.2609   -1.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8360   -4.1595   -1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7228   -4.4022   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0226   -2.7882    1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4625   -0.9342    2.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5220   -0.5278    2.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0011   -1.6243    0.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9858   -0.9437    1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3361    0.7662    2.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1733    2.3723    1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1823    3.4284    2.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4562    2.6416    2.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6185    0.8187    0.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  3  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 15 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 12 30  1  0
 30 31  1  0
  8 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37  5  1  0
 31  9  1  0
 37 32  1  0
 23 18  1  0
 29 24  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  2 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 19 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 25 57  1  0
 26 58  1  0
 27 59  1  0
 28 60  1  0
 29 61  1  0
 30 62  1  0
 30 63  1  0
 31 64  1  0
 31 65  1  0
 33 66  1  0
 34 67  1  0
 35 68  1  0
 36 69  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1459                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.643  -4.392   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.654  -8.241   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       8.640   1.239   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.205  -3.152   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.205  -5.631   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.176   5.441   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.683  -1.688   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.190  -1.371   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.654  -0.542   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.668   0.093   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.133   0.922   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.118   2.703   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.625   3.021   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747  -3.622   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.104   4.484   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.103  -4.392   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747  -5.162   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.568   4.006   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.582   5.948   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -2.852   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -5.932   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.683  -7.094   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.640   4.963   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080  -3.622   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080  -5.162   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.714   5.035   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.554   7.094   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.885   2.499   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.089   6.266   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.190  -7.412   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.177   4.556   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.032   8.558   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.349   2.021   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.567   7.730   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.668  -8.876   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.495   3.049   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.539   8.876   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   22                                                            
CONECT    3   10   11   12                                                  
CONECT    4    7   14   16                                                  
CONECT    5   16   17   22                                                  
CONECT    6   23                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7   11                                                       
CONECT   10    3    8                                                       
CONECT   11    3    9                                                       
CONECT   12    3   13                                                       
CONECT   13   12   15                                                       
CONECT   14    4   17   20                                                  
CONECT   15   13   18   19   23                                             
CONECT   16    1    4    5                                                  
CONECT   17    5   14   21                                                  
CONECT   18   15   26   28                                                  
CONECT   19   15   27   29                                                  
CONECT   20   14   24                                                       
CONECT   21   17   25                                                       
CONECT   22    2    5   30                                                  
CONECT   23    6   15                                                       
CONECT   24   20   25                                                       
CONECT   25   21   24                                                       
CONECT   26   18   31                                                       
CONECT   27   19   32                                                       
CONECT   28   18   33                                                       
CONECT   29   19   34                                                       
CONECT   30   22   35                                                       
CONECT   31   26   36                                                       
CONECT   32   27   37                                                       
CONECT   33   28   36                                                       
CONECT   34   29   37                                                       
CONECT   35   30                                                            
CONECT   36   31   33                                                       
CONECT   37   32   34                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

COMPND    HMDB0249171
HETATM    1  C1  UNL     1       8.479  -2.149  -2.043  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.772  -1.106  -1.176  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.314  -1.236  -1.268  1.00  0.00           C  
HETATM    4  O1  UNL     1       5.891  -2.148  -2.057  1.00  0.00           O  
HETATM    5  N1  UNL     1       5.350  -0.473  -0.589  1.00  0.00           N  
HETATM    6  C4  UNL     1       3.989  -0.598  -0.691  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.466  -1.452  -1.447  1.00  0.00           O  
HETATM    8  N2  UNL     1       3.384   0.293   0.104  1.00  0.00           N  
HETATM    9  C5  UNL     1       1.968   0.460   0.262  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.262  -0.259  -0.864  1.00  0.00           C  
HETATM   11  C7  UNL     1      -0.218   0.161  -0.916  1.00  0.00           C  
HETATM   12  N3  UNL     1      -0.625   0.347   0.456  1.00  0.00           N  
HETATM   13  C8  UNL     1      -2.017   0.551   0.637  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.863  -0.655   0.331  1.00  0.00           C  
HETATM   15  C10 UNL     1      -4.325  -0.287   0.568  1.00  0.00           C  
HETATM   16  C11 UNL     1      -4.418   0.098   1.980  1.00  0.00           C  
HETATM   17  N4  UNL     1      -4.491   0.385   3.107  1.00  0.00           N  
HETATM   18  C12 UNL     1      -4.703   0.906  -0.238  1.00  0.00           C  
HETATM   19  C13 UNL     1      -4.639   0.889  -1.612  1.00  0.00           C  
HETATM   20  C14 UNL     1      -4.989   1.991  -2.360  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.415   3.150  -1.753  1.00  0.00           C  
HETATM   22  C16 UNL     1      -5.485   3.189  -0.382  1.00  0.00           C  
HETATM   23  C17 UNL     1      -5.136   2.089   0.341  1.00  0.00           C  
HETATM   24  C18 UNL     1      -5.217  -1.440   0.346  1.00  0.00           C  
HETATM   25  C19 UNL     1      -5.068  -2.365  -0.664  1.00  0.00           C  
HETATM   26  C20 UNL     1      -5.965  -3.428  -0.807  1.00  0.00           C  
HETATM   27  C21 UNL     1      -7.015  -3.570   0.060  1.00  0.00           C  
HETATM   28  C22 UNL     1      -7.178  -2.665   1.064  1.00  0.00           C  
HETATM   29  C23 UNL     1      -6.288  -1.623   1.194  1.00  0.00           C  
HETATM   30  C24 UNL     1      -0.017  -0.587   1.362  1.00  0.00           C  
HETATM   31  C25 UNL     1       1.429  -0.101   1.555  1.00  0.00           C  
HETATM   32  C26 UNL     1       4.324   1.022   0.745  1.00  0.00           C  
HETATM   33  C27 UNL     1       4.184   2.044   1.655  1.00  0.00           C  
HETATM   34  C28 UNL     1       5.311   2.630   2.170  1.00  0.00           C  
HETATM   35  C29 UNL     1       6.548   2.183   1.766  1.00  0.00           C  
HETATM   36  C30 UNL     1       6.654   1.141   0.838  1.00  0.00           C  
HETATM   37  C31 UNL     1       5.535   0.530   0.300  1.00  0.00           C  
HETATM   38  H1  UNL     1       8.144  -3.133  -1.708  1.00  0.00           H  
HETATM   39  H2  UNL     1       9.573  -2.088  -1.836  1.00  0.00           H  
HETATM   40  H3  UNL     1       8.347  -1.942  -3.115  1.00  0.00           H  
HETATM   41  H4  UNL     1       8.149  -0.103  -1.490  1.00  0.00           H  
HETATM   42  H5  UNL     1       8.088  -1.346  -0.145  1.00  0.00           H  
HETATM   43  H6  UNL     1       1.749   1.547   0.168  1.00  0.00           H  
HETATM   44  H7  UNL     1       1.658  -0.038  -1.853  1.00  0.00           H  
HETATM   45  H8  UNL     1       1.277  -1.366  -0.678  1.00  0.00           H  
HETATM   46  H9  UNL     1      -0.215   1.151  -1.428  1.00  0.00           H  
HETATM   47  H10 UNL     1      -0.782  -0.601  -1.455  1.00  0.00           H  
HETATM   48  H11 UNL     1      -2.184   0.921   1.673  1.00  0.00           H  
HETATM   49  H12 UNL     1      -2.345   1.365  -0.032  1.00  0.00           H  
HETATM   50  H13 UNL     1      -2.609  -1.474   1.032  1.00  0.00           H  
HETATM   51  H14 UNL     1      -2.664  -1.002  -0.682  1.00  0.00           H  
HETATM   52  H15 UNL     1      -4.309  -0.005  -2.113  1.00  0.00           H  
HETATM   53  H16 UNL     1      -4.914   1.902  -3.438  1.00  0.00           H  
HETATM   54  H17 UNL     1      -5.684   4.001  -2.333  1.00  0.00           H  
HETATM   55  H18 UNL     1      -5.809   4.062   0.170  1.00  0.00           H  
HETATM   56  H19 UNL     1      -5.192   2.120   1.441  1.00  0.00           H  
HETATM   57  H20 UNL     1      -4.254  -2.261  -1.338  1.00  0.00           H  
HETATM   58  H21 UNL     1      -5.836  -4.159  -1.616  1.00  0.00           H  
HETATM   59  H22 UNL     1      -7.723  -4.402  -0.046  1.00  0.00           H  
HETATM   60  H23 UNL     1      -8.023  -2.788   1.752  1.00  0.00           H  
HETATM   61  H24 UNL     1      -6.463  -0.934   2.005  1.00  0.00           H  
HETATM   62  H25 UNL     1      -0.522  -0.528   2.329  1.00  0.00           H  
HETATM   63  H26 UNL     1      -0.001  -1.624   0.986  1.00  0.00           H  
HETATM   64  H27 UNL     1       1.986  -0.944   1.959  1.00  0.00           H  
HETATM   65  H28 UNL     1       1.336   0.766   2.265  1.00  0.00           H  
HETATM   66  H29 UNL     1       3.173   2.372   1.952  1.00  0.00           H  
HETATM   67  H30 UNL     1       5.182   3.428   2.881  1.00  0.00           H  
HETATM   68  H31 UNL     1       7.456   2.642   2.168  1.00  0.00           H  
HETATM   69  H32 UNL     1       7.619   0.819   0.548  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3   41   42
CONECT    3    4    4    5
CONECT    5    6   37
CONECT    6    7    7    8
CONECT    8    9   32
CONECT    9   10   31   43
CONECT   10   11   44   45
CONECT   11   12   46   47
CONECT   12   13   30
CONECT   13   14   48   49
CONECT   14   15   50   51
CONECT   15   16   18   24
CONECT   16   17   17   17
CONECT   18   19   19   23
CONECT   19   20   52
CONECT   20   21   21   53
CONECT   21   22   54
CONECT   22   23   23   55
CONECT   23   56
CONECT   24   25   25   29
CONECT   25   26   57
CONECT   26   27   27   58
CONECT   27   28   59
CONECT   28   29   29   60
CONECT   29   61
CONECT   30   31   62   63
CONECT   31   64   65
CONECT   32   33   33   37
CONECT   33   34   66
CONECT   34   35   35   67
CONECT   35   36   68
CONECT   36   37   37   69
END

HMDB0249171
     RDKit          3D
Bezitramide
 69 73  0  0  0  0  0  0  0  0999 V2000
    8.4791   -2.1492   -2.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7716   -1.1061   -1.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3140   -1.2357   -1.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8913   -2.1476   -2.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3496   -0.4726   -0.5888 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9891   -0.5980   -0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4664   -1.4525   -1.4468 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3843    0.2930    0.1038 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680    0.4601    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2615   -0.2590   -0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184    0.1615   -0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250    0.3466    0.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0166    0.5509    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634   -0.6551    0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3248   -0.2874    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4178    0.0984    1.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4908    0.3849    3.1075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7030    0.9064   -0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393    0.8888   -1.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    1.9912   -2.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4145    3.1504   -1.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4850    3.1886   -0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1355    2.0893    0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2171   -1.4396    0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0676   -2.3653   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9647   -3.4276   -0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0146   -3.5696    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1781   -2.6650    1.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2881   -1.6225    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0169   -0.5868    1.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.1006    1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244    1.0220    0.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1840    2.0441    1.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3110    2.6303    2.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5479    2.1833    1.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6540    1.1414    0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5351    0.5300    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1441   -3.1327   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5728   -2.0882   -1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3471   -1.9419   -3.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1486   -0.1028   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0880   -1.3464   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7491    1.5475    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581   -0.0382   -1.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774   -1.3657   -0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2153    1.1509   -1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7823   -0.6007   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1839    0.9214    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447    1.3649   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6088   -1.4745    1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640   -1.0022   -0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3087   -0.0051   -2.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9140    1.9016   -3.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6836    4.0010   -2.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8093    4.0616    0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1918    2.1203    1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538   -2.2609   -1.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8360   -4.1595   -1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7228   -4.4022   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0226   -2.7882    1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4625   -0.9342    2.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5220   -0.5278    2.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0011   -1.6243    0.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9858   -0.9437    1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3361    0.7662    2.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1733    2.3723    1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1823    3.4284    2.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4562    2.6416    2.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6185    0.8187    0.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  3  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 15 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 12 30  1  0
 30 31  1  0
  8 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37  5  1  0
 31  9  1  0
 37 32  1  0
 23 18  1  0
 29 24  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  2 42  1  0
  9 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 19 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 25 57  1  0
 26 58  1  0
 27 59  1  0
 28 60  1  0
 29 61  1  0
 30 62  1  0
 30 63  1  0
 31 64  1  0
 31 65  1  0
 33 66  1  0
 34 67  1  0
 35 68  1  0
 36 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Burgodin	Kegg
Bezitramide monohydrochloride	MeSH

Chemical Formula

C₃₁H₃₂N₄O₂

Average Molecular Weight

492.6114

Monoisotopic Molecular Weight

492.252526288

IUPAC Name

4-[4-(2-oxo-3-propanoyl-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile

Traditional Name

bezitramide

CAS Registry Number

Not Available

SMILES

CCC(=O)N1C(=O)N(C2CCN(CCC(C#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C31H32N4O2/c1-2-29(36)35-28-16-10-9-15-27(28)34(30(35)37)26-17-20-33(21-18-26)22-19-31(23-32,24-11-5-3-6-12-24)25-13-7-4-8-14-25/h3-16,26H,2,17-22H2,1H3

InChI Key

FLKWNFFCSSJANB-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
Benzimidazole
N-acylimidazole
Imidazole-1-carbonyl group
N-acyl urea
Aralkylamine
Ureide
N-substituted imidazole
Piperidine
Azole
Imidazole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Urea
Azacycle
Nitrile
Carbonitrile
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0249171)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.35	ALOGPS
logP	4.79	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	8.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	67.65 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	155.25 m³·mol⁻¹	ChemAxon
Polarizability	55.58 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DeepCCS	[M-2H]-	244.348	30932474
DeepCCS	[M+Na]+	219.915	30932474
AllCCS	[M+H]+	221.3	32859911
AllCCS	[M+H-H2O]+	219.5	32859911
AllCCS	[M+NH4]+	222.9	32859911
AllCCS	[M+Na]+	223.4	32859911
AllCCS	[M-H]-	214.1	32859911
AllCCS	[M+Na-2H]-	214.8	32859911
AllCCS	[M+HCOO]-	215.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bezitramide	CCC(=O)N1C(=O)N(C2CCN(CCC(C#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C2=CC=CC=C12	4573.0	Standard polar	33892256
Bezitramide	CCC(=O)N1C(=O)N(C2CCN(CCC(C#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C2=CC=CC=C12	3741.5	Standard non polar	33892256
Bezitramide	CCC(=O)N1C(=O)N(C2CCN(CCC(C#N)(C3=CC=CC=C3)C3=CC=CC=C3)CC2)C2=CC=CC=C12	4218.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bezitramide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f7c-2954200000-da15db4440266867a920	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bezitramide 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 - Bezitramide 10V, Positive-QTOF	splash10-000i-0000900000-64f4ee6f9a3e6493fe31	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 20V, Positive-QTOF	splash10-00di-0130900000-469725c9a960948ea3a8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 40V, Positive-QTOF	splash10-00xr-2291300000-223bcf8afa1fb18d0984	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 10V, Negative-QTOF	splash10-0006-0000900000-393538337888b20bd777	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 20V, Negative-QTOF	splash10-000l-0330900000-7e8fc51bc5175e69594d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 40V, Negative-QTOF	splash10-001i-0970100000-cf9b6c30a2f6953f6a35	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 10V, Positive-QTOF	splash10-0006-0000900000-1f0e6cec0c2cd2b2793b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 20V, Positive-QTOF	splash10-03kl-0111900000-e1f67c5cf2956b6ad41f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 40V, Positive-QTOF	splash10-052f-1924700000-85da760214045ad30f90	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 10V, Negative-QTOF	splash10-0006-0000900000-647edfc7fb42d8cc0b83	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 20V, Negative-QTOF	splash10-01ox-0002900000-5a6589b058b46e83c373	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezitramide 40V, Negative-QTOF	splash10-0006-5495400000-ec80f53af139dc320b95	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01459

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

55675

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bezitramide

METLIN ID

Not Available

PubChem Compound

61791

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Bezitramide (HMDB0249171)

MOL for HMDB0249171 (Bezitramide)

3D MOL for HMDB0249171 (Bezitramide)

3D SDF for HMDB0249171 (Bezitramide)

3D-SDF for HMDB0249171 (Bezitramide)

PDB for HMDB0249171 (Bezitramide)

3D PDB for HMDB0249171 (Bezitramide)

SMILES for HMDB0249171 (Bezitramide)

INCHI for HMDB0249171 (Bezitramide)

Structure for HMDB0249171 (Bezitramide)

3D Structure for HMDB0249171 (Bezitramide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra