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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:03:08 UTC

Update Date

2021-09-26 23:07:42 UTC

HMDB ID

HMDB0254019

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lerisetron

Description

Lerisetron belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group. Lerisetron is a very strong basic compound (based on its pKa). Lerisetron (code name F-0930-RS) is a drug which acts as an antagonist at the 5-HT3 receptor. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lerisetron is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lerisetron 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

HMDB0254019
     RDKit          3D
Lerisetron
 42 45  0  0  0  0  0  0  0  0999 V2000
   -4.0241   -2.0536    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337   -2.4990    0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686   -1.9552    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493   -0.9615   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7224   -0.3986   -1.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438    0.7088   -0.8319 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101    0.6374   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7353   -0.4817    0.5049 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147   -1.1644   -0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1345   -2.4177    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7502   -2.0745    1.6898 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0148   -1.0511    2.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5738   -0.9815    1.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3160    1.9321    0.3015 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    2.7641   -0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    4.1497   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625    4.7674   -1.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423    3.9986   -1.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    2.6288   -1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4105    2.0028   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1400   -0.5159   -0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2180   -1.0487   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919   -2.4421    1.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -3.2734    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -2.3656    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055   -0.0732   -2.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -1.2361   -1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076   -1.4356   -1.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6143   -0.5101   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654   -3.0824    0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8765   -2.9419   -0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006   -1.6944    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764   -1.2825    3.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787   -0.0545    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826   -1.9913    1.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324   -0.2826    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245    4.7379    0.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787    5.8526   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150    4.4884   -2.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0786    2.0319   -2.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947    0.2486   -1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2062   -0.6801   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  7 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  4 21  1  0
 21 22  2  0
 22  1  1  0
 20  6  1  0
 13  8  1  0
 20 15  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
M  END

  Mrv1652310211603382D          

 22 25  0  0  0  0            999 V2000
    2.5399    2.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948    1.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428    1.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    2.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254019

> <DATABASE_NAME>
hmdb

> <SMILES>
C(N1C2=CC=CC=C2N=C1N1CCNCC1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H20N4/c1-2-6-15(7-3-1)14-22-17-9-5-4-8-16(17)20-18(22)21-12-10-19-11-13-21/h1-9,19H,10-14H2

> <INCHI_KEY>
PWWDCRQZITYKDV-UHFFFAOYSA-N

> <FORMULA>
C18H20N4

> <MOLECULAR_WEIGHT>
292.386

> <EXACT_MASS>
292.16879666

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.968256303762686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-benzyl-2-(piperazin-1-yl)-1H-1,3-benzodiazole

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.4640186873333336

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.836258554775767

> <JCHEM_POLAR_SURFACE_AREA>
33.09

> <JCHEM_REFRACTIVITY>
89.13509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lerisetron

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254019
     RDKit          3D
Lerisetron
 42 45  0  0  0  0  0  0  0  0999 V2000
   -4.0241   -2.0536    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337   -2.4990    0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686   -1.9552    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493   -0.9615   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7224   -0.3986   -1.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438    0.7088   -0.8319 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101    0.6374   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7353   -0.4817    0.5049 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147   -1.1644   -0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1345   -2.4177    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7502   -2.0745    1.6898 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0148   -1.0511    2.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5738   -0.9815    1.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3160    1.9321    0.3015 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    2.7641   -0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    4.1497   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625    4.7674   -1.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423    3.9986   -1.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    2.6288   -1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4105    2.0028   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1400   -0.5159   -0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2180   -1.0487   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919   -2.4421    1.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -3.2734    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -2.3656    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055   -0.0732   -2.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -1.2361   -1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076   -1.4356   -1.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6143   -0.5101   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654   -3.0824    0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8765   -2.9419   -0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006   -1.6944    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764   -1.2825    3.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787   -0.0545    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826   -1.9913    1.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324   -0.2826    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245    4.7379    0.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787    5.8526   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150    4.4884   -2.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0786    2.0319   -2.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947    0.2486   -1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2062   -0.6801   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  7 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  4 21  1  0
 21 22  2  0
 22  1  1  0
 20  6  1  0
 13  8  1  0
 20 15  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
M  END

HEADER    PROTEIN                                 21-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-OCT-16         0                                  
HETATM    1  C   UNK     0       4.741   4.841   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.217   3.376   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.187   2.232   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.680   2.552   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.204   4.017   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.235   5.161   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.320  -1.303   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -3.400  -1.303   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0254019
HETATM    1  C1  UNL     1      -4.024  -2.054   0.763  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.734  -2.499   0.977  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.669  -1.955   0.264  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.849  -0.962  -0.676  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.722  -0.399  -1.436  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.044   0.709  -0.832  1.00  0.00           N  
HETATM    7  C6  UNL     1       1.010   0.637  -0.008  1.00  0.00           C  
HETATM    8  N2  UNL     1       1.735  -0.482   0.505  1.00  0.00           N  
HETATM    9  C7  UNL     1       2.715  -1.164  -0.311  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.134  -2.418   0.429  1.00  0.00           C  
HETATM   11  N3  UNL     1       3.750  -2.075   1.690  1.00  0.00           N  
HETATM   12  C9  UNL     1       3.015  -1.051   2.404  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.574  -0.981   1.863  1.00  0.00           C  
HETATM   14  N4  UNL     1       1.316   1.932   0.302  1.00  0.00           N  
HETATM   15  C11 UNL     1       0.469   2.764  -0.318  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.323   4.150  -0.360  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.662   4.767  -1.104  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.542   3.999  -1.838  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.397   2.629  -1.796  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.410   2.003  -1.050  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.140  -0.516  -0.891  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.218  -1.049  -0.185  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.892  -2.442   1.290  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.598  -3.273   1.713  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.701  -2.366   0.486  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.105  -0.073  -2.451  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.019  -1.236  -1.698  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.308  -1.436  -1.301  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.614  -0.510  -0.500  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.265  -3.082   0.511  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.876  -2.942  -0.238  1.00  0.00           H  
HETATM   32  H10 UNL     1       4.701  -1.694   1.488  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.976  -1.282   3.469  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.479  -0.054   2.196  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.183  -1.991   1.826  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.032  -0.283   2.510  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.025   4.738   0.223  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.779   5.853  -1.137  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.315   4.488  -2.422  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.079   2.032  -2.375  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.395   0.249  -1.604  1.00  0.00           H  
HETATM   42  H20 UNL     1      -5.206  -0.680  -0.377  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3   24
CONECT    3    4    4   25
CONECT    4    5   21
CONECT    5    6   26   27
CONECT    6    7   20
CONECT    7    8   14   14
CONECT    8    9   13
CONECT    9   10   28   29
CONECT   10   11   30   31
CONECT   11   12   32
CONECT   12   13   33   34
CONECT   13   35   36
CONECT   14   15
CONECT   15   16   16   20
CONECT   16   17   37
CONECT   17   18   18   38
CONECT   18   19   39
CONECT   19   20   20   40
CONECT   21   22   22   41
CONECT   22   42
END

HMDB0254019
     RDKit          3D
Lerisetron
 42 45  0  0  0  0  0  0  0  0999 V2000
   -4.0241   -2.0536    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337   -2.4990    0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686   -1.9552    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493   -0.9615   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7224   -0.3986   -1.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438    0.7088   -0.8319 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101    0.6374   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7353   -0.4817    0.5049 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147   -1.1644   -0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1345   -2.4177    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7502   -2.0745    1.6898 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0148   -1.0511    2.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5738   -0.9815    1.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3160    1.9321    0.3015 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    2.7641   -0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3233    4.1497   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625    4.7674   -1.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423    3.9986   -1.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3973    2.6288   -1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4105    2.0028   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1400   -0.5159   -0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2180   -1.0487   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919   -2.4421    1.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -3.2734    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -2.3656    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055   -0.0732   -2.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -1.2361   -1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076   -1.4356   -1.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6143   -0.5101   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654   -3.0824    0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8765   -2.9419   -0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006   -1.6944    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764   -1.2825    3.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787   -0.0545    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826   -1.9913    1.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324   -0.2826    2.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245    4.7379    0.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787    5.8526   -1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150    4.4884   -2.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0786    2.0319   -2.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947    0.2486   -1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2062   -0.6801   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  7 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  4 21  1  0
 21 22  2  0
 22  1  1  0
 20  6  1  0
 13  8  1  0
 20 15  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Benzyl-2-(1-piperazinyl)benzimidazole	MeSH

Chemical Formula

C₁₈H₂₀N₄

Average Molecular Weight

292.386

Monoisotopic Molecular Weight

292.16879666

IUPAC Name

1-benzyl-2-(piperazin-1-yl)-1H-1,3-benzodiazole

Traditional Name

lerisetron

CAS Registry Number

Not Available

SMILES

C(N1C2=CC=CC=C2N=C1N1CCNCC1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H20N4/c1-2-6-15(7-3-1)14-22-17-9-5-4-8-16(17)20-18(22)21-12-10-19-11-13-21/h1-9,19H,10-14H2

InChI Key

PWWDCRQZITYKDV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

N-arylpiperazines

Alternative Parents

Substituents

N-arylpiperazine
Benzimidazole
Dialkylarylamine
Aminoimidazole
Monocyclic benzene moiety
N-substituted imidazole
Benzenoid
Imidazole
Azole
Heteroaromatic compound
Secondary amine
Secondary aliphatic amine
Azacycle
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
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: HMDB0254019)

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	3.01	ALOGPS
logP	3.46	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	8.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.14 m³·mol⁻¹	ChemAxon
Polarizability	32.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	163.904	30932474
DeepCCS	[M-H]-	161.546	30932474
DeepCCS	[M-2H]-	194.433	30932474
DeepCCS	[M+Na]+	169.997	30932474
AllCCS	[M+H]+	170.8	32859911
AllCCS	[M+H-H2O]+	167.4	32859911
AllCCS	[M+NH4]+	174.0	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	175.0	32859911
AllCCS	[M+Na-2H]-	174.3	32859911
AllCCS	[M+HCOO]-	173.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lerisetron	C(N1C2=CC=CC=C2N=C1N1CCNCC1)C1=CC=CC=C1	3549.2	Standard polar	33892256
Lerisetron	C(N1C2=CC=CC=C2N=C1N1CCNCC1)C1=CC=CC=C1	2659.4	Standard non polar	33892256
Lerisetron	C(N1C2=CC=CC=C2N=C1N1CCNCC1)C1=CC=CC=C1	2673.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lerisetron,1TMS,isomer #1	C[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3N2CC2=CC=CC=C2)CC1	2848.9	Semi standard non polar	33892256
Lerisetron,1TMS,isomer #1	C[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3N2CC2=CC=CC=C2)CC1	2811.8	Standard non polar	33892256
Lerisetron,1TMS,isomer #1	C[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3N2CC2=CC=CC=C2)CC1	3638.8	Standard polar	33892256
Lerisetron,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3N2CC2=CC=CC=C2)CC1	3004.5	Semi standard non polar	33892256
Lerisetron,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3N2CC2=CC=CC=C2)CC1	3003.9	Standard non polar	33892256
Lerisetron,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3N2CC2=CC=CC=C2)CC1	3782.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lerisetron GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9260000000-375995d5938b315fd4b0	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lerisetron 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 - Lerisetron 10V, Positive-QTOF	splash10-0006-1090000000-3e7216182c172437e1d6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 20V, Positive-QTOF	splash10-0006-4090000000-20bc87c25aa3d15c0fb2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 40V, Positive-QTOF	splash10-0006-9110000000-fa3031b86c2223d17c90	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 10V, Negative-QTOF	splash10-0006-0090000000-d760307f0eb127795941	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 20V, Negative-QTOF	splash10-0udi-1190000000-08b845ac619faa17eb13	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 40V, Negative-QTOF	splash10-0006-4910000000-e23278c5312dc66d7344	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 10V, Positive-QTOF	splash10-0006-0090000000-ee85e6ba33721a733e1f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 20V, Positive-QTOF	splash10-0006-1090000000-9c8591286e58a7c65d53	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 40V, Positive-QTOF	splash10-0006-8290000000-3d48921ec330333d4602	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 10V, Negative-QTOF	splash10-0006-0090000000-286ed2b65eb60f3df79d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 20V, Negative-QTOF	splash10-0006-0190000000-b7e75e0c9f3c8a54cf3c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lerisetron 40V, Negative-QTOF	splash10-06s9-1790000000-87e6dd94d798beedd131	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

DB12964

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lerisetron

METLIN ID

Not Available

PubChem Compound

65997

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 Lerisetron (HMDB0254019)

MOL for HMDB0254019 (Lerisetron)

3D MOL for HMDB0254019 (Lerisetron)

3D SDF for HMDB0254019 (Lerisetron)

3D-SDF for HMDB0254019 (Lerisetron)

PDB for HMDB0254019 (Lerisetron)

3D PDB for HMDB0254019 (Lerisetron)

SMILES for HMDB0254019 (Lerisetron)

INCHI for HMDB0254019 (Lerisetron)

Structure for HMDB0254019 (Lerisetron)

3D Structure for HMDB0254019 (Lerisetron)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra