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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 19:42:32 UTC

Update Date

2021-09-26 23:15:06 UTC

HMDB ID

HMDB0258307

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Sipatrigine

Description

Sipatrigine, also known as BW619C89, 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. Based on a literature review a significant number of articles have been published on Sipatrigine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Sipatrigine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Sipatrigine 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

HMDB0258307
     RDKit          3D
Sipatrigine
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.8702    0.1021   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579    0.2950    0.3168 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8444    1.3995   -0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5849    1.0713   -0.9381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -0.1680   -0.5139 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -0.2471   -0.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637   -1.3950   -0.1574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025   -1.5023    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -0.3458   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5753   -0.3610    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3958    0.3462   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7523    0.3256   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8064    1.2237   -1.5412 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.2911   -0.3979    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4381   -1.0957    1.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1536   -1.9870    2.7676 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0667   -1.0886    1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0039   -1.9846    2.3428 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5053    0.8584   -0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1965    2.1058   -0.2686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    0.8894   -0.3916 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -1.3457   -0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8692   -0.8586    0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1812   -0.9457   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6391    0.6247    0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9288    0.6063   -1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151    2.0844    0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    1.9849   -0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573    1.0110   -2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779    1.9084   -0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8231   -2.4856    0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772    0.9176   -1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3663   -0.3928    0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525    2.5856   -1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6396    2.5627    0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2443   -1.8152   -1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967   -2.0845    0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779   -1.6980    0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265   -0.7039    1.7533 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 19 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  8 31  1  0
 11 32  1  0
 14 33  1  0
 20 34  1  0
 20 35  1  0
 22 36  1  0
 22 37  1  0
 23 38  1  0
 23 39  1  0
M  END


  Mrv1652309112121422D          

 23 25  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 17 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258307

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC1)C1=NC=C(C(N)=N1)C1=CC(Cl)=CC(Cl)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C15H16Cl3N5/c1-22-2-4-23(5-3-22)15-20-8-11(14(19)21-15)10-6-9(16)7-12(17)13(10)18/h6-8H,2-5H2,1H3,(H2,19,20,21)

> <INCHI_KEY>
PDOCBJADCWMDGL-UHFFFAOYSA-N

> <FORMULA>
C15H16Cl3N5

> <MOLECULAR_WEIGHT>
372.68

> <EXACT_MASS>
371.0471286

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
37.15507621745996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-methylpiperazin-1-yl)-5-(2,3,5-trichlorophenyl)pyrimidin-4-amine

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
3.9085758826666663

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.24363210507999

> <JCHEM_POLAR_SURFACE_AREA>
58.28

> <JCHEM_REFRACTIVITY>
97.71149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-methylpiperazin-1-yl)-5-(2,3,5-trichlorophenyl)pyrimidin-4-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258307
     RDKit          3D
Sipatrigine
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.8702    0.1021   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579    0.2950    0.3168 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8444    1.3995   -0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5849    1.0713   -0.9381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -0.1680   -0.5139 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -0.2471   -0.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637   -1.3950   -0.1574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025   -1.5023    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -0.3458   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5753   -0.3610    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3958    0.3462   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7523    0.3256   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8064    1.2237   -1.5412 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.2911   -0.3979    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4381   -1.0957    1.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1536   -1.9870    2.7676 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0667   -1.0886    1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0039   -1.9846    2.3428 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5053    0.8584   -0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1965    2.1058   -0.2686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    0.8894   -0.3916 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -1.3457   -0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8692   -0.8586    0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1812   -0.9457   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6391    0.6247    0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9288    0.6063   -1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151    2.0844    0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    1.9849   -0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573    1.0110   -2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779    1.9084   -0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8231   -2.4856    0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772    0.9176   -1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3663   -0.3928    0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525    2.5856   -1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6396    2.5627    0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2443   -1.8152   -1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967   -2.0845    0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779   -1.6980    0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265   -0.7039    1.7533 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 19 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  8 31  1  0
 11 32  1  0
 14 33  1  0
 20 34  1  0
 20 35  1  0
 22 36  1  0
 22 37  1  0
 23 38  1  0
 23 39  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -6.930   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.334 -10.010   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.667 -12.320   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.000 -12.320   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      -1.334 -14.630   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.000 -18.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0      -1.334 -16.170   0.000  0.00  0.00          Cl+0
HETATM   22 Cl   UNK     0      -1.334 -19.250   0.000  0.00  0.00          Cl+0
HETATM   23 Cl   UNK     0       4.001 -19.250   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12                                                            
CONECT   15   11   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0258307
HETATM    1  C1  UNL     1       5.870   0.102  -0.223  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.558   0.295   0.317  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.844   1.400  -0.177  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.585   1.071  -0.938  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.993  -0.168  -0.514  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.587  -0.247  -0.361  1.00  0.00           C  
HETATM    7  N3  UNL     1      -0.064  -1.395  -0.157  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.403  -1.502   0.019  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.142  -0.346  -0.015  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.575  -0.361   0.183  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.396   0.346  -0.672  1.00  0.00           C  
HETATM   12  C9  UNL     1      -5.752   0.326  -0.459  1.00  0.00           C  
HETATM   13 CL1  UNL     1      -6.806   1.224  -1.541  1.00  0.00          CL  
HETATM   14  C10 UNL     1      -6.291  -0.398   0.605  1.00  0.00           C  
HETATM   15  C11 UNL     1      -5.438  -1.096   1.444  1.00  0.00           C  
HETATM   16 CL2  UNL     1      -6.154  -1.987   2.768  1.00  0.00          CL  
HETATM   17  C12 UNL     1      -4.067  -1.089   1.246  1.00  0.00           C  
HETATM   18 CL3  UNL     1      -3.004  -1.985   2.343  1.00  0.00          CL  
HETATM   19  C13 UNL     1      -1.505   0.858  -0.224  1.00  0.00           C  
HETATM   20  N4  UNL     1      -2.196   2.106  -0.269  1.00  0.00           N  
HETATM   21  N5  UNL     1      -0.174   0.889  -0.392  1.00  0.00           N  
HETATM   22  C14 UNL     1       2.781  -1.346  -0.204  1.00  0.00           C  
HETATM   23  C15 UNL     1       3.869  -0.859   0.734  1.00  0.00           C  
HETATM   24  H1  UNL     1       6.181  -0.946  -0.307  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.639   0.625   0.396  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.929   0.606  -1.226  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.615   2.084   0.677  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.494   1.985  -0.861  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.757   1.011  -2.036  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.878   1.908  -0.787  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.823  -2.486   0.169  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.977   0.918  -1.518  1.00  0.00           H  
HETATM   33  H10 UNL     1      -7.366  -0.393   0.752  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.253   2.586  -1.205  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.640   2.563   0.546  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.244  -1.815  -1.068  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.197  -2.084   0.380  1.00  0.00           H  
HETATM   38  H15 UNL     1       4.578  -1.698   0.867  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.426  -0.704   1.753  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   23
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   22
CONECT    6    7    7   21
CONECT    7    8
CONECT    8    9    9   31
CONECT    9   10   19
CONECT   10   11   11   17
CONECT   11   12   32
CONECT   12   13   14   14
CONECT   14   15   33
CONECT   15   16   17   17
CONECT   17   18
CONECT   19   20   21   21
CONECT   20   34   35
CONECT   22   23   36   37
CONECT   23   38   39
END

HMDB0258307
     RDKit          3D
Sipatrigine
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.8702    0.1021   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579    0.2950    0.3168 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8444    1.3995   -0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5849    1.0713   -0.9381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -0.1680   -0.5139 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -0.2471   -0.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637   -1.3950   -0.1574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025   -1.5023    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -0.3458   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5753   -0.3610    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3958    0.3462   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7523    0.3256   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8064    1.2237   -1.5412 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.2911   -0.3979    0.6050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4381   -1.0957    1.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1536   -1.9870    2.7676 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0667   -1.0886    1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0039   -1.9846    2.3428 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5053    0.8584   -0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1965    2.1058   -0.2686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    0.8894   -0.3916 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -1.3457   -0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8692   -0.8586    0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1812   -0.9457   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6391    0.6247    0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9288    0.6063   -1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151    2.0844    0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    1.9849   -0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7573    1.0110   -2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779    1.9084   -0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8231   -2.4856    0.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772    0.9176   -1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3663   -0.3928    0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525    2.5856   -1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6396    2.5627    0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2443   -1.8152   -1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967   -2.0845    0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779   -1.6980    0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265   -0.7039    1.7533 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 19 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  8 31  1  0
 11 32  1  0
 14 33  1  0
 20 34  1  0
 20 35  1  0
 22 36  1  0
 22 37  1  0
 23 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
BW619c89	Kegg
4-Amino-2-(4-methyl-1-piperazinyl)-5-(2,3,5-trichlorophenyl)pyrimidine	HMDB

Chemical Formula

C₁₅H₁₆Cl₃N₅

Average Molecular Weight

372.68

Monoisotopic Molecular Weight

371.0471286

IUPAC Name

2-(4-methylpiperazin-1-yl)-5-(2,3,5-trichlorophenyl)pyrimidin-4-amine

Traditional Name

2-(4-methylpiperazin-1-yl)-5-(2,3,5-trichlorophenyl)pyrimidin-4-amine

CAS Registry Number

Not Available

SMILES

CN1CCN(CC1)C1=NC=C(C(N)=N1)C1=CC(Cl)=CC(Cl)=C1Cl

InChI Identifier

InChI=1S/C15H16Cl3N5/c1-22-2-4-23(5-3-22)15-20-8-11(14(19)21-15)10-6-9(16)7-12(17)13(10)18/h6-8H,2-5H2,1H3,(H2,19,20,21)

InChI Key

PDOCBJADCWMDGL-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
Dialkylarylamine
Aminopyrimidine
Chlorobenzene
Halobenzene
N-methylpiperazine
N-alkylpiperazine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Pyrimidine
Imidolactam
Benzenoid
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Azacycle
Amine
Primary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidines (CHEBI:34977 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	3.62	ALOGPS
logP	3.91	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	7.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.28 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.71 m³·mol⁻¹	ChemAxon
Polarizability	37.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	173.899	30932474
DeepCCS	[M-H]-	171.541	30932474
DeepCCS	[M-2H]-	205.197	30932474
DeepCCS	[M+Na]+	180.424	30932474
AllCCS	[M+H]+	180.0	32859911
AllCCS	[M+H-H2O]+	177.1	32859911
AllCCS	[M+NH4]+	182.6	32859911
AllCCS	[M+Na]+	183.4	32859911
AllCCS	[M-H]-	179.7	32859911
AllCCS	[M+Na-2H]-	179.5	32859911
AllCCS	[M+HCOO]-	179.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sipatrigine	CN1CCN(CC1)C1=NC=C(C(N)=N1)C1=CC(Cl)=CC(Cl)=C1Cl	3851.7	Standard polar	33892256
Sipatrigine	CN1CCN(CC1)C1=NC=C(C(N)=N1)C1=CC(Cl)=CC(Cl)=C1Cl	2864.1	Standard non polar	33892256
Sipatrigine	CN1CCN(CC1)C1=NC=C(C(N)=N1)C1=CC(Cl)=CC(Cl)=C1Cl	2949.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sipatrigine,1TMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N[Si](C)(C)C)=N2)CC1	3036.8	Semi standard non polar	33892256
Sipatrigine,1TMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N[Si](C)(C)C)=N2)CC1	3151.0	Standard non polar	33892256
Sipatrigine,1TMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N[Si](C)(C)C)=N2)CC1	4064.2	Standard polar	33892256
Sipatrigine,2TMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N([Si](C)(C)C)[Si](C)(C)C)=N2)CC1	2941.4	Semi standard non polar	33892256
Sipatrigine,2TMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N([Si](C)(C)C)[Si](C)(C)C)=N2)CC1	3256.1	Standard non polar	33892256
Sipatrigine,2TMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N([Si](C)(C)C)[Si](C)(C)C)=N2)CC1	3801.5	Standard polar	33892256
Sipatrigine,1TBDMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N[Si](C)(C)C(C)(C)C)=N2)CC1	3185.1	Semi standard non polar	33892256
Sipatrigine,1TBDMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N[Si](C)(C)C(C)(C)C)=N2)CC1	3430.1	Standard non polar	33892256
Sipatrigine,1TBDMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N[Si](C)(C)C(C)(C)C)=N2)CC1	4083.8	Standard polar	33892256
Sipatrigine,2TBDMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)CC1	3263.9	Semi standard non polar	33892256
Sipatrigine,2TBDMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)CC1	3767.0	Standard non polar	33892256
Sipatrigine,2TBDMS,isomer #1	CN1CCN(C2=NC=C(C3=CC(Cl)=CC(Cl)=C3Cl)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N2)CC1	3847.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sipatrigine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abi-5009000000-c9b2258393a128ae7ef1	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sipatrigine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54793

KEGG Compound ID

C13852

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60803

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 Sipatrigine (HMDB0258307)

MOL for HMDB0258307 (Sipatrigine)

3D MOL for HMDB0258307 (Sipatrigine)

3D SDF for HMDB0258307 (Sipatrigine)

3D-SDF for HMDB0258307 (Sipatrigine)

PDB for HMDB0258307 (Sipatrigine)

3D PDB for HMDB0258307 (Sipatrigine)

SMILES for HMDB0258307 (Sipatrigine)

INCHI for HMDB0258307 (Sipatrigine)

Structure for HMDB0258307 (Sipatrigine)

3D Structure for HMDB0258307 (Sipatrigine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra