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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:07:29 UTC

Update Date

2021-09-26 23:12:23 UTC

HMDB ID

HMDB0256601

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pirinixic acid

Description

2-Methylthioribosyl-trans-zeatin, also known as wy-14,643, belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group. 2-Methylthioribosyl-trans-zeatin has been detected, but not quantified in, common peas (Pisum sativum) and common wheats (Triticum aestivum). This could make 2-methylthioribosyl-trans-zeatin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Methylthioribosyl-trans-zeatin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pirinixic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pirinixic acid 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

HMDB0256601
     RDKit          3D
Pirinixic acid
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.4205    0.4644    0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0276   -0.0340    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7513   -1.1646    1.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -1.6409    1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4380   -0.9669    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792    0.1712   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894    0.8832   -0.7200 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6763    0.6170   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4803    1.4748   -1.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8385    1.2778   -1.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974    2.4027   -2.6802 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    0.2356   -1.1086 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6712   -0.5919   -0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4083   -1.9948    0.4414 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703   -2.1015    0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9244   -0.9842    0.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1268    0.0675    0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4018   -1.0846    2.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489   -0.3982   -0.2473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9932    0.5993   -0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3450    1.8065   -0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9779   -0.0031    1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509    0.1753   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4938    1.5530    0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5510   -1.6955    1.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515   -2.5325    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482   -1.3702    0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    1.7482   -1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0700    2.3265   -2.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5377   -3.0514    0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460   -2.1229   -0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5123   -0.3071    2.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373    2.6917   -0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365    1.9298   -0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9587    1.6198   -1.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  2  0
  6 20  2  0
 20 21  1  0
 20  2  1  0
 19  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  9 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END


  Mrv0541 02241221302D          

 21 22  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 S   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  4  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
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 20  1  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256601

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C)C(NC2=CC(Cl)=NC(SCC(O)=O)=N2)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14ClN3O2S/c1-8-4-3-5-10(9(8)2)16-12-6-11(15)17-14(18-12)21-7-13(19)20/h3-6H,7H2,1-2H3,(H,19,20)(H,16,17,18)

> <INCHI_KEY>
SZRPDCCEHVWOJX-UHFFFAOYSA-N

> <FORMULA>
C14H14ClN3O2S

> <MOLECULAR_WEIGHT>
323.798

> <EXACT_MASS>
323.049525104

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.072586675753314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-({4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl}sulfanyl)acetic acid

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
4.107006531805247

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.969580694379392

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2456353039330246

> <JCHEM_PKA_STRONGEST_BASIC>
2.0152231208507883

> <JCHEM_POLAR_SURFACE_AREA>
75.11

> <JCHEM_REFRACTIVITY>
86.40759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pirinixic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256601
     RDKit          3D
Pirinixic acid
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.4205    0.4644    0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0276   -0.0340    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7513   -1.1646    1.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -1.6409    1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4380   -0.9669    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792    0.1712   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894    0.8832   -0.7200 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6763    0.6170   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4803    1.4748   -1.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8385    1.2778   -1.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974    2.4027   -2.6802 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    0.2356   -1.1086 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6712   -0.5919   -0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4083   -1.9948    0.4414 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703   -2.1015    0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9244   -0.9842    0.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1268    0.0675    0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4018   -1.0846    2.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489   -0.3982   -0.2473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9932    0.5993   -0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3450    1.8065   -0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9779   -0.0031    1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509    0.1753   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4938    1.5530    0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5510   -1.6955    1.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515   -2.5325    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482   -1.3702    0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    1.7482   -1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0700    2.3265   -2.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5377   -3.0514    0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460   -2.1229   -0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5123   -0.3071    2.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373    2.6917   -0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365    1.9298   -0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9587    1.6198   -1.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  2  0
  6 20  2  0
 20 21  1  0
 20  2  1  0
 19  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  9 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.668 -10.010   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.335  -7.700   0.000  0.00  0.00           N+0
HETATM   15  S   UNK     0       4.001 -10.010   0.000  0.00  0.00           S+0
HETATM   16  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   20 Cl   UNK     0       9.336 -10.010   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    4    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   11                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0256601
HETATM    1  C1  UNL     1      -5.420   0.464   0.533  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.028  -0.034   0.593  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.751  -1.165   1.322  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.468  -1.641   1.392  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.438  -0.967   0.714  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.679   0.171  -0.028  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.689   0.883  -0.720  1.00  0.00           N  
HETATM    8  C7  UNL     1       0.676   0.617  -0.813  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.480   1.475  -1.570  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.838   1.278  -1.708  1.00  0.00           C  
HETATM   11 CL1  UNL     1       3.797   2.403  -2.680  1.00  0.00          CL  
HETATM   12  N2  UNL     1       3.440   0.236  -1.109  1.00  0.00           N  
HETATM   13  C10 UNL     1       2.671  -0.592  -0.381  1.00  0.00           C  
HETATM   14  S1  UNL     1       3.408  -1.995   0.441  1.00  0.00           S  
HETATM   15  C11 UNL     1       5.170  -2.101   0.163  1.00  0.00           C  
HETATM   16  C12 UNL     1       5.924  -0.984   0.778  1.00  0.00           C  
HETATM   17  O1  UNL     1       6.127   0.067   0.117  1.00  0.00           O  
HETATM   18  O2  UNL     1       6.402  -1.085   2.055  1.00  0.00           O  
HETATM   19  N3  UNL     1       1.349  -0.398  -0.247  1.00  0.00           N  
HETATM   20  C13 UNL     1      -2.993   0.599  -0.058  1.00  0.00           C  
HETATM   21  C14 UNL     1      -3.345   1.807  -0.831  1.00  0.00           C  
HETATM   22  H1  UNL     1      -5.978  -0.003   1.376  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.951   0.175  -0.398  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.494   1.553   0.715  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.551  -1.696   1.854  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.252  -2.533   1.967  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.448  -1.370   0.793  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.032   1.748  -1.246  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.070   2.326  -2.076  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.538  -3.051   0.574  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.346  -2.123  -0.932  1.00  0.00           H  
HETATM   32  H11 UNL     1       6.512  -0.307   2.705  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.837   2.692  -0.445  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.436   1.930  -0.976  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.959   1.620  -1.877  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   20
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   27
CONECT    6    7   20   20
CONECT    7    8   28
CONECT    8    9    9   19
CONECT    9   10   29
CONECT   10   11   12   12
CONECT   12   13
CONECT   13   14   19   19
CONECT   14   15
CONECT   15   16   30   31
CONECT   16   17   17   18
CONECT   18   32
CONECT   20   21
CONECT   21   33   34   35
END

HMDB0256601
     RDKit          3D
Pirinixic acid
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.4205    0.4644    0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0276   -0.0340    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7513   -1.1646    1.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -1.6409    1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4380   -0.9669    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792    0.1712   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894    0.8832   -0.7200 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6763    0.6170   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4803    1.4748   -1.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8385    1.2778   -1.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974    2.4027   -2.6802 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    0.2356   -1.1086 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6712   -0.5919   -0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4083   -1.9948    0.4414 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703   -2.1015    0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9244   -0.9842    0.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1268    0.0675    0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4018   -1.0846    2.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3489   -0.3982   -0.2473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9932    0.5993   -0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3450    1.8065   -0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9779   -0.0031    1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509    0.1753   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4938    1.5530    0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5510   -1.6955    1.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515   -2.5325    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482   -1.3702    0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    1.7482   -1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0700    2.3265   -2.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5377   -3.0514    0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460   -2.1229   -0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5123   -0.3071    2.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373    2.6917   -0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365    1.9298   -0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9587    1.6198   -1.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 13 19  2  0
  6 20  2  0
 20 21  1  0
 20  2  1  0
 19  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  9 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
((4-Chloro-6-((2,3-dimethylphenyl)amino)-2-pyrimidinyl)thio)acetic acid	ChEBI
(4-Chloro-6-(2,3-xylidino)-2-pyrimidinylthio)acetic acid	ChEBI
WY-14,643	ChEBI
((4-Chloro-6-((2,3-dimethylphenyl)amino)-2-pyrimidinyl)thio)acetate	Generator
(4-Chloro-6-(2,3-xylidino)-2-pyrimidinylthio)acetate	Generator
Pirinixate	Generator
Wyeth-14643	MeSH
4-Chloro-6-(2,3-xylidinyl)-2-pyrimidinylthioacetic acid	MeSH
Wyeth 14,643	MeSH
4-Chloro-6-(2,3-dimethylphenyl)amino-2-pyrimidinylthioacetic acid	MeSH
CXPTA	MeSH

Chemical Formula

C₁₄H₁₄ClN₃O₂S

Average Molecular Weight

323.798

Monoisotopic Molecular Weight

323.049525104

IUPAC Name

2-({4-chloro-6-[(2,3-dimethylphenyl)amino]pyrimidin-2-yl}sulfanyl)acetic acid

Traditional Name

pirinixic acid

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(NC2=CC(Cl)=NC(SCC(O)=O)=N2)=CC=C1

InChI Identifier

InChI=1S/C14H14ClN3O2S/c1-8-4-3-5-10(9(8)2)16-12-6-11(15)17-14(18-12)21-7-13(19)20/h3-6H,7H2,1-2H3,(H,19,20)(H,16,17,18)

InChI Key

SZRPDCCEHVWOJX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Aryl thioethers

Direct Parent

Aryl thioethers

Alternative Parents

Substituents

Aryl thioether
O-xylene
Xylene
Halopyrimidine
Alkylarylthioether
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Hydropyrimidine
Pyrimidine
Benzenoid
Imidolactam
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Sulfenyl compound
Organoheterocyclic compound
Organohalogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aryl sulfide (CHEBI:32509 )
organochlorine compound (CHEBI:32509 )
pyrimidines (CHEBI:32509 )

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	3.79	ALOGPS
logP	4.11	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.25	ChemAxon
pKa (Strongest Basic)	2.02	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.41 m³·mol⁻¹	ChemAxon
Polarizability	32.07 Å³	ChemAxon
Number of Rings	2	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]+	172.184	30932474
DeepCCS	[M-H]-	169.826	30932474
DeepCCS	[M-2H]-	203.364	30932474
DeepCCS	[M+Na]+	178.922	30932474
AllCCS	[M+H]+	170.0	32859911
AllCCS	[M+H-H2O]+	166.8	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	173.8	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	167.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.83 minutes	32390414
Predicted by Siyang on May 30, 2022	14.923 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2235.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	410.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	242.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	100.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	721.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	691.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1302.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	470.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1514.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	380.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	443.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	297.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	356.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	92.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pirinixic acid	CC1=C(C)C(NC2=CC(Cl)=NC(SCC(O)=O)=N2)=CC=C1	4328.4	Standard polar	33892256
Pirinixic acid	CC1=C(C)C(NC2=CC(Cl)=NC(SCC(O)=O)=N2)=CC=C1	2774.7	Standard non polar	33892256
Pirinixic acid	CC1=C(C)C(NC2=CC(Cl)=NC(SCC(O)=O)=N2)=CC=C1	2927.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pirinixic acid,2TMS,isomer #1	CC1=CC=CC(N(C2=CC(Cl)=NC(SCC(=O)O[Si](C)(C)C)=N2)[Si](C)(C)C)=C1C	2676.6	Semi standard non polar	33892256
Pirinixic acid,2TMS,isomer #1	CC1=CC=CC(N(C2=CC(Cl)=NC(SCC(=O)O[Si](C)(C)C)=N2)[Si](C)(C)C)=C1C	2462.7	Standard non polar	33892256
Pirinixic acid,2TMS,isomer #1	CC1=CC=CC(N(C2=CC(Cl)=NC(SCC(=O)O[Si](C)(C)C)=N2)[Si](C)(C)C)=C1C	3284.3	Standard polar	33892256
Pirinixic acid,2TBDMS,isomer #1	CC1=CC=CC(N(C2=CC(Cl)=NC(SCC(=O)O[Si](C)(C)C(C)(C)C)=N2)[Si](C)(C)C(C)(C)C)=C1C	3124.9	Semi standard non polar	33892256
Pirinixic acid,2TBDMS,isomer #1	CC1=CC=CC(N(C2=CC(Cl)=NC(SCC(=O)O[Si](C)(C)C(C)(C)C)=N2)[Si](C)(C)C(C)(C)C)=C1C	2856.2	Standard non polar	33892256
Pirinixic acid,2TBDMS,isomer #1	CC1=CC=CC(N(C2=CC(Cl)=NC(SCC(=O)O[Si](C)(C)C(C)(C)C)=N2)[Si](C)(C)C(C)(C)C)=C1C	3438.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pirinixic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ec-3493000000-41254128b0b7ef61359c	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pirinixic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pirinixic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pirinixic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pirinixic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pirinixic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 15V, Positive-QTOF	splash10-00di-0009000000-df13940b64a70e0a054d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 30V, Positive-QTOF	splash10-056r-0096000000-88655a739725484f17b8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 60V, Positive-QTOF	splash10-066r-1890000000-3dc38262a79bb0463bdf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 45V, Positive-QTOF	splash10-016r-0090000000-e388fdded8fee3046fb0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 15V, Negative-QTOF	splash10-004i-0090000000-f25a19c3657003477bb1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 60V, Positive-QTOF	splash10-014i-1890000000-ada3fdf4b422026e5df1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 30V, Negative-QTOF	splash10-004i-0090000000-0025e33da6dcfaed522a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 90V, Positive-QTOF	splash10-0a6r-3900000000-521a86a7cd0cae1d9f42	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 75V, Positive-QTOF	splash10-0a4i-2910000000-00be1de0db00823c1a6f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 60V, Negative-QTOF	splash10-014i-9420000000-68e10eaa7084fe7f1969	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 75V, Negative-QTOF	splash10-014i-9200000000-fb6a4e0504435974590c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 90V, Negative-QTOF	splash10-014i-9100000000-653134d04ba0e80c24b8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 45V, Negative-QTOF	splash10-00or-5490000000-d634a5d35d085f2f2162	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 75V, Positive-QTOF	splash10-0a4i-2910000000-9ae6557c22832904a69b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pirinixic acid 30V, Positive-QTOF	splash10-056r-0096000000-beaab42afa1799ec466c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirinixic acid 10V, Positive-QTOF	splash10-00di-4139000000-505b4b418d99c593c3bd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirinixic acid 20V, Positive-QTOF	splash10-05gl-3394000000-ac6924800564aa944ddd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirinixic acid 40V, Positive-QTOF	splash10-0a4i-6940000000-f079a5859fa416b10a4a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirinixic acid 10V, Negative-QTOF	splash10-00di-0098000000-53eb02de2a49fde45996	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirinixic acid 20V, Negative-QTOF	splash10-0006-9262000000-37ae087fb61042ad74fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirinixic acid 40V, Negative-QTOF	splash10-0gb9-5940000000-62e944b3e06fefb81efc	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pirinixic_Acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

32509

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 Pirinixic acid (HMDB0256601)

MOL for HMDB0256601 (Pirinixic acid)

3D MOL for HMDB0256601 (Pirinixic acid)

3D SDF for HMDB0256601 (Pirinixic acid)

3D-SDF for HMDB0256601 (Pirinixic acid)

PDB for HMDB0256601 (Pirinixic acid)

3D PDB for HMDB0256601 (Pirinixic acid)

SMILES for HMDB0256601 (Pirinixic acid)

INCHI for HMDB0256601 (Pirinixic acid)

Structure for HMDB0256601 (Pirinixic acid)

3D Structure for HMDB0256601 (Pirinixic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra