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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:50 UTC

Update Date

2022-09-22 18:35:07 UTC

HMDB ID

HMDB0002377

Secondary Accession Numbers

HMDB02377

Metabolite Identification

Common Name

Urothion

Description

Urothion belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. Urothion has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make urothion a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Urothion.

Structure

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

HMDB0002377
     RDKit          3D
Urothion
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.0437   -3.2711   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9653   -2.0562    1.0262 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3237   -0.4603    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2152    0.4741   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7184    0.3863   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9726   -0.3080   -1.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2965    1.7753   -0.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1227    2.5610    0.8620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2218    1.7639   -0.5500 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015    1.0872   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    1.5369   -0.3605 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6252    0.7557   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    1.1469   -0.1448 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9269    0.3642    0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2541    0.8150    0.0246 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307   -0.8492    0.7124 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3823   -1.2864    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510   -2.4210    1.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079   -0.4668    0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0657   -0.9264    0.6698 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048   -0.1337    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0552   -3.5826   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178   -4.1925    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4809   -2.9605   -1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0547   -0.1327    0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8690    0.3434   -2.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7312    2.2798   -1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3475    1.6701   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846    2.0482    1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0895    2.0871   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4980    1.8255    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0192    0.1268   -0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 21 10  1  0
 19 12  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
M  END


  Mrv0541 02231219312D          

 21 23  0  0  0  0            999 V2000
   22.3696   -9.9362    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.1133  -12.0483    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.8323  -10.6698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6573  -12.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1756   -9.7058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7057  -12.2293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1661  -12.2379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4186  -10.9547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6182  -12.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6182  -10.5594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4198  -11.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8323  -12.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8186   -9.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4186  -11.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3326  -11.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1661  -10.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9036  -11.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5947  -11.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1133  -10.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9036  -10.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3326  -10.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 19  1  0  0  0  0
  2 15  1  0  0  0  0
  2 18  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5 16  2  0  0  0  0
  6 14  1  0  0  0  0
  7 14  1  0  0  0  0
  7 17  1  0  0  0  0
  8 14  2  0  0  0  0
  8 16  1  0  0  0  0
  9 15  1  0  0  0  0
  9 17  2  0  0  0  0
 10 20  2  0  0  0  0
 10 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 18  1  0  0  0  0
 15 21  2  0  0  0  0
 16 20  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002377

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC1=C(SC2=C1N=C1C(=O)N=C(N)NC1=N2)C(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C11H11N5O3S2/c1-20-7-4-10(21-6(7)3(18)2-17)14-8-5(13-4)9(19)16-11(12)15-8/h3,17-18H,2H2,1H3,(H3,12,14,15,16,19)

> <INCHI_KEY>
RPUOVNROVSNPBD-UHFFFAOYSA-N

> <FORMULA>
C11H11N5O3S2

> <MOLECULAR_WEIGHT>
325.367

> <EXACT_MASS>
325.030330623

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
31.25276121688511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-7-(1,2-dihydroxyethyl)-6-(methylsulfanyl)-1H,4H-thieno[3,2-g]pteridin-4-one

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
0.5519444626666672

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.854046499490654

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.608169352487551

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3420399853388658

> <JCHEM_POLAR_SURFACE_AREA>
133.72

> <JCHEM_REFRACTIVITY>
79.6251

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-7-(1,2-dihydroxyethyl)-6-(methylsulfanyl)-1H-thieno[3,2-g]pteridin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002377
     RDKit          3D
Urothion
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.0437   -3.2711   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9653   -2.0562    1.0262 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3237   -0.4603    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2152    0.4741   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7184    0.3863   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9726   -0.3080   -1.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2965    1.7753   -0.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1227    2.5610    0.8620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2218    1.7639   -0.5500 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015    1.0872   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    1.5369   -0.3605 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6252    0.7557   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    1.1469   -0.1448 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9269    0.3642    0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2541    0.8150    0.0246 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307   -0.8492    0.7124 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3823   -1.2864    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510   -2.4210    1.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079   -0.4668    0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0657   -0.9264    0.6698 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048   -0.1337    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0552   -3.5826   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178   -4.1925    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4809   -2.9605   -1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0547   -0.1327    0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8690    0.3434   -2.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7312    2.2798   -1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3475    1.6701   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846    2.0482    1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0895    2.0871   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4980    1.8255    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0192    0.1268   -0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 21 10  1  0
 19 12  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      41.757 -18.548   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      41.278 -22.490   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      44.487 -19.917   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      46.027 -22.584   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      35.794 -18.117   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      33.051 -22.828   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      35.777 -22.844   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      34.381 -20.449   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      38.487 -22.791   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      38.487 -19.711   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      43.717 -21.251   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      44.487 -22.584   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.728 -17.401   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.381 -22.053   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.821 -22.021   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      35.777 -19.657   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.153 -22.021   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      42.177 -21.251   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.278 -20.011   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.153 -20.481   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.821 -20.481   0.000  0.00  0.00           C+0
CONECT    1   13   19                                                       
CONECT    2   15   18                                                       
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   16                                                            
CONECT    6   14                                                            
CONECT    7   14   17                                                       
CONECT    8   14   16                                                       
CONECT    9   15   17                                                       
CONECT   10   20   21                                                       
CONECT   11    3   12   18                                                  
CONECT   12    4   11                                                       
CONECT   13    1                                                            
CONECT   14    6    7    8                                                  
CONECT   15    2    9   21                                                  
CONECT   16    5    8   20                                                  
CONECT   17    7    9   20                                                  
CONECT   18    2   11   19                                                  
CONECT   19    1   18   21                                                  
CONECT   20   10   16   17                                                  
CONECT   21   10   15   19                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0002377
HETATM    1  C1  UNL     1      -2.044  -3.271  -0.314  1.00  0.00           C  
HETATM    2  S1  UNL     1      -1.965  -2.056   1.026  1.00  0.00           S  
HETATM    3  C2  UNL     1      -1.324  -0.460   0.393  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.215   0.474  -0.038  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.718   0.386  -0.088  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.973  -0.308  -1.301  1.00  0.00           O  
HETATM    7  C5  UNL     1      -4.297   1.775  -0.276  1.00  0.00           C  
HETATM    8  O2  UNL     1      -4.123   2.561   0.862  1.00  0.00           O  
HETATM    9  S2  UNL     1      -1.222   1.764  -0.550  1.00  0.00           S  
HETATM   10  C6  UNL     1       0.301   1.087  -0.204  1.00  0.00           C  
HETATM   11  N1  UNL     1       1.584   1.537  -0.360  1.00  0.00           N  
HETATM   12  C7  UNL     1       2.625   0.756  -0.002  1.00  0.00           C  
HETATM   13  N2  UNL     1       3.889   1.147  -0.145  1.00  0.00           N  
HETATM   14  C8  UNL     1       4.927   0.364   0.203  1.00  0.00           C  
HETATM   15  N3  UNL     1       6.254   0.815   0.025  1.00  0.00           N  
HETATM   16  N4  UNL     1       4.631  -0.849   0.712  1.00  0.00           N  
HETATM   17  C9  UNL     1       3.382  -1.286   0.875  1.00  0.00           C  
HETATM   18  O3  UNL     1       3.151  -2.421   1.350  1.00  0.00           O  
HETATM   19  C10 UNL     1       2.308  -0.467   0.508  1.00  0.00           C  
HETATM   20  N5  UNL     1       1.066  -0.926   0.670  1.00  0.00           N  
HETATM   21  C11 UNL     1      -0.005  -0.134   0.304  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.055  -3.583  -0.590  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.518  -4.193   0.088  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.481  -2.960  -1.223  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.055  -0.133   0.787  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.869   0.343  -2.063  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.731   2.280  -1.104  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.348   1.670  -0.554  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.785   2.048   1.638  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.090   2.087  -0.539  1.00  0.00           H  
HETATM   31  H10 UNL     1       6.498   1.826   0.048  1.00  0.00           H  
HETATM   32  H11 UNL     1       7.019   0.127  -0.138  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5    9
CONECT    5    6    7   25
CONECT    6   26
CONECT    7    8   27   28
CONECT    8   29
CONECT    9   10
CONECT   10   11   11   21
CONECT   11   12
CONECT   12   13   19   19
CONECT   13   14   30
CONECT   14   15   16   16
CONECT   15   31   32
CONECT   16   17
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   21
END

HMDB0002377
     RDKit          3D
Urothion
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.0437   -3.2711   -0.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9653   -2.0562    1.0262 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3237   -0.4603    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2152    0.4741   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7184    0.3863   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9726   -0.3080   -1.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2965    1.7753   -0.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1227    2.5610    0.8620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2218    1.7639   -0.5500 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015    1.0872   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    1.5369   -0.3605 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6252    0.7557   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    1.1469   -0.1448 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9269    0.3642    0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2541    0.8150    0.0246 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307   -0.8492    0.7124 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3823   -1.2864    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510   -2.4210    1.3499 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079   -0.4668    0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0657   -0.9264    0.6698 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048   -0.1337    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0552   -3.5826   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178   -4.1925    0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4809   -2.9605   -1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0547   -0.1327    0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8690    0.3434   -2.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7312    2.2798   -1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3475    1.6701   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846    2.0482    1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0895    2.0871   -0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4980    1.8255    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0192    0.1268   -0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 21 10  1  0
 19 12  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-(8CI)-2-amino-7-(1,2-dihydroxyethyl)-6-(methylthio)-thieno[3,2-g]pteridin-4(1H)-one	HMDB
Urothione	HMDB, MeSH
2-amino-7-(1,2-Dihydroxyethyl)-6-(methylthio)thieno(3,2-g)pteridin-4(3H)one	MeSH, HMDB
1-[4-Hydroxy-2-imino-6-(methylsulphanyl)-1H,2H-thieno[3,2-g]pteridin-7-yl]ethane-1,2-diol	Generator, HMDB
Urothion	MeSH

Chemical Formula

C₁₁H₁₁N₅O₃S₂

Average Molecular Weight

325.367

Monoisotopic Molecular Weight

325.030330623

IUPAC Name

2-amino-7-(1,2-dihydroxyethyl)-6-(methylsulfanyl)-1H,4H-thieno[3,2-g]pteridin-4-one

Traditional Name

2-amino-7-(1,2-dihydroxyethyl)-6-(methylsulfanyl)-1H-thieno[3,2-g]pteridin-4-one

CAS Registry Number

19295-31-9

SMILES

CSC1=C(SC2=C1N=C1C(=O)N=C(N)NC1=N2)C(O)CO

InChI Identifier

InChI=1S/C11H11N5O3S2/c1-20-7-4-10(21-6(7)3(18)2-17)14-8-5(13-4)9(19)16-11(12)15-8/h3,17-18H,2H2,1H3,(H3,12,14,15,16,19)

InChI Key

RPUOVNROVSNPBD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Pterins and derivatives

Alternative Parents

Substituents

Pterin
Aryl thioether
Aminopyrimidine
Pyrimidone
Alkylarylthioether
Pyrazine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Thiophene
1,2-diol
Secondary alcohol
Azacycle
Sulfenyl compound
Thioether
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Amine
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0002377)

Source

Endogenous

Endogenous (HMDB: HMDB0002377)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	> 360 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.1 mg/mL at pH 6.6	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	0.09	ALOGPS
logP	0.55	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.61	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.63 m³·mol⁻¹	ChemAxon
Polarizability	31.25 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
DarkChem	[M+H]+	170.632	31661259
DarkChem	[M-H]-	171.976	31661259
DeepCCS	[M+H]+	175.144	30932474
DeepCCS	[M-H]-	172.786	30932474
DeepCCS	[M-2H]-	205.751	30932474
DeepCCS	[M+Na]+	181.237	30932474
AllCCS	[M+H]+	169.1	32859911
AllCCS	[M+H-H2O]+	166.0	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.8	32859911
AllCCS	[M-H]-	168.9	32859911
AllCCS	[M+Na-2H]-	168.6	32859911
AllCCS	[M+HCOO]-	168.4	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.	2.44 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3022 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.96 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	917.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	238.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	84.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	341.3 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	388.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	230.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	689.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	196.3 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	915.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	218.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	222.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	402.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	233.0 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	122.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Urothion	CSC1=C(SC2=C1N=C1C(=O)N=C(N)NC1=N2)C(O)CO	4001.8	Standard polar	33892256
Urothion	CSC1=C(SC2=C1N=C1C(=O)N=C(N)NC1=N2)C(O)CO	2963.5	Standard non polar	33892256
Urothion	CSC1=C(SC2=C1N=C1C(=O)N=C(N)NC1=N2)C(O)CO	3656.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Urothion,1TMS,isomer #1	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)[NH]3	3243.2	Semi standard non polar	33892256
Urothion,1TMS,isomer #2	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)[NH]3	3238.6	Semi standard non polar	33892256
Urothion,1TMS,isomer #3	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)[NH]3	3231.4	Semi standard non polar	33892256
Urothion,1TMS,isomer #4	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C	3217.8	Semi standard non polar	33892256
Urothion,2TMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)[NH]3	3177.8	Semi standard non polar	33892256
Urothion,2TMS,isomer #2	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)[NH]3	3129.5	Semi standard non polar	33892256
Urothion,2TMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C	3180.2	Semi standard non polar	33892256
Urothion,2TMS,isomer #4	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)[NH]3	3113.0	Semi standard non polar	33892256
Urothion,2TMS,isomer #5	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C	3159.2	Semi standard non polar	33892256
Urothion,2TMS,isomer #6	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)N3[Si](C)(C)C	3121.2	Semi standard non polar	33892256
Urothion,2TMS,isomer #7	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]3	3103.8	Semi standard non polar	33892256
Urothion,3TMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)[NH]3	3099.5	Semi standard non polar	33892256
Urothion,3TMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)[NH]3	3546.9	Standard non polar	33892256
Urothion,3TMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)[NH]3	4450.6	Standard polar	33892256
Urothion,3TMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C	3138.3	Semi standard non polar	33892256
Urothion,3TMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C	3474.8	Standard non polar	33892256
Urothion,3TMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C	4563.2	Standard polar	33892256
Urothion,3TMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)N3[Si](C)(C)C	3155.6	Semi standard non polar	33892256
Urothion,3TMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)N3[Si](C)(C)C	3561.1	Standard non polar	33892256
Urothion,3TMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)N3[Si](C)(C)C	4368.3	Standard polar	33892256
Urothion,3TMS,isomer #4	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]3	3112.5	Semi standard non polar	33892256
Urothion,3TMS,isomer #4	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]3	3595.3	Standard non polar	33892256
Urothion,3TMS,isomer #4	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]3	4292.4	Standard polar	33892256
Urothion,3TMS,isomer #5	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)N3[Si](C)(C)C	3107.4	Semi standard non polar	33892256
Urothion,3TMS,isomer #5	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)N3[Si](C)(C)C	3523.5	Standard non polar	33892256
Urothion,3TMS,isomer #5	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)N3[Si](C)(C)C	4333.1	Standard polar	33892256
Urothion,3TMS,isomer #6	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]3	3077.9	Semi standard non polar	33892256
Urothion,3TMS,isomer #6	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]3	3555.0	Standard non polar	33892256
Urothion,3TMS,isomer #6	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]3	4254.6	Standard polar	33892256
Urothion,3TMS,isomer #7	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3124.3	Semi standard non polar	33892256
Urothion,3TMS,isomer #7	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3605.6	Standard non polar	33892256
Urothion,3TMS,isomer #7	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	4308.4	Standard polar	33892256
Urothion,4TMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)N3[Si](C)(C)C	3140.9	Semi standard non polar	33892256
Urothion,4TMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)N3[Si](C)(C)C	3569.0	Standard non polar	33892256
Urothion,4TMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C)N3[Si](C)(C)C	4048.4	Standard polar	33892256
Urothion,4TMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]3	3117.3	Semi standard non polar	33892256
Urothion,4TMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]3	3626.0	Standard non polar	33892256
Urothion,4TMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]3	3976.8	Standard polar	33892256
Urothion,4TMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3163.7	Semi standard non polar	33892256
Urothion,4TMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3673.0	Standard non polar	33892256
Urothion,4TMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3910.5	Standard polar	33892256
Urothion,4TMS,isomer #4	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3121.0	Semi standard non polar	33892256
Urothion,4TMS,isomer #4	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3652.1	Standard non polar	33892256
Urothion,4TMS,isomer #4	CSC1=C(C(O)CO[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3877.9	Standard polar	33892256
Urothion,5TMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3176.5	Semi standard non polar	33892256
Urothion,5TMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3663.0	Standard non polar	33892256
Urothion,5TMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C)O[Si](C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N3[Si](C)(C)C	3673.5	Standard polar	33892256
Urothion,1TBDMS,isomer #1	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)[NH]3	3482.8	Semi standard non polar	33892256
Urothion,1TBDMS,isomer #2	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)[NH]3	3444.0	Semi standard non polar	33892256
Urothion,1TBDMS,isomer #3	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]3	3406.6	Semi standard non polar	33892256
Urothion,1TBDMS,isomer #4	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C(C)(C)C	3423.5	Semi standard non polar	33892256
Urothion,2TBDMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)[NH]3	3538.5	Semi standard non polar	33892256
Urothion,2TBDMS,isomer #2	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]3	3449.1	Semi standard non polar	33892256
Urothion,2TBDMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C(C)(C)C	3515.2	Semi standard non polar	33892256
Urothion,2TBDMS,isomer #4	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]3	3419.3	Semi standard non polar	33892256
Urothion,2TBDMS,isomer #5	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C(C)(C)C	3492.3	Semi standard non polar	33892256
Urothion,2TBDMS,isomer #6	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	3512.8	Semi standard non polar	33892256
Urothion,2TBDMS,isomer #7	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]3	3487.1	Semi standard non polar	33892256
Urothion,3TBDMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]3	3596.3	Semi standard non polar	33892256
Urothion,3TBDMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]3	4192.7	Standard non polar	33892256
Urothion,3TBDMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]3	4453.0	Standard polar	33892256
Urothion,3TBDMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C(C)(C)C	3633.0	Semi standard non polar	33892256
Urothion,3TBDMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C(C)(C)C	4124.9	Standard non polar	33892256
Urothion,3TBDMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N)N3[Si](C)(C)C(C)(C)C	4527.5	Standard polar	33892256
Urothion,3TBDMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	3635.4	Semi standard non polar	33892256
Urothion,3TBDMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4197.6	Standard non polar	33892256
Urothion,3TBDMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4319.4	Standard polar	33892256
Urothion,3TBDMS,isomer #4	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]3	3562.2	Semi standard non polar	33892256
Urothion,3TBDMS,isomer #4	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]3	4224.9	Standard non polar	33892256
Urothion,3TBDMS,isomer #4	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]3	4275.9	Standard polar	33892256
Urothion,3TBDMS,isomer #5	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	3625.4	Semi standard non polar	33892256
Urothion,3TBDMS,isomer #5	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4169.3	Standard non polar	33892256
Urothion,3TBDMS,isomer #5	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4300.5	Standard polar	33892256
Urothion,3TBDMS,isomer #6	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]3	3556.0	Semi standard non polar	33892256
Urothion,3TBDMS,isomer #6	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]3	4185.5	Standard non polar	33892256
Urothion,3TBDMS,isomer #6	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]3	4256.2	Standard polar	33892256
Urothion,3TBDMS,isomer #7	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	3632.7	Semi standard non polar	33892256
Urothion,3TBDMS,isomer #7	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4169.7	Standard non polar	33892256
Urothion,3TBDMS,isomer #7	CSC1=C(C(O)CO)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4233.1	Standard polar	33892256
Urothion,4TBDMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	3827.1	Semi standard non polar	33892256
Urothion,4TBDMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4382.1	Standard non polar	33892256
Urothion,4TBDMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4173.2	Standard polar	33892256
Urothion,4TBDMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]3	3740.5	Semi standard non polar	33892256
Urothion,4TBDMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]3	4415.8	Standard non polar	33892256
Urothion,4TBDMS,isomer #2	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]3	4122.3	Standard polar	33892256
Urothion,4TBDMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	3796.0	Semi standard non polar	33892256
Urothion,4TBDMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4396.4	Standard non polar	33892256
Urothion,4TBDMS,isomer #3	CSC1=C(C(CO)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4056.1	Standard polar	33892256
Urothion,4TBDMS,isomer #4	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	3781.8	Semi standard non polar	33892256
Urothion,4TBDMS,isomer #4	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4383.6	Standard non polar	33892256
Urothion,4TBDMS,isomer #4	CSC1=C(C(O)CO[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4043.4	Standard polar	33892256
Urothion,5TBDMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	3972.8	Semi standard non polar	33892256
Urothion,5TBDMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	4532.5	Standard non polar	33892256
Urothion,5TBDMS,isomer #1	CSC1=C(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)SC2=NC3=C(N=C12)C(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C	3962.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Urothion GC-MS (Non-derivatized) - 70eV, Positive	splash10-055g-3191000000-bb188a9be9d62c01a25a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Urothion GC-MS (2 TMS) - 70eV, Positive	splash10-0udi-9318600000-6aff9fb2d196d9c6cbf1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Urothion GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Urothion 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 - Urothion 10V, Positive-QTOF	splash10-004i-0029000000-15e9975d010dbe4ee4d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 20V, Positive-QTOF	splash10-0bvi-1069000000-b60fd516f2b0f363cef3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 40V, Positive-QTOF	splash10-03kc-1190000000-10aebeaebb39082b382e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 10V, Negative-QTOF	splash10-0006-2900000000-36d96cb87ccd49a6f80e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 20V, Negative-QTOF	splash10-0006-0980000000-a08956406f3fe53791cb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 40V, Negative-QTOF	splash10-0007-9250000000-c4d9ac25d2c15431f1bc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 10V, Positive-QTOF	splash10-004i-0009000000-15e3e7af8ab83497ffe3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 20V, Positive-QTOF	splash10-004i-0049000000-3b20347799833a4c7716	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 40V, Positive-QTOF	splash10-01za-0190000000-c58180926e03a7d1eecf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 10V, Negative-QTOF	splash10-0229-0069000000-a3698c5a1f4c10641d85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 20V, Negative-QTOF	splash10-014i-0090000000-daddc82b3cc9d646f7fc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urothion 40V, Negative-QTOF	splash10-052g-2490000000-c6eedf4737d40fdbee1f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

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

FDB022985

KNApSAcK ID

Not Available

Chemspider ID

78342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6653

PubChem Compound

86845

PDB ID

Not Available

ChEBI ID

176463

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

Bamforth FJ, Johnson JL, Davidson AG, Wong LT, Lockitch G, Applegarth DA: Biochemical investigation of a child with molybdenum cofactor deficiency. Clin Biochem. 1990 Dec;23(6):537-42. [PubMed:2289312 ]
Sakurai A, Horibe H, Kuboyama N, Hashimoto Y, Okumura Y: Determination of the absolute configuration of urothion. J Biochem. 1995 Sep;118(3):552-4. [PubMed:8690716 ]
Johnson JL, Wuebbens MM, Mandell R, Shih VE: Molybdenum cofactor deficiency in a patient previously characterized as deficient in sulfite oxidase. Biochem Med Metab Biol. 1988 Aug;40(1):86-93. [PubMed:3219233 ]
Volk M, Meyer O, Frunzke K: Metabolic relationship between the CO dehydrogenase molybdenum cofactor and the excretion of urothione by Hydrogenophaga pseudoflava. Eur J Biochem. 1994 Nov 1;225(3):1063-71. [PubMed:7957196 ]
Johnson JL, Rajagopalan KV: Structural and metabolic relationship between the molybdenum cofactor and urothione. Proc Natl Acad Sci U S A. 1982 Nov;79(22):6856-60. [PubMed:6960353 ]

Showing metabocard for Urothion (HMDB0002377)

MOL for HMDB0002377 (Urothion)

3D MOL for HMDB0002377 (Urothion)

3D SDF for HMDB0002377 (Urothion)

3D-SDF for HMDB0002377 (Urothion)

PDB for HMDB0002377 (Urothion)

3D PDB for HMDB0002377 (Urothion)

SMILES for HMDB0002377 (Urothion)

INCHI for HMDB0002377 (Urothion)

Structure for HMDB0002377 (Urothion)

3D Structure for HMDB0002377 (Urothion)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra