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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-07 09:47:23 UTC

Update Date

2021-09-26 22:50:29 UTC

HMDB ID

HMDB0242752

Secondary Accession Numbers

None

Metabolite Identification

Common Name

6-Methylthioinosine

Description

2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. 2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol is a moderately basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 6-methylthioinosine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 6-Methylthioinosine 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

HMDB0242752
     RDKit          3D
6-Methylthioinosine
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.4748    1.1285   -0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0973    0.4145    0.5242 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903    0.4241   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5041    0.9120   -1.6422 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    0.8774   -2.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2036    0.3661   -1.7147 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2304   -0.1354   -0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -0.1030    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2176   -0.6597    1.3784 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182   -1.0272    1.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -0.6991    0.3241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0591   -0.9244    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6887    0.2041   -0.5367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0362   -0.0098   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345    1.2539   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1846    0.9014   -0.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2699   -0.9062    0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608   -2.1509    0.3866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -1.0213    1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425    0.1243    2.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5670    2.1923   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4112    0.6383    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4530    0.9470   -1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2261    1.2761   -3.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5184   -1.4946    2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596   -1.7980   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448   -0.4838   -1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5846    1.7366    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7437    1.9820   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3115   -0.0813   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058   -0.4359    1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3496   -2.3463   -0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840   -1.9533    1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    0.6469    1.7069 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 19 12  1  0
 11  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv1652306031609412D          

 20 22  0  0  0  0            999 V2000
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    3.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    3.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403    2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2278    4.5972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    3.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    1.6346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0098    2.5320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  3  2  0  0  0  0
 12  9  1  0  0  0  0
 13  3  1  0  0  0  0
 13 10  2  0  0  0  0
 14  4  2  0  0  0  0
 14  6  1  0  0  0  0
 15  4  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16  2  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19  5  1  0  0  0  0
 19 11  1  0  0  0  0
 20  1  1  0  0  0  0
 20 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242752

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC1=NC=NC2=C1N=CN2C1OC(CO)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N4O4S/c1-20-10-6-9(12-3-13-10)15(4-14-6)11-8(18)7(17)5(2-16)19-11/h3-5,7-8,11,16-18H,2H2,1H3

> <INCHI_KEY>
ZDRFDHHANOYUTE-UHFFFAOYSA-N

> <FORMULA>
C11H14N4O4S

> <MOLECULAR_WEIGHT>
298.32

> <EXACT_MASS>
298.073576121

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.728878329005045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol

> <ALOGPS_LOGP>
-0.40

> <JCHEM_LOGP>
-0.6338207793333331

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.891226114724184

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.454003908770634

> <JCHEM_PKA_STRONGEST_BASIC>
2.3134589101779066

> <JCHEM_POLAR_SURFACE_AREA>
113.52000000000001

> <JCHEM_REFRACTIVITY>
71.2541

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methyl mp riboside

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242752
     RDKit          3D
6-Methylthioinosine
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.4748    1.1285   -0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0973    0.4145    0.5242 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903    0.4241   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5041    0.9120   -1.6422 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    0.8774   -2.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2036    0.3661   -1.7147 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2304   -0.1354   -0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -0.1030    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2176   -0.6597    1.3784 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182   -1.0272    1.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -0.6991    0.3241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0591   -0.9244    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6887    0.2041   -0.5367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0362   -0.0098   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345    1.2539   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1846    0.9014   -0.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2699   -0.9062    0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608   -2.1509    0.3866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -1.0213    1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425    0.1243    2.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5670    2.1923   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4112    0.6383    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4530    0.9470   -1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2261    1.2761   -3.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5184   -1.4946    2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596   -1.7980   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448   -0.4838   -1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5846    1.7366    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7437    1.9820   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3115   -0.0813   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058   -0.4359    1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3496   -2.3463   -0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840   -1.9533    1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    0.6469    1.7069 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 19 12  1  0
 11  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.322   7.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.846   5.972   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.382   5.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.382   3.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       2.292   8.581   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.136   6.402   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.136   3.051   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.752   4.726   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       6.121  -2.310   0.000  0.00  0.00           S+0
CONECT    1   20                                                            
CONECT    2    5   16                                                       
CONECT    3   12   13                                                       
CONECT    4   14   15                                                       
CONECT    5    2    7   19                                                  
CONECT    6    9   10   14                                                  
CONECT    7    5    8   17                                                  
CONECT    8    7   11   18                                                  
CONECT    9    6   12   15                                                  
CONECT   10    6   13   20                                                  
CONECT   11    8   15   19                                                  
CONECT   12    3    9                                                       
CONECT   13    3   10                                                       
CONECT   14    4    6                                                       
CONECT   15    4    9   11                                                  
CONECT   16    2                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    5   11                                                       
CONECT   20    1   10                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0242752
HETATM    1  C1  UNL     1       6.475   1.128  -0.368  1.00  0.00           C  
HETATM    2  S1  UNL     1       5.097   0.415   0.524  1.00  0.00           S  
HETATM    3  C2  UNL     1       3.590   0.424  -0.411  1.00  0.00           C  
HETATM    4  N1  UNL     1       3.504   0.912  -1.642  1.00  0.00           N  
HETATM    5  C3  UNL     1       2.314   0.877  -2.279  1.00  0.00           C  
HETATM    6  N2  UNL     1       1.204   0.366  -1.715  1.00  0.00           N  
HETATM    7  C4  UNL     1       1.230  -0.135  -0.486  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.461  -0.103   0.180  1.00  0.00           C  
HETATM    9  N3  UNL     1       2.218  -0.660   1.378  1.00  0.00           N  
HETATM   10  C6  UNL     1       0.918  -1.027   1.480  1.00  0.00           C  
HETATM   11  N4  UNL     1       0.318  -0.699   0.324  1.00  0.00           N  
HETATM   12  C7  UNL     1      -1.059  -0.924   0.036  1.00  0.00           C  
HETATM   13  O1  UNL     1      -1.689   0.204  -0.537  1.00  0.00           O  
HETATM   14  C8  UNL     1      -3.036  -0.010  -0.432  1.00  0.00           C  
HETATM   15  C9  UNL     1      -3.835   1.254  -0.210  1.00  0.00           C  
HETATM   16  O2  UNL     1      -5.185   0.901  -0.120  1.00  0.00           O  
HETATM   17  C10 UNL     1      -3.270  -0.906   0.771  1.00  0.00           C  
HETATM   18  O3  UNL     1      -3.761  -2.151   0.387  1.00  0.00           O  
HETATM   19  C11 UNL     1      -1.866  -1.021   1.338  1.00  0.00           C  
HETATM   20  O4  UNL     1      -1.643   0.124   2.096  1.00  0.00           O  
HETATM   21  H1  UNL     1       6.567   2.192  -0.108  1.00  0.00           H  
HETATM   22  H2  UNL     1       7.411   0.638   0.002  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.453   0.947  -1.460  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.226   1.276  -3.296  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.518  -1.495   2.368  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.260  -1.798  -0.587  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.445  -0.484  -1.351  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.585   1.737   0.772  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.744   1.982  -1.021  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.312  -0.081  -0.232  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.906  -0.436   1.532  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.350  -2.346  -0.511  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.684  -1.953   1.867  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.878   0.647   1.707  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5
CONECT    5    6    6   24
CONECT    6    7
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10   10
CONECT   10   11   25
CONECT   11   12
CONECT   12   13   19   26
CONECT   13   14
CONECT   14   15   17   27
CONECT   15   16   28   29
CONECT   16   30
CONECT   17   18   19   31
CONECT   18   32
CONECT   19   20   33
CONECT   20   34
END

HMDB0242752
     RDKit          3D
6-Methylthioinosine
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.4748    1.1285   -0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0973    0.4145    0.5242 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903    0.4241   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5041    0.9120   -1.6422 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    0.8774   -2.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2036    0.3661   -1.7147 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2304   -0.1354   -0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -0.1030    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2176   -0.6597    1.3784 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182   -1.0272    1.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -0.6991    0.3241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0591   -0.9244    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6887    0.2041   -0.5367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0362   -0.0098   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345    1.2539   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1846    0.9014   -0.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2699   -0.9062    0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7608   -2.1509    0.3866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -1.0213    1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425    0.1243    2.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5670    2.1923   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4112    0.6383    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4530    0.9470   -1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2261    1.2761   -3.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5184   -1.4946    2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596   -1.7980   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448   -0.4838   -1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5846    1.7366    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7437    1.9820   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3115   -0.0813   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058   -0.4359    1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3496   -2.3463   -0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840   -1.9533    1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    0.6469    1.7069 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 19 12  1  0
 11  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(Hydroxymethyl)-5-[6-(methylsulphanyl)-9H-purin-9-yl]oxolane-3,4-diol	Generator
6-Methylthiopurine riboside	MeSH
Riboside, 6-methylmercaptopurine	MeSH
6 Methylthiopurine riboside	MeSH
Methylthioinosine	MeSH
Riboside, 6-methylthiopurine	MeSH
6 Methylmercaptopurine riboside	MeSH
6-Methylmercaptopurine riboside	MeSH

Chemical Formula

C₁₁H₁₄N₄O₄S

Average Molecular Weight

298.32

Monoisotopic Molecular Weight

298.073576121

IUPAC Name

2-(hydroxymethyl)-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolane-3,4-diol

Traditional Name

6-methyl mp riboside

CAS Registry Number

Not Available

SMILES

CSC1=NC=NC2=C1N=CN2C1OC(CO)C(O)C1O

InChI Identifier

InChI=1S/C11H14N4O4S/c1-20-10-6-9(12-3-13-10)15(4-14-6)11-8(18)7(17)5(2-16)19-11/h3-5,7-8,11,16-18H,2H2,1H3

InChI Key

ZDRFDHHANOYUTE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
6-thiopurine
Imidazopyrimidine
Purine
Aryl thioether
Alkylarylthioether
Monosaccharide
N-substituted imidazole
Pyrimidine
Imidazole
Tetrahydrofuran
Azole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Sulfenyl compound
Thioether
Oxacycle
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	-0.4	ALOGPS
logP	-0.63	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	2.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.25 m³·mol⁻¹	ChemAxon
Polarizability	28.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	165.149	30932474
DeepCCS	[M-H]-	162.791	30932474
DeepCCS	[M-2H]-	195.677	30932474
DeepCCS	[M+Na]+	171.242	30932474
AllCCS	[M+H]+	167.7	32859911
AllCCS	[M+H-H2O]+	164.4	32859911
AllCCS	[M+NH4]+	170.7	32859911
AllCCS	[M+Na]+	171.6	32859911
AllCCS	[M-H]-	165.1	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	164.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.9437 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1890.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	95.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	155.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	322.1 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	320.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	672.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	288.1 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	975.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	402.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	284.9 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	102.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Methylthioinosine	CSC1=NC=NC2=C1N=CN2C1OC(CO)C(O)C1O	3537.4	Standard polar	33892256
6-Methylthioinosine	CSC1=NC=NC2=C1N=CN2C1OC(CO)C(O)C1O	2505.4	Standard non polar	33892256
6-Methylthioinosine	CSC1=NC=NC2=C1N=CN2C1OC(CO)C(O)C1O	2808.5	Semi standard non polar	33892256

Spectra

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

237358

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 6-Methylthioinosine (HMDB0242752)

MOL for HMDB0242752 (6-Methylthioinosine)

3D MOL for HMDB0242752 (6-Methylthioinosine)

3D SDF for HMDB0242752 (6-Methylthioinosine)

3D-SDF for HMDB0242752 (6-Methylthioinosine)

PDB for HMDB0242752 (6-Methylthioinosine)

3D PDB for HMDB0242752 (6-Methylthioinosine)

SMILES for HMDB0242752 (6-Methylthioinosine)

INCHI for HMDB0242752 (6-Methylthioinosine)

Structure for HMDB0242752 (6-Methylthioinosine)

3D Structure for HMDB0242752 (6-Methylthioinosine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized