MiMeDB: Showing metabocard for 5'-S-methyl-5'-thioadenosine (MMDBc0047847)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:45:45 UTC

Update Date

2024-04-30 20:31:48 UTC

Metabolite ID

MMDBc0047847

Metabolite Identification

Common Name

5'-S-methyl-5'-thioadenosine

Description

5'-S-methyl-5'-thioadenosine belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. 5'-S-methyl-5'-thioadenosine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 5'-S-methyl-5'-thioadenosine.

Structure

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

HMDB0257557
     RDKit          3D
(2R,5S)-2-(6-Aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.3419    0.0152   -1.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004    0.4760    0.0878 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.9672   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9570   -0.1281   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6568    0.3770   -0.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822   -0.0252    0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071    0.2107    0.7895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511    0.2895    1.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2466    0.5175    1.8066 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4749    0.5919    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6402    0.8123   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8706    1.0060    0.4625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5117    0.8267   -1.5542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3328    0.6400   -2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    0.4271   -1.4475 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    0.4005   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4420   -1.5186    0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1002   -2.0204   -0.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9544   -1.3174    0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645   -1.0751    1.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8926   -0.9476   -1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3020    0.8145   -2.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4191   -0.2120   -1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859    1.3928    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    1.8150   -0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2624   -0.4770   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6950    0.3963    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4952    0.1844    2.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2739    0.2302    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3423    1.9227    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    0.6640   -3.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -2.0380    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5168   -1.8015   -1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4147   -2.2193   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8081   -1.1973    2.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  4  1  0
 16  7  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

Structure #1
  Mrv0541 02241206112D          

 20 22  0  0  0  0            999 V2000
   -1.1495    5.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683    4.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    4.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    4.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687    3.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    5.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937    3.6424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    3.2299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820    5.3603    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2  5  1  0  0  0  0
  2 20  1  0  0  0  0
  3 13  2  0  0  0  0
  3 14  1  0  0  0  0
  4 15  2  0  0  0  0
  4 16  1  0  0  0  0
  5  7  1  0  0  0  0
  5 19  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  7 17  1  0  0  0  0
  8 11  1  0  0  0  0
  8 18  1  0  0  0  0
  9 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  2  0  0  0  0
 10 16  1  0  0  0  0
 11 16  1  0  0  0  0
 11 19  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047847

> <DATABASE_NAME>
MIME

> <SMILES>
CSCC1OC(C(O)C1O)N1C=NC2=C(N)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)

> <INCHI_KEY>
WUUGFSXJNOTRMR-UHFFFAOYSA-N

> <FORMULA>
C11H15N5O3S

> <MOLECULAR_WEIGHT>
297.334

> <EXACT_MASS>
297.089560061

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
29.75242425067167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-0.6084927256666669

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.012986053756393

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.471831351439768

> <JCHEM_PKA_STRONGEST_BASIC>
4.98844821709019

> <JCHEM_POLAR_SURFACE_AREA>
119.31000000000002

> <JCHEM_REFRACTIVITY>
74.0292

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(6-aminopurin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257557
     RDKit          3D
(2R,5S)-2-(6-Aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.3419    0.0152   -1.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004    0.4760    0.0878 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.9672   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9570   -0.1281   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6568    0.3770   -0.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822   -0.0252    0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071    0.2107    0.7895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511    0.2895    1.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2466    0.5175    1.8066 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4749    0.5919    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6402    0.8123   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8706    1.0060    0.4625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5117    0.8267   -1.5542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3328    0.6400   -2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    0.4271   -1.4475 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    0.4005   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4420   -1.5186    0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1002   -2.0204   -0.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9544   -1.3174    0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645   -1.0751    1.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8926   -0.9476   -1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3020    0.8145   -2.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4191   -0.2120   -1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859    1.3928    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    1.8150   -0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2624   -0.4770   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6950    0.3963    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4952    0.1844    2.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2739    0.2302    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3423    1.9227    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    0.6640   -3.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -2.0380    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5168   -1.8015   -1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4147   -2.2193   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8081   -1.1973    2.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  4  1  0
 16  7  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.146  10.911   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.061   8.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.185   7.569   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.650   8.045   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.555   6.799   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.924  -0.237   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       6.258   2.073   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       4.924   4.383   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       2.126   9.510   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.095   6.799   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.185   6.029   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0      -0.900  10.006   0.000  0.00  0.00           S+0
CONECT    1   20                                                            
CONECT    2    5   20                                                       
CONECT    3   13   14                                                       
CONECT    4   15   16                                                       
CONECT    5    2    7   19                                                  
CONECT    6    9   10   15                                                  
CONECT    7    5    8   17                                                  
CONECT    8    7   11   18                                                  
CONECT    9    6   12   13                                                  
CONECT   10    6   14   16                                                  
CONECT   11    8   16   19                                                  
CONECT   12    9                                                            
CONECT   13    3    9                                                       
CONECT   14    3   10                                                       
CONECT   15    4    6                                                       
CONECT   16    4   10   11                                                  
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    5   11                                                       
CONECT   20    1    2                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0257557
HETATM    1  C1  UNL     1       5.342   0.015  -1.481  1.00  0.00           C  
HETATM    2  S1  UNL     1       4.600   0.476   0.088  1.00  0.00           S  
HETATM    3  C2  UNL     1       2.894   0.967  -0.040  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.957  -0.128  -0.448  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.657   0.377  -0.511  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.082  -0.025   0.681  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.307   0.211   0.789  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.951   0.289   1.991  1.00  0.00           C  
HETATM    9  N2  UNL     1      -3.247   0.517   1.807  1.00  0.00           N  
HETATM   10  C6  UNL     1      -3.475   0.592   0.506  1.00  0.00           C  
HETATM   11  C7  UNL     1      -4.640   0.812  -0.205  1.00  0.00           C  
HETATM   12  N3  UNL     1      -5.871   1.006   0.462  1.00  0.00           N  
HETATM   13  N4  UNL     1      -4.512   0.827  -1.554  1.00  0.00           N  
HETATM   14  C8  UNL     1      -3.333   0.640  -2.168  1.00  0.00           C  
HETATM   15  N5  UNL     1      -2.212   0.427  -1.448  1.00  0.00           N  
HETATM   16  C9  UNL     1      -2.266   0.400  -0.124  1.00  0.00           C  
HETATM   17  C10 UNL     1       0.442  -1.519   0.635  1.00  0.00           C  
HETATM   18  O2  UNL     1      -0.100  -2.020  -0.516  1.00  0.00           O  
HETATM   19  C11 UNL     1       1.954  -1.317   0.445  1.00  0.00           C  
HETATM   20  O3  UNL     1       2.464  -1.075   1.710  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.893  -0.948  -1.859  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.302   0.814  -2.248  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.419  -0.212  -1.295  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.586   1.393   0.954  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.823   1.815  -0.748  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.262  -0.477  -1.471  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.695   0.396   1.498  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.495   0.184   2.972  1.00  0.00           H  
HETATM   29  H9  UNL     1      -6.274   0.230   1.010  1.00  0.00           H  
HETATM   30  H10 UNL     1      -6.342   1.923   0.389  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.292   0.664  -3.261  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.204  -2.038   1.552  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.517  -1.801  -1.267  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.415  -2.219  -0.031  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.808  -1.197   2.439  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4   24   25
CONECT    4    5   19   26
CONECT    5    6
CONECT    6    7   17   27
CONECT    7    8   16
CONECT    8    9    9   28
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12   13
CONECT   12   29   30
CONECT   13   14   14
CONECT   14   15   31
CONECT   15   16   16
CONECT   17   18   19   32
CONECT   18   33
CONECT   19   20   34
CONECT   20   35
END

HMDB0257557
     RDKit          3D
(2R,5S)-2-(6-Aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.3419    0.0152   -1.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004    0.4760    0.0878 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.9672   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9570   -0.1281   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6568    0.3770   -0.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822   -0.0252    0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071    0.2107    0.7895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511    0.2895    1.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2466    0.5175    1.8066 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4749    0.5919    0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6402    0.8123   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8706    1.0060    0.4625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5117    0.8267   -1.5542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3328    0.6400   -2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    0.4271   -1.4475 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    0.4005   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4420   -1.5186    0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1002   -2.0204   -0.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9544   -1.3174    0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645   -1.0751    1.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8926   -0.9476   -1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3020    0.8145   -2.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4191   -0.2120   -1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859    1.3928    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    1.8150   -0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2624   -0.4770   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6950    0.3963    1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4952    0.1844    2.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2739    0.2302    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3423    1.9227    0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    0.6640   -3.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -2.0380    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5168   -1.8015   -1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4147   -2.2193   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8081   -1.1973    2.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  4  1  0
 16  7  1  0
 16 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

Synonyms

Value	Source
xylo-MTA	MeSH
9-(5'-Deoxy-5'-(methylthio)-xylofuranosyl)adenine	MeSH
9-(5'Deoxy-5'-(methylthio)-beta-D-xylofuranosyl)adenine	MeSH
9-DMXA	MeSH
Xylosyl-methylthio-adenosine	MeSH

Molecular Formula

C₁₁H₁₅N₅O₃S

Average Mass

297.334

Monoisotopic Mass

297.089560061

IUPAC Name

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

Traditional Name

2-(6-aminopurin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol

CAS Registry Number

Not Available

SMILES

CSCC1OC(C(O)C1O)N1C=NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)

InChI Key

WUUGFSXJNOTRMR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

5'-deoxyribonucleosides

Sub Class

5'-deoxy-5'-thionucleosides

Direct Parent

5'-deoxy-5'-thionucleosides

Alternative Parents

Substituents

5'-deoxy-5'-thionucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monosaccharide
N-substituted imidazole
Pyrimidine
Imidolactam
Azole
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Dialkylthioether
Sulfenyl compound
Thioether
Azacycle
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Amine
Primary amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (5-METHYLTHIOADENOSINE )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.5 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	-0.61	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.31 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.03 m³·mol⁻¹	ChemAxon
Polarizability	29.75 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ta-6960000000-57c0c27b9d7ed3b52a50	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0910000000-5bf333f976c26a4c9b39	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0940000000-eb168427f389d7079abf	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-714e20a3376683008e65	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900000000-cb0adab85341c49ced5b	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9220000000-14da12fd68bc6d33eed9	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4910000000-324b5daf65bdaa0d2bdb	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-4900000000-14e9c89fcdd488f204aa	2016-09-14	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0257557

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

144

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

149

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 5'-S-methyl-5'-thioadenosine (MMDBc0047847)

MOL for #<Metabolite:0x00005634c29c7b18>

3D MOL for #<Metabolite:0x00005634c29c7b18>

3D SDF for #<Metabolite:0x00005634c29c7b18>

3D-SDF for #<Metabolite:0x00005634c29c7b18>

PDB for #<Metabolite:0x00005634c29c7b18>

3D PDB for #<Metabolite:0x00005634c29c7b18>

SMILES for #<Metabolite:0x00005634c29c7b18>

INCHI for #<Metabolite:0x00005634c29c7b18>

Structure for #<Metabolite:0x00005634c29c7b18>

3D Structure for #<Metabolite:0x00005634c29c7b18>