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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:45:41 UTC

HMDB ID

HMDB0001173

Secondary Accession Numbers

HMDB01173

Metabolite Identification

Common Name

5'-Methylthioadenosine

Description

5'-Methylthioadenosine, also known as MTA or thiomethyladenosine, 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'-Methylthioadenosine is metabolized solely by MTA-phosphorylase, to yield 5-methylthioribose-1-phosphate and adenine, a crucial step in the methionine and purine salvage pathways, respectively. 5'-Methylthioadenosine exists in all living species, ranging from bacteria to humans. 5'-Methylthioadenosine (MTA) is a naturally occurring sulfur-containing nucleoside present in all mammalian tissues. Within humans, 5'-methylthioadenosine participates in a number of enzymatic reactions. In particular, 5'-methylthioadenosine and spermidine can be biosynthesized from S-adenosylmethioninamine and putrescine through the action of the enzyme spermidine synthase. In addition, 5'-methylthioadenosine can be converted into 5-methylthioribose 1-phosphate and L-methionine; which is catalyzed by the enzyme S-methyl-5'-thioadenosine phosphorylase. It is produced from S-adenosylmethionine mainly through the polyamine biosynthetic pathway, where it behaves as a powerful inhibitory product. For instance, 5'-Methylthioadenosine has been shown to influence the regulation of gene expression, proliferation, differentiation, and apoptosis (PMID:15313459 ). In humans, 5'-methylthioadenosine is involved in the metabolic disorder called hypermethioninemia. Outside of the human body, 5'-Methylthioadenosine has been detected, but not quantified in several different foods, such as soursops, allspices, summer grapes, alaska wild rhubarbs, and breadfruits. Elevated excretion appears in children with severe combined immunodeficiency syndrome (SCID) (PMID:3987052 ). Evidence suggests that 5'-Methylthioadenosine can affect cellular processes in many ways. 5'-Methylthioadenosine can be found in human urine.

Structure

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

HMDB0001173
     RDKit          3D
5'-Methylthioadenosine
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.4626    1.1326    1.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701   -0.6001    0.9338 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655   -1.3757    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0637   -0.9271   -0.3377 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8087   -1.5720   -0.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -0.8829   -1.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3744   -0.9365   -0.9378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2684   -1.8240   -1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937   -1.5767   -0.8970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3660   -0.4975   -0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444    0.2267    0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6099   -0.1528    0.7280 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7931    1.2822    1.3750 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5081    1.6274    1.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    0.9388    0.5712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495   -0.1107   -0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5674    0.4833   -1.4099 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2012    0.5978   -2.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6904    0.5135   -0.3964 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7396    1.3169   -0.8641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9580    1.7565    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443    1.3005    2.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5009    1.5396    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0524   -2.4881    0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -1.2830    1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -1.1499   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1419   -1.4348   -2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0760   -2.6490   -2.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3164    0.3126    0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9060   -0.9045    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943    2.5005    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600    1.2984   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    0.4632   -3.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3477    0.8291    0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5092    2.2458   -0.5511 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  6
  6 27  1  6
  8 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 17 32  1  1
 18 33  1  0
 19 34  1  1
 20 35  1  0
M  END

  Mrv1652309042000182D          

 20 22  0  0  0  0            999 V2000
 9999.8190 9998.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.6078 9998.0639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1173 9999.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8310 9999.5108    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10003.5467 9999.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.731610000.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3191 9998.7355    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.1441 9998.7355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.3990 9999.5201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.606710000.3270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2187 9999.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0472 9998.9672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6604 9998.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4449 9998.6700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6167 9999.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.003710000.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3313 9999.8898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.159810000.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.339410000.7830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.0849 9999.5541    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6  9  1  0  0  0  0
  8  2  1  1  0  0  0
  9  3  1  6  0  0  0
  7  1  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 11 10  1  0  0  0  0
 15 16  2  0  0  0  0
 14 15  1  0  0  0  0
 16 11  1  0  0  0  0
 18 19  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 15 17  1  0  0  0  0
 20 17  1  6  0  0  0
  6 20  1  0  0  0  0
 20  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001173

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N

> <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)/t5-,7-,8-,11-/m1/s1

> <INCHI_KEY>
WUUGFSXJNOTRMR-IOSLPCCCSA-N

> <FORMULA>
C11H15N5O3S

> <MOLECULAR_WEIGHT>
297.334

> <EXACT_MASS>
297.089560061

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.256574959298177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S)-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>
14.012986053228548

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.47183133876813

> <JCHEM_PKA_STRONGEST_BASIC>
3.9212883219836336

> <JCHEM_POLAR_SURFACE_AREA>
119.31

> <JCHEM_REFRACTIVITY>
74.02919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylthioadenosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001173
     RDKit          3D
5'-Methylthioadenosine
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.4626    1.1326    1.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701   -0.6001    0.9338 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655   -1.3757    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0637   -0.9271   -0.3377 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8087   -1.5720   -0.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -0.8829   -1.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3744   -0.9365   -0.9378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2684   -1.8240   -1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937   -1.5767   -0.8970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3660   -0.4975   -0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444    0.2267    0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6099   -0.1528    0.7280 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7931    1.2822    1.3750 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5081    1.6274    1.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    0.9388    0.5712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495   -0.1107   -0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5674    0.4833   -1.4099 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2012    0.5978   -2.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6904    0.5135   -0.3964 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7396    1.3169   -0.8641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9580    1.7565    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443    1.3005    2.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5009    1.5396    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0524   -2.4881    0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -1.2830    1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -1.1499   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1419   -1.4348   -2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0760   -2.6490   -2.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3164    0.3126    0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9060   -0.9045    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943    2.5005    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600    1.2984   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    0.4632   -3.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3477    0.8291    0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5092    2.2458   -0.5511 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  6
  6 27  1  6
  8 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 17 32  1  1
 18 33  1  0
 19 34  1  1
 20 35  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.3298663.068   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8669.6688663.053   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8670.6198666.525   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0    8671.9518665.753   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0    8673.2878666.525   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8668.0328666.676   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8667.2628664.306   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.8028664.306   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.2788665.771   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0    8660.3338667.277   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8661.4758666.245   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8661.1558664.739   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8662.2998663.708   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8663.7648664.184   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8664.0858665.691   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.9408666.722   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    8665.4188666.461   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0    8665.0988667.967   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0    8663.5678668.128   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0    8666.8258665.834   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    4    9                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    9   20                                                       
CONECT    7    8    1   20                                                  
CONECT    8    7    9    2                                                  
CONECT    9    8    6    3                                                  
CONECT   10   11                                                            
CONECT   11   12   10   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   16   14   17                                                  
CONECT   16   15   11   19                                                  
CONECT   17   18   15   20                                                  
CONECT   18   19   17                                                       
CONECT   19   18   16                                                       
CONECT   20   17    6    7                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0001173
HETATM    1  C1  UNL     1       4.463   1.133   1.383  1.00  0.00           C  
HETATM    2  S1  UNL     1       4.470  -0.600   0.934  1.00  0.00           S  
HETATM    3  C2  UNL     1       2.865  -1.376   0.828  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.064  -0.927  -0.338  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.809  -1.572  -0.359  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.028  -0.883  -1.250  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.374  -0.936  -0.938  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.268  -1.824  -1.395  1.00  0.00           C  
HETATM    9  N2  UNL     1      -3.494  -1.577  -0.897  1.00  0.00           N  
HETATM   10  C6  UNL     1      -3.366  -0.497  -0.100  1.00  0.00           C  
HETATM   11  C7  UNL     1      -4.244   0.227   0.677  1.00  0.00           C  
HETATM   12  N3  UNL     1      -5.610  -0.153   0.728  1.00  0.00           N  
HETATM   13  N4  UNL     1      -3.793   1.282   1.375  1.00  0.00           N  
HETATM   14  C8  UNL     1      -2.508   1.627   1.317  1.00  0.00           C  
HETATM   15  N5  UNL     1      -1.645   0.939   0.571  1.00  0.00           N  
HETATM   16  C9  UNL     1      -2.049  -0.111  -0.134  1.00  0.00           C  
HETATM   17  C10 UNL     1       0.567   0.483  -1.410  1.00  0.00           C  
HETATM   18  O2  UNL     1       1.201   0.598  -2.667  1.00  0.00           O  
HETATM   19  C11 UNL     1       1.690   0.514  -0.396  1.00  0.00           C  
HETATM   20  O3  UNL     1       2.740   1.317  -0.864  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.958   1.756   0.592  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.144   1.301   2.283  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.501   1.540   1.706  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.052  -2.488   0.730  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.311  -1.283   1.794  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.592  -1.150  -1.313  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.142  -1.435  -2.234  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.076  -2.649  -2.077  1.00  0.00           H  
HETATM   29  H9  UNL     1      -6.316   0.313   0.113  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.906  -0.905   1.388  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.194   2.501   1.910  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.160   1.298  -1.259  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.551   0.463  -3.399  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.348   0.829   0.612  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.509   2.246  -0.551  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

HMDB0001173
     RDKit          3D
5'-Methylthioadenosine
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.4626    1.1326    1.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701   -0.6001    0.9338 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655   -1.3757    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0637   -0.9271   -0.3377 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8087   -1.5720   -0.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -0.8829   -1.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3744   -0.9365   -0.9378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2684   -1.8240   -1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937   -1.5767   -0.8970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3660   -0.4975   -0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444    0.2267    0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6099   -0.1528    0.7280 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7931    1.2822    1.3750 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5081    1.6274    1.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    0.9388    0.5712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0495   -0.1107   -0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5674    0.4833   -1.4099 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2012    0.5978   -2.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6904    0.5135   -0.3964 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7396    1.3169   -0.8641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9580    1.7565    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443    1.3005    2.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5009    1.5396    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0524   -2.4881    0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -1.2830    1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -1.1499   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1419   -1.4348   -2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0760   -2.6490   -2.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3164    0.3126    0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9060   -0.9045    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943    2.5005    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600    1.2984   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    0.4632   -3.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3477    0.8291    0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5092    2.2458   -0.5511 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  6
  6 27  1  6
  8 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 17 32  1  1
 18 33  1  0
 19 34  1  1
 20 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5'-Deoxy-5'-(methylthio)adenosine	ChEBI
5-Methylthioadenosine	ChEBI
9-(5-S-Methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine	ChEBI
Methylthioadenosine	ChEBI
MTA	ChEBI
S-Methyl-5'-thioadenosine	ChEBI
Thiomethyladenosine	ChEBI
9-(5-S-Methyl-5-thio-b-D-ribofuranosyl)-9H-purin-6-amine	Generator
9-(5-S-Methyl-5-thio-β-D-ribofuranosyl)-9H-purin-6-amine	Generator
1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-ribofuranose	HMDB
1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-ribofuranose	HMDB
5'-(Methylthio)-5'-deoxyadenosine	HMDB
5'-(Methylthio)adenosine	HMDB
5'-S-Methyl-5'-thio-adenosine	HMDB
5'-S-Methyl-5'-thioadenosine	HMDB
S-Methyl-5-thioadenosine	HMDB
Adenine(5'-deoxy-5'-methylthio)9-beta-D-furanoriboside	HMDB
5-MTDA	HMDB
5'-Methylthio-5'-deoxyadenosine	HMDB
5'-Deoxy-5'-methylthioadenosine	HMDB
5'-Methylthioadenosine, methyl-(14)C-labeled	HMDB
5'-Methylthioadenosine	ChEBI

Chemical Formula

C₁₁H₁₅N₅O₃S

Average Molecular Weight

297.334

Monoisotopic Molecular Weight

297.089560061

IUPAC Name

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

Traditional Name

methylthioadenosine

CAS Registry Number

2457-80-9

SMILES

CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N

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)/t5-,7-,8-,11-/m1/s1

InChI Key

WUUGFSXJNOTRMR-IOSLPCCCSA-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

thioadenosine (CHEBI:17509 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001173)

Cell

Fibroblasts (HMDB: HMDB0001173)

Hematocyte

Platelet (HMDB: HMDB0001173)

Organ

Prostate (HMDB: HMDB0001173)
Placenta (HMDB: HMDB0001173)

Excreta

Biofluid or Excreta

Urine (PMID: 9129323)
Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0001173)

Source

Exogenous

Exogenous (HMDB: HMDB0001173)

Food

Animal origin

Poultry

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)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0001173)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Methylenetetrahydrofolate Reductase Deficiency (MTHFRD) (PathBank: SMP0000340)
Cystathionine beta-Synthase Deficiency (PathBank: SMP0120471)
Hypermethioninemia (PathBank: SMP0120498)
Glycine N-Methyltransferase Deficiency (PathBank: SMP0120707)
Methionine Adenosyltransferase Deficiency (PathBank: SMP0120739)
Homocystinuria-Megaloblastic Anemia Due to Defect in Cobalamin Metabolism, cblG Complementation Type (PathBank: SMP0120853)
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency (PathBank: SMP0120747)

Metabolic pathway

Methionine Metabolism (PathBank: SMP0063637)
Spermidine and Spermine Biosynthesis (PathBank: SMP0063671)
Spermidine Biosynthesis I (PathBank: SMP0122229)
Beta-Alanine metabolism (PathBank: SMP0002307)
Aminopropylcadaverine Biosynthesis (PathBank: SMP0122228)

Role

Not Available

Physical Properties

State

Solid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	170.344	30932474
[M+H]+	Baker	173.025	30932474
[M-H]-	Not Available	168.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000159
[M+H]+	Not Available	167.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000159

Predicted Molecular 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)	3.92	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	29.26 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
DarkChem	[M+H]+	170.206	31661259
DarkChem	[M-H]-	164.816	31661259
AllCCS	[M+H]+	167.317	32859911
AllCCS	[M-H]-	165.602	32859911
DeepCCS	[M+H]+	158.492	30932474
DeepCCS	[M-H]-	156.097	30932474
DeepCCS	[M-2H]-	190.395	30932474
DeepCCS	[M+Na]+	165.064	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	164.1	32859911
AllCCS	[M+NH4]+	170.3	32859911
AllCCS	[M+Na]+	171.1	32859911
AllCCS	[M-H]-	165.6	32859911
AllCCS	[M+Na-2H]-	165.3	32859911
AllCCS	[M+HCOO]-	165.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5'-Methylthioadenosine	CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N	3690.3	Standard polar	33892256
5'-Methylthioadenosine	CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N	2644.9	Standard non polar	33892256
5'-Methylthioadenosine	CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N	2798.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5'-Methylthioadenosine,1TMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2746.4	Semi standard non polar	33892256
5'-Methylthioadenosine,1TMS,isomer #2	CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2744.3	Semi standard non polar	33892256
5'-Methylthioadenosine,1TMS,isomer #3	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O	2775.8	Semi standard non polar	33892256
5'-Methylthioadenosine,2TMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2689.2	Semi standard non polar	33892256
5'-Methylthioadenosine,2TMS,isomer #2	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2743.4	Semi standard non polar	33892256
5'-Methylthioadenosine,2TMS,isomer #3	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2738.7	Semi standard non polar	33892256
5'-Methylthioadenosine,2TMS,isomer #4	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O	2733.3	Semi standard non polar	33892256
5'-Methylthioadenosine,3TMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2739.7	Semi standard non polar	33892256
5'-Methylthioadenosine,3TMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2769.4	Standard non polar	33892256
5'-Methylthioadenosine,3TMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3998.1	Standard polar	33892256
5'-Methylthioadenosine,3TMS,isomer #2	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2744.4	Semi standard non polar	33892256
5'-Methylthioadenosine,3TMS,isomer #2	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2825.2	Standard non polar	33892256
5'-Methylthioadenosine,3TMS,isomer #2	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	3755.0	Standard polar	33892256
5'-Methylthioadenosine,3TMS,isomer #3	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2733.0	Semi standard non polar	33892256
5'-Methylthioadenosine,3TMS,isomer #3	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2817.3	Standard non polar	33892256
5'-Methylthioadenosine,3TMS,isomer #3	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	3702.1	Standard polar	33892256
5'-Methylthioadenosine,4TMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2759.5	Semi standard non polar	33892256
5'-Methylthioadenosine,4TMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2839.7	Standard non polar	33892256
5'-Methylthioadenosine,4TMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3414.5	Standard polar	33892256
5'-Methylthioadenosine,1TBDMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2964.2	Semi standard non polar	33892256
5'-Methylthioadenosine,1TBDMS,isomer #2	CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2959.6	Semi standard non polar	33892256
5'-Methylthioadenosine,1TBDMS,isomer #3	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O	2958.8	Semi standard non polar	33892256
5'-Methylthioadenosine,2TBDMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3099.4	Semi standard non polar	33892256
5'-Methylthioadenosine,2TBDMS,isomer #2	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3098.7	Semi standard non polar	33892256
5'-Methylthioadenosine,2TBDMS,isomer #3	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3088.3	Semi standard non polar	33892256
5'-Methylthioadenosine,2TBDMS,isomer #4	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O	3120.6	Semi standard non polar	33892256
5'-Methylthioadenosine,3TBDMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3298.2	Semi standard non polar	33892256
5'-Methylthioadenosine,3TBDMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3388.9	Standard non polar	33892256
5'-Methylthioadenosine,3TBDMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	4073.9	Standard polar	33892256
5'-Methylthioadenosine,3TBDMS,isomer #2	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3265.8	Semi standard non polar	33892256
5'-Methylthioadenosine,3TBDMS,isomer #2	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3445.2	Standard non polar	33892256
5'-Methylthioadenosine,3TBDMS,isomer #2	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3846.1	Standard polar	33892256
5'-Methylthioadenosine,3TBDMS,isomer #3	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3254.8	Semi standard non polar	33892256
5'-Methylthioadenosine,3TBDMS,isomer #3	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3441.8	Standard non polar	33892256
5'-Methylthioadenosine,3TBDMS,isomer #3	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3805.5	Standard polar	33892256
5'-Methylthioadenosine,4TBDMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3460.7	Semi standard non polar	33892256
5'-Methylthioadenosine,4TBDMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3592.9	Standard non polar	33892256
5'-Methylthioadenosine,4TBDMS,isomer #1	CSC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3688.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5'-Methylthioadenosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-0940000000-16b1106966ac98c7a107	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5'-Methylthioadenosine GC-EI-TOF (Non-derivatized)	splash10-000i-0940000000-16b1106966ac98c7a107	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5'-Methylthioadenosine GC-EI-TOF (Non-derivatized)	splash10-000i-0940000000-30fc68e7b5ff7576069b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5'-Methylthioadenosine GC-EI-TOF (Non-derivatized)	splash10-01ti-0900000000-312bd8eec3c461e919f9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Methylthioadenosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9530000000-5fbf6b1a856ad3827980	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Methylthioadenosine GC-MS (2 TMS) - 70eV, Positive	splash10-0h70-9636300000-67e425eba97fe420c464	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Methylthioadenosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Methylthioadenosine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000j-0940000000-55655e7a0a6c8acba0f0	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-1900000000-f37865ca2029a623ace7	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000i-2900000000-ae0e3df9bf25c100940d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0002-0090000000-72139812c5b2ede077ed	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-000i-0910000000-0c3d173f36272e3271eb	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-000i-0900000000-f3443ca133811f52c5d7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-000i-1900000000-49cc299525d7fca27818	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-000i-3900000000-39bebdcaa7ce2695465b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-000i-0900000000-76b935f4f0a78c15ca0e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0002-4900000000-d8c0df43305b934d71dc	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-000i-0900000000-d3bfbeb6fb95e3768ef6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-001i-0910000000-56784be58ef9065f21f6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QTOF , negative-QTOF	splash10-001i-0910000000-56784be58ef9065f21f6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ , positive-QTOF	splash10-0002-0090000000-72139812c5b2ede077ed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ , positive-QTOF	splash10-000i-0910000000-0c3d173f36272e3271eb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ , positive-QTOF	splash10-000i-0900000000-f3443ca133811f52c5d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ , positive-QTOF	splash10-000i-1900000000-6ec86a11bf8ad7331bd2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-QQ , positive-QTOF	splash10-000i-3900000000-39bebdcaa7ce2695465b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5'-Methylthioadenosine LC-ESI-IT , positive-QTOF	splash10-000i-0900000000-b9006ef8eecdaefc89a6	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methylthioadenosine 10V, Positive-QTOF	splash10-000i-0940000000-eb168427f389d7079abf	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methylthioadenosine 20V, Positive-QTOF	splash10-000i-0900000000-714e20a3376683008e65	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methylthioadenosine 40V, Positive-QTOF	splash10-000i-2900000000-cb0adab85341c49ced5b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methylthioadenosine 10V, Negative-QTOF	splash10-0002-9220000000-14da12fd68bc6d33eed9	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methylthioadenosine 20V, Negative-QTOF	splash10-001i-4910000000-324b5daf65bdaa0d2bdb	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Methylthioadenosine 40V, Negative-QTOF	splash10-053r-4900000000-14e9c89fcdd488f204aa	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Fibroblasts
Placenta
Platelet
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Methionine Metabolism
Spermidine and Spermine Biosynthesis		Not Available
Cystathionine Beta-Synthase Deficiency		Not Available
Hypermethioninemia		Not Available
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.12 +/- 0.05 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	9129323	details
Urine	Detected and Quantified	0.12 +/- 0.08 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9129323	details
Urine	Detected and Quantified	0.13 +/- 0.11 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9129323	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB02282

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031156

KNApSAcK ID

Not Available

Chemspider ID

388321

KEGG Compound ID

C00170

BioCyc ID

5-METHYLTHIOADENOSINE

BiGG ID

34127

Wikipedia Link

Not Available

METLIN ID

3425

PubChem Compound

439176

PDB ID

Not Available

ChEBI ID

17509

Food Biomarker Ontology

Not Available

VMH ID

5MTA

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Sufrin, Janice R.; Spiess, Arthur J.; Kramer, Debora L.; Libby, Paul R.; Porter, Carl W. Synthesis and antiproliferative effects of novel 5'-fluorinated analogs of 5'-deoxy-5'-(methylthio)adenosine. Journal of Medicinal Chemistry (1989), 32(5), 997-1001.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed:9129323 ]
Avila MA, Garcia-Trevijano ER, Lu SC, Corrales FJ, Mato JM: Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30. [PubMed:15313459 ]
Gerasimovskaya EV, Ahmad S, White CW, Jones PL, Carpenter TC, Stenmark KR: Extracellular ATP is an autocrine/paracrine regulator of hypoxia-induced adventitial fibroblast growth. Signaling through extracellular signal-regulated kinase-1/2 and the Egr-1 transcription factor. J Biol Chem. 2002 Nov 22;277(47):44638-50. Epub 2002 Sep 18. [PubMed:12244041 ]
Mills GC, Mills JS: Urinary excretion of methylthioadenosine in immunodeficient children. Clin Chim Acta. 1985 Mar 30;147(1):15-23. [PubMed:3987052 ]
Contreres JO, Dupuy E, Job B, Habib A, Bryckaert M, Rosa JP, Simoneau G, Herbert JM, Savi P, Levy-Toledano S: Effect of clopidogrel administration to healthy volunteers on platelet phosphorylation events triggered by ADP. Br J Haematol. 2003 Feb;120(4):633-42. [PubMed:12588350 ]
Mills GC, Schmalstieg FC, Goldblum RM: Urinary excretion of modified purines and nucleosides in immunodeficient children. Biochem Med. 1985 Aug;34(1):37-51. [PubMed:4052062 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. Spermine synthase

General function:: Involved in spermine synthase activity
Specific function:: Catalyzes the production of spermine from spermidine and decarboxylated S-adenosylmethionine (dcSAM).
Gene Name:: SMS
Uniprot ID:: P52788
Molecular weight:: 35278.2

Reactions

S-Adenosylmethioninamine + Spermidine → 5'-Methylthioadenosine + Spermine	details

Enzyme Details

2. Spermidine synthase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM). Has a strong preference for putrescine as substrate, and has very low activity towards 1,3-diaminopropane. Has extremely low activity towards spermidine.
Gene Name:: SRM
Uniprot ID:: P19623
Molecular weight:: 33824.455

Reactions

S-Adenosylmethioninamine + Putrescine → 5'-Methylthioadenosine + Spermidine	details
S-Adenosylmethioninamine + Spermidine → 5'-Methylthioadenosine + Spermine	details
S-Adenosylmethioninamine + Cadaverine → 5'-Methylthioadenosine + Aminopropylcadaverine	details

Enzyme Details

3. S-methyl-5'-thioadenosine phosphorylase

General function:: Involved in transferase activity, transferring pentosyl groups
Specific function:: Catalyzes the reversible phosphorylation of S-methyl-5'-thioadenosine (MTA) to adenine and 5-methylthioribose-1-phosphate. Involved in the breakdown of MTA, a major by-product of polyamine biosynthesis. Responsible for the first step in the methionine salvage pathway after MTA has been generated from S-adenosylmethionine. Has broad substrate specificity with 6-aminopurine nucleosides as preferred substrates.
Gene Name:: MTAP
Uniprot ID:: Q13126
Molecular weight:: 31235.76

Reactions

5'-Methylthioadenosine + Phosphate → Adenine + 5-Methylthioribose 1-phosphate	details

Showing metabocard for 5'-Methylthioadenosine (HMDB0001173)

MOL for HMDB0001173 (5'-Methylthioadenosine)

3D MOL for HMDB0001173 (5'-Methylthioadenosine)

3D SDF for HMDB0001173 (5'-Methylthioadenosine)

3D-SDF for HMDB0001173 (5'-Methylthioadenosine)

PDB for HMDB0001173 (5'-Methylthioadenosine)

3D PDB for HMDB0001173 (5'-Methylthioadenosine)

SMILES for HMDB0001173 (5'-Methylthioadenosine)

INCHI for HMDB0001173 (5'-Methylthioadenosine)

Structure for HMDB0001173 (5'-Methylthioadenosine)

3D Structure for HMDB0001173 (5'-Methylthioadenosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions