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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:00:57 UTC

Update Date

2021-09-14 14:58:17 UTC

HMDB ID

HMDB0060414

Secondary Accession Numbers

HMDB0061268
HMDB0061339
HMDB60414
HMDB61268
HMDB61339

Metabolite Identification

Common Name

6-Methylthiopurine 5'-monophosphate ribonucleotide

Description

6-Methylthiopurine 5'-monophosphate ribonucleotide, also known as methylthioinosine-5'-monophosphate or meTIMP, is a metabolite of mercaptopurine. Mercaptopurine (also called 6-mercaptopurine, 6-MP, or its brand name Purinethol) is an immunosuppressive drug. Mercaptopurine is in the thiopurine and antimetabolite family of medications (Wikipedia). MeTIMP produced from 6-thioinosine monophosphate (6-TIMP) by thiopurine methyltransferase (TPMT) is an active metabolite that can inhibit de novo purine biosynthesis. High concentration of meTIMP has been related to hepatotoxicity and myelotoxicity (PMID: 21311411 ).

Structure

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

HMDB0060414
     RDKit          3D
6-Methylthiopurine 5'-monophosphate ribonucleotide
 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.4410    2.5914    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0590    1.0104   -0.3550 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526   -0.2234   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9995   -1.4731   -0.8057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891   -2.3870   -0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603   -2.0290   -0.4221 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627   -0.7976    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958    0.1325    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0212    1.3056    0.4640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078    1.1335    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3884   -0.1368    0.4485 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0803   -0.7154    0.6003 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9427    0.2498    0.4701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0705   -0.5576    0.5064 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3498    0.2113    0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    0.8868   -0.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9383    1.6911   -0.8795 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.0474    0.6679   -0.6499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0230    2.8326    0.3719 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1591    2.5206   -2.3344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036   -1.5535   -0.5695 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3421   -2.7834   -0.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2751   -1.6719   -0.5125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1228   -2.9684   -0.2440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5688    2.9550   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0792    2.5153    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2214    3.3486    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2093   -3.3833   -1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700    1.9240    1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -1.1688    1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -1.0815    1.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070    0.9536    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807   -0.5216    0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1996    2.4043    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1563    2.5589   -2.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -1.2740   -1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9193   -2.6899    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -1.3215   -1.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0903   -3.1556    0.7074 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
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
 14 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  8  3  1  0
 23 12  1  0
 11  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
 10 29  1  0
 12 30  1  1
 14 31  1  1
 15 32  1  0
 15 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  6
 22 37  1  0
 23 38  1  6
 24 39  1  0
M  END

      
  Mrv1652307171819222D          

 24 26  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    3.1993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5644    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  2  0  0  0  0  0  0  0  0  0
    0.7403    2.1195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5644    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  2  0  0  0  0  0  0  0  0  0
    3.2789    1.2374    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
    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
    3.0966    5.7248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264    4.6853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0571    5.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868    4.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097    2.5320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417    4.9402    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2374    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  1  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
 11 15  1  1  0  0  0
  7 16  1  6  0  0  0
  8 17  1  6  0  0  0
 21  2  1  0  0  0  0
 22  5  1  0  0  0  0
 22 11  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
 23 20  2  0  0  0  0
 23 21  1  0  0  0  0
 24  1  1  0  0  0  0
 24 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060414

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N4O7PS/c1-24-10-6-9(12-3-13-10)15(4-14-6)11-8(17)7(16)5(22-11)2-21-23(18,19)20/h3-5,7-8,11,16-17H,2H2,1H3,(H2,18,19,20)/t5-,7-,8-,11-/m1/s1

> <INCHI_KEY>
BMYFUCYXRGTQQL-IOSLPCCCSA-N

> <FORMULA>
C11H15N4O7PS

> <MOLECULAR_WEIGHT>
378.298

> <EXACT_MASS>
378.039906056

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.61019367020917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-2.03

> <JCHEM_LOGP>
-2.062104902772542

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.250573303285374

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.191109001207523

> <JCHEM_PKA_STRONGEST_BASIC>
2.3474417131841308

> <JCHEM_POLAR_SURFACE_AREA>
160.04999999999998

> <JCHEM_REFRACTIVITY>
82.12699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Me-TIMP

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060414
     RDKit          3D
6-Methylthiopurine 5'-monophosphate ribonucleotide
 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.4410    2.5914    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0590    1.0104   -0.3550 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526   -0.2234   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9995   -1.4731   -0.8057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891   -2.3870   -0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603   -2.0290   -0.4221 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627   -0.7976    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958    0.1325    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0212    1.3056    0.4640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078    1.1335    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3884   -0.1368    0.4485 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0803   -0.7154    0.6003 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9427    0.2498    0.4701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0705   -0.5576    0.5064 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3498    0.2113    0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    0.8868   -0.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9383    1.6911   -0.8795 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.0474    0.6679   -0.6499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0230    2.8326    0.3719 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1591    2.5206   -2.3344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036   -1.5535   -0.5695 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3421   -2.7834   -0.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2751   -1.6719   -0.5125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1228   -2.9684   -0.2440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5688    2.9550   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0792    2.5153    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2214    3.3486    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2093   -3.3833   -1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700    1.9240    1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -1.1688    1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -1.0815    1.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070    0.9536    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807   -0.5216    0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1996    2.4043    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1563    2.5589   -2.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -1.2740   -1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9193   -2.6899    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -1.3215   -1.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0903   -3.1556    0.7074 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
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
 14 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  8  3  1  0
 23 12  1  0
 11  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
 10 29  1  0
 12 30  1  1
 14 31  1  1
 15 32  1  0
 15 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  6
 22 37  1  0
 23 38  1  6
 24 39  1  0
M  END

HEADER    PROTEIN                                 17-JUL-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-18         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       0.136   6.402   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.136   3.051   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.780  10.686   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.769   8.746   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.840   9.698   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.829   7.757   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.751   4.726   0.000  0.00  0.00           O+0
HETATM   23  P   UNK     0       5.305   9.222   0.000  0.00  0.00           P+0
HETATM   24  S   UNK     0       6.121  -2.310   0.000  0.00  0.00           S+0
CONECT    1   24                                                            
CONECT    2    5   21                                                       
CONECT    3   12   13                                                       
CONECT    4   14   15                                                       
CONECT    5    2    7   22                                                  
CONECT    6    9   10   14                                                  
CONECT    7    5    8   16                                                  
CONECT    8    7   11   17                                                  
CONECT    9    6   12   15                                                  
CONECT   10    6   13   24                                                  
CONECT   11    8   15   22                                                  
CONECT   12    3    9                                                       
CONECT   13    3   10                                                       
CONECT   14    4    6                                                       
CONECT   15    4    9   11                                                  
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18   23                                                            
CONECT   19   23                                                            
CONECT   20   23                                                            
CONECT   21    2   23                                                       
CONECT   22    5   11                                                       
CONECT   23   18   19   20   21                                             
CONECT   24    1   10                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0060414
HETATM    1  C1  UNL     1      -5.441   2.591   0.244  1.00  0.00           C  
HETATM    2  S1  UNL     1      -6.059   1.010  -0.355  1.00  0.00           S  
HETATM    3  C2  UNL     1      -4.753  -0.223  -0.390  1.00  0.00           C  
HETATM    4  N1  UNL     1      -4.999  -1.473  -0.806  1.00  0.00           N  
HETATM    5  C3  UNL     1      -3.989  -2.387  -0.821  1.00  0.00           C  
HETATM    6  N2  UNL     1      -2.760  -2.029  -0.422  1.00  0.00           N  
HETATM    7  C4  UNL     1      -2.463  -0.798   0.000  1.00  0.00           C  
HETATM    8  C5  UNL     1      -3.496   0.132   0.015  1.00  0.00           C  
HETATM    9  N3  UNL     1      -3.021   1.306   0.464  1.00  0.00           N  
HETATM   10  C6  UNL     1      -1.708   1.133   0.733  1.00  0.00           C  
HETATM   11  N4  UNL     1      -1.388  -0.137   0.448  1.00  0.00           N  
HETATM   12  C7  UNL     1      -0.080  -0.715   0.600  1.00  0.00           C  
HETATM   13  O1  UNL     1       0.943   0.250   0.470  1.00  0.00           O  
HETATM   14  C8  UNL     1       2.070  -0.558   0.506  1.00  0.00           C  
HETATM   15  C9  UNL     1       3.350   0.211   0.328  1.00  0.00           C  
HETATM   16  O2  UNL     1       3.429   0.887  -0.862  1.00  0.00           O  
HETATM   17  P1  UNL     1       4.938   1.691  -0.880  1.00  0.00           P  
HETATM   18  O3  UNL     1       6.047   0.668  -0.650  1.00  0.00           O  
HETATM   19  O4  UNL     1       5.023   2.833   0.372  1.00  0.00           O  
HETATM   20  O5  UNL     1       5.159   2.521  -2.334  1.00  0.00           O  
HETATM   21  C10 UNL     1       1.804  -1.553  -0.569  1.00  0.00           C  
HETATM   22  O6  UNL     1       2.342  -2.783  -0.151  1.00  0.00           O  
HETATM   23  C11 UNL     1       0.275  -1.672  -0.513  1.00  0.00           C  
HETATM   24  O7  UNL     1      -0.123  -2.968  -0.244  1.00  0.00           O  
HETATM   25  H1  UNL     1      -4.569   2.955  -0.351  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.079   2.515   1.305  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.221   3.349   0.153  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.209  -3.383  -1.158  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.070   1.924   1.112  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.080  -1.169   1.609  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.069  -1.082   1.482  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.407   0.954   1.153  1.00  0.00           H  
HETATM   33  H9  UNL     1       4.181  -0.522   0.371  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.200   2.404   1.249  1.00  0.00           H  
HETATM   35  H11 UNL     1       6.156   2.559  -2.476  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.148  -1.274  -1.566  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.919  -2.690   0.639  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.202  -1.321  -1.429  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.090  -3.156   0.707  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5
CONECT    5    6    6   28
CONECT    6    7
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10   10
CONECT   10   11   29
CONECT   11   12
CONECT   12   13   23   30
CONECT   13   14
CONECT   14   15   21   31
CONECT   15   16   32   33
CONECT   16   17
CONECT   17   18   18   19   20
CONECT   19   34
CONECT   20   35
CONECT   21   22   23   36
CONECT   22   37
CONECT   23   24   38
CONECT   24   39
END

HMDB0060414
     RDKit          3D
6-Methylthiopurine 5'-monophosphate ribonucleotide
 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.4410    2.5914    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0590    1.0104   -0.3550 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526   -0.2234   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9995   -1.4731   -0.8057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891   -2.3870   -0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603   -2.0290   -0.4221 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627   -0.7976    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958    0.1325    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0212    1.3056    0.4640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078    1.1335    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3884   -0.1368    0.4485 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0803   -0.7154    0.6003 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9427    0.2498    0.4701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0705   -0.5576    0.5064 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3498    0.2113    0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    0.8868   -0.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9383    1.6911   -0.8795 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.0474    0.6679   -0.6499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0230    2.8326    0.3719 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1591    2.5206   -2.3344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036   -1.5535   -0.5695 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3421   -2.7834   -0.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2751   -1.6719   -0.5125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1228   -2.9684   -0.2440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5688    2.9550   -0.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0792    2.5153    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2214    3.3486    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2093   -3.3833   -1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700    1.9240    1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -1.1688    1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0694   -1.0815    1.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070    0.9536    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807   -0.5216    0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1996    2.4043    1.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1563    2.5589   -2.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1484   -1.2740   -1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9193   -2.6899    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -1.3215   -1.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0903   -3.1556    0.7074 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
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
 14 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  8  3  1  0
 23 12  1  0
 11  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
 10 29  1  0
 12 30  1  1
 14 31  1  1
 15 32  1  0
 15 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  6
 22 37  1  0
 23 38  1  6
 24 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Methylthioinosine-5'-monophosphate	Kegg
6-Methylthioinosine-5'-monophosphoric acid	Generator
6-Methylthiopurine 5'-monophosphoric acid ribonucleotide	Generator
Methylthioinosine-5'-monophospate	HMDB
Methylthioinosine 5'-monophospate	HMDB
MeTIMP	HMDB
6-Methylmercaptopurine ribonucleotide	MeSH
Me-timp	MeSH
MeSPuRMP	MeSH
6-Methylmercaptopurine ribonucleoside-5'-phosphate	MeSH
6-Methylthiopurine ribonucleoside-5'-phosphate	MeSH
Methylthioinosine monophosphate	MeSH

Chemical Formula

C₁₁H₁₅N₄O₇PS

Average Molecular Weight

378.298

Monoisotopic Molecular Weight

378.039906056

IUPAC Name

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(methylsulfanyl)-9H-purin-9-yl]oxolan-2-yl]methoxy}phosphonic acid

Traditional Name

Me-TIMP

CAS Registry Number

7021-52-5

SMILES

CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C11H15N4O7PS/c1-24-10-6-9(12-3-13-10)15(4-14-6)11-8(17)7(16)5(22-11)2-21-23(18,19)20/h3-5,7-8,11,16-17H,2H2,1H3,(H2,18,19,20)/t5-,7-,8-,11-/m1/s1

InChI Key

BMYFUCYXRGTQQL-IOSLPCCCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside monophosphates

Alternative Parents

Substituents

Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
6-thiopurine
Imidazopyrimidine
Purine
Aryl thioether
Alkylarylthioether
Monoalkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Azole
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Azacycle
Oxacycle
Sulfenyl compound
Thioether
Organic oxygen compound
Alcohol
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic molecule (CHEBI:80609 )

Ontology

Not Available

Endogenous (HMDB: HMDB0061339)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Azathioprine Action Pathway (PathBank: SMP0000427)
Mercaptopurine Action Pathway (PathBank: SMP0000428)
Thioguanine Action Pathway (PathBank: SMP0000430)

Metabolic pathway

Mercaptopurine Metabolism Pathway (PathBank: SMP0000609)

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
Water Solubility	2.72 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.1	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.19	ChemAxon
pKa (Strongest Basic)	2.35	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	160.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.13 m³·mol⁻¹	ChemAxon
Polarizability	33.61 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]+	185.156	31661259
DarkChem	[M-H]-	183.557	31661259
DeepCCS	[M+H]+	166.506	30932474
DeepCCS	[M-H]-	164.11	30932474
DeepCCS	[M-2H]-	197.632	30932474
DeepCCS	[M+Na]+	173.431	30932474
AllCCS	[M+H]+	182.0	32859911
AllCCS	[M+H-H2O]+	179.3	32859911
AllCCS	[M+NH4]+	184.5	32859911
AllCCS	[M+Na]+	185.2	32859911
AllCCS	[M-H]-	174.8	32859911
AllCCS	[M+Na-2H]-	174.7	32859911
AllCCS	[M+HCOO]-	174.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Methylthiopurine 5'-monophosphate ribonucleotide	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O	4215.8	Standard polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O	2536.5	Standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O	3331.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Methylthiopurine 5'-monophosphate ribonucleotide,1TMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]1O	3119.4	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,1TMS,isomer #2	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O[Si](C)(C)C	3100.0	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,1TMS,isomer #3	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]1O	3198.3	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,2TMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3019.3	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,2TMS,isomer #2	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	3121.0	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,2TMS,isomer #3	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	3110.0	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,2TMS,isomer #4	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]1O	3169.2	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3100.2	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3242.6	Standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4306.7	Standard polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TMS,isomer #2	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	3148.0	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TMS,isomer #2	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	3241.9	Standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TMS,isomer #2	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	4045.5	Standard polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TMS,isomer #3	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	3138.8	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TMS,isomer #3	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	3242.6	Standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TMS,isomer #3	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	4079.1	Standard polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,4TMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3153.3	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,4TMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3197.2	Standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,4TMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3821.6	Standard polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,1TBDMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3361.6	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,1TBDMS,isomer #2	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3341.5	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,1TBDMS,isomer #3	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O	3425.4	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,2TBDMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3469.6	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,2TBDMS,isomer #2	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3551.8	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,2TBDMS,isomer #3	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3542.7	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,2TBDMS,isomer #4	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O	3571.0	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TBDMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3695.3	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TBDMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3828.2	Standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TBDMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4424.9	Standard polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TBDMS,isomer #2	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3733.6	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TBDMS,isomer #2	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3798.2	Standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TBDMS,isomer #2	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4243.0	Standard polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TBDMS,isomer #3	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3724.4	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TBDMS,isomer #3	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3795.9	Standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,3TBDMS,isomer #3	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4274.4	Standard polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,4TBDMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3901.3	Semi standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,4TBDMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3859.5	Standard non polar	33892256
6-Methylthiopurine 5'-monophosphate ribonucleotide,4TBDMS,isomer #1	CSC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4094.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide GC-MS (Non-derivatized) - 70eV, Positive	splash10-06r2-9522000000-aa3c684c39871b1418eb	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide GC-MS (2 TMS) - 70eV, Positive	splash10-0002-9212210000-ac36694e2001bcdf6ffe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 10V, Positive-QTOF	splash10-014i-0913000000-83e5f1ae357f48429431	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 20V, Positive-QTOF	splash10-014i-0900000000-ccbc23aa8422e91d330b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 40V, Positive-QTOF	splash10-014i-2900000000-ebffe8e04dc10e79a630	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 10V, Negative-QTOF	splash10-004i-7709000000-e13c15aeacbe8d3e18e9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 20V, Negative-QTOF	splash10-00or-9700000000-1b85ddeb6a55a46c6703	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 40V, Negative-QTOF	splash10-004i-9200000000-bf54db28750528a4a182	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 10V, Positive-QTOF	splash10-016r-0907000000-e8f81313b52de4eafa59	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 20V, Positive-QTOF	splash10-014i-0900000000-9a5c4a54c56969eb87a6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 40V, Positive-QTOF	splash10-014i-2900000000-a9737583d6c407a48677	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 10V, Negative-QTOF	splash10-004i-8009000000-7b6d776485a2e2b9a7dd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 20V, Negative-QTOF	splash10-004i-9001000000-171c43fd9d995ec4cf8a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methylthiopurine 5'-monophosphate ribonucleotide 40V, Negative-QTOF	splash10-004i-9100000000-9979f939401e5f72234f	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Mercaptopurine Action Pathway		Not Available
Mercaptopurine Metabolism Pathway		Not Available
Thioguanine Action Pathway		Not Available
Azathioprine Action Pathway		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
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

8266575

KEGG Compound ID

C16615

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10091038

PDB ID

Not Available

ChEBI ID

80609

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
Haglund S, Vikingsson S, Soderman J, Hindorf U, Granno C, Danelius M, Coulthard S, Peterson C, Almer S: The role of inosine-5'-monophosphate dehydrogenase in thiopurine metabolism in patients with inflammatory bowel disease. Ther Drug Monit. 2011 Apr;33(2):200-8. doi: 10.1097/FTD.0b013e31820b42bb. [PubMed:21311411 ]

Enzymes

Enzyme Details

1. Thiopurine S-methyltransferase

General function:: Involved in thiopurine S-methyltransferase activity
Specific function:: Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
Gene Name:: TPMT
Uniprot ID:: P51580
Molecular weight:: 28180.09

Reactions

6-Thioinosine-5'-monophosphate + S-Adenosylmethionine → 6-Methylthiopurine 5'-monophosphate ribonucleotide + S-Adenosylhomocysteine	details

Enzyme Details

2. Hypoxanthine-guanine phosphoribosyltransferase

General function:: Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:: Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:: HPRT1
Uniprot ID:: P00492
Molecular weight:: 24579.155

Reactions

6-Methylmercaptopurine + Phosphoribosyl pyrophosphate → 6-Methylthiopurine 5'-monophosphate ribonucleotide + Pyrophosphate	details

Showing metabocard for 6-Methylthiopurine 5'-monophosphate ribonucleotide (HMDB0060414)

MOL for HMDB0060414 (6-Methylthiopurine 5'-monophosphate ribonucleotide)

3D MOL for HMDB0060414 (6-Methylthiopurine 5'-monophosphate ribonucleotide)

3D SDF for HMDB0060414 (6-Methylthiopurine 5'-monophosphate ribonucleotide)

3D-SDF for HMDB0060414 (6-Methylthiopurine 5'-monophosphate ribonucleotide)

PDB for HMDB0060414 (6-Methylthiopurine 5'-monophosphate ribonucleotide)

3D PDB for HMDB0060414 (6-Methylthiopurine 5'-monophosphate ribonucleotide)

SMILES for HMDB0060414 (6-Methylthiopurine 5'-monophosphate ribonucleotide)

INCHI for HMDB0060414 (6-Methylthiopurine 5'-monophosphate ribonucleotide)

Structure for HMDB0060414 (6-Methylthiopurine 5'-monophosphate ribonucleotide)

3D Structure for HMDB0060414 (6-Methylthiopurine 5'-monophosphate ribonucleotide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions