Showing metabocard for Thioguanine (MMDBc0016011)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-05-15 06:44:01 UTC
Update Date2022-08-31 06:40:14 UTC
Metabolite IDMMDBc0016011
Metabolite Identification
Common NameThioguanine
DescriptionThioguanine is only found in individuals that have used or taken this drug. It is an antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia. [PubChem]Thioguanine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to 6-thioguanilyic acid (TGMP), which reaches high intracellular concentrations at therapeutic doses. TGMP interferes with the synthesis of guanine nucleotides by its inhibition of purine biosynthesis by pseudofeedback inhibition of glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway of purine ribonucleotide synthesis. TGMP also inhibits the conversion of inosinic acid (IMP) to xanthylic acid (XMP) by competition for the enzyme IMP dehydrogenase. Thioguanine nucleotides are incorporated into both the DNA and the RNA by phosphodiester linkages, and some studies have shown that incorporation of such false bases contributes to the cytotoxicity of thioguanine. Its tumor inhibitory properties may be due to one or more of its effects on feedback inhibition of de novo purine synthesis; inhibition of purine nucleotide interconversions; or incorporation into the DNA and RNA. The overall result of its action is a sequential blockade of the utilization and synthesis of the purine nucleotides.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000560be1f75380>

2723601
  Mrv0541 02231214372D          

 11 12  0  0  0  0            999 V2000
    3.5220    1.4933    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.9818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171    0.5071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -0.8206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.2558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.9818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3  7  1  0  0  0  0
  3 11  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x0000560be1f75380>

HMDB0014496
     RDKit          3D
Thioguanine
 16 17  0  0  0  0  0  0  0  0999 V2000
    3.1464   -0.1706   -0.0033 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7463    0.0566    0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2187    1.2911    0.2275 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1077    1.5093    0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481    2.9920    0.4988 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006    0.4685    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    0.4225    0.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6537   -0.8628   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360   -1.6057   -0.2939 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4677   -0.7841   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8586   -0.9401   -0.1569 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -0.4110   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -0.0908    0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0325    1.2140    0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6946   -1.1997   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -1.8894   -0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
 10  6  2  0
  1 12  1  0
  1 13  1  0
  7 14  1  0
  8 15  1  0
 11 16  1  0
M  END
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3D SDF for #<Metabolite:0x0000560be1f75380>

2723601
  Mrv0541 02231214372D          

 11 12  0  0  0  0            999 V2000
    3.5220    1.4933    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.9818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171    0.5071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -0.8206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.2558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.9818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3  7  1  0  0  0  0
  3 11  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016011

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC(=S)C2=C(N1)N=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

> <INCHI_KEY>
WYWHKKSPHMUBEB-UHFFFAOYSA-N

> <FORMULA>
C5H5N5S

> <MOLECULAR_WEIGHT>
167.192

> <EXACT_MASS>
167.026565875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.645580884623488

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6,7-dihydro-3H-purine-6-thione

> <ALOGPS_LOGP>
-0.36

> <JCHEM_LOGP>
-0.34946934999999996

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.254381575136076

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.526449965810505

> <JCHEM_PKA_STRONGEST_BASIC>
3.7004519894928056

> <JCHEM_POLAR_SURFACE_AREA>
79.09

> <JCHEM_REFRACTIVITY>
46.891999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thioguanine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000560be1f75380>

HMDB0014496
     RDKit          3D
Thioguanine
 16 17  0  0  0  0  0  0  0  0999 V2000
    3.1464   -0.1706   -0.0033 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7463    0.0566    0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2187    1.2911    0.2275 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1077    1.5093    0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481    2.9920    0.4988 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0006    0.4685    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    0.4225    0.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6537   -0.8628   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360   -1.6057   -0.2939 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4677   -0.7841   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8586   -0.9401   -0.1569 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080   -0.4110   -0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -0.0908    0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0325    1.2140    0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6946   -1.1997   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -1.8894   -0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
 10  6  2  0
  1 12  1  0
  1 13  1  0
  7 14  1  0
  8 15  1  0
 11 16  1  0
M  END
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PDB for #<Metabolite:0x0000560be1f75380>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2723601                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.574   2.787   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0       6.574  -1.833   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.365   0.947   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.365  -1.532   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.241   0.477   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       3.907  -1.833   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.908   0.477   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.908  -1.063   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.574   1.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -1.063   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.264  -0.293   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    8   10                                                       
CONECT    3    7   11                                                       
CONECT    4    8   11                                                       
CONECT    5    9   10                                                       
CONECT    6   10                                                            
CONECT    7    3    8    9                                                  
CONECT    8    2    4    7                                                  
CONECT    9    1    5    7                                                  
CONECT   10    2    5    6                                                  
CONECT   11    3    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for #<Metabolite:0x0000560be1f75380>

COMPND    HMDB0014496
HETATM    1  N1  UNL     1       3.146  -0.171  -0.003  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.746   0.057   0.022  1.00  0.00           C  
HETATM    3  N2  UNL     1       1.219   1.291   0.228  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.108   1.509   0.252  1.00  0.00           C  
HETATM    5  S1  UNL     1      -0.748   2.992   0.499  1.00  0.00           S  
HETATM    6  C3  UNL     1      -1.001   0.469   0.065  1.00  0.00           C  
HETATM    7  N3  UNL     1      -2.353   0.423   0.044  1.00  0.00           N  
HETATM    8  C4  UNL     1      -2.654  -0.863  -0.178  1.00  0.00           C  
HETATM    9  N4  UNL     1      -1.536  -1.606  -0.294  1.00  0.00           N  
HETATM   10  C5  UNL     1      -0.468  -0.784  -0.143  1.00  0.00           C  
HETATM   11  N5  UNL     1       0.859  -0.940  -0.157  1.00  0.00           N  
HETATM   12  H1  UNL     1       3.708  -0.411  -0.843  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.661  -0.091   0.896  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.032   1.214   0.173  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.695  -1.200  -0.246  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.254  -1.889  -0.315  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    3   11
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   10   10
CONECT    7    8   14
CONECT    8    9    9   15
CONECT    9   10
CONECT   10   11
CONECT   11   16
END
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SMILES for #<Metabolite:0x0000560be1f75380>

NC1=NC(=S)C2=C(N1)N=CN2
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INCHI for #<Metabolite:0x0000560be1f75380>

InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
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Synonyms
ValueSource
2-Amino 6MPChEBI
2-Amino-1,7-dihydro-6H-purine-6-thioneChEBI
2-Amino-1,9-dihydropurine-6-thioneChEBI
2-Amino-6-mercaptopurineChEBI
2-Amino-6-merkaptopurinChEBI
2-Amino-6-purinethiolChEBI
2-Aminopurin-6-thiolChEBI
2-Aminopurine-6(1H)-thioneChEBI
2-Aminopurine-6-thiolChEBI
6-Mercapto-2-aminopurineChEBI
6-MercaptoguanineChEBI
6-TGChEBI
6-ThioguanineChEBI
TGChEBI
ThGChEBI
TioguaninChEBI
TioguaninaChEBI
TioguaninumChEBI
LanvisKegg
6 ThioguanineHMDB
Glaxo wellcome brand OF thioguanineHMDB
GlaxoSmithKline brand OF thioguanineHMDB
ThioguaninGSKHMDB
Thioguanine hemihydrateHMDB
Tioguanina wellcomeHMDB
Wellcome brand OF thioguanineHMDB
2 Amino 6 purinethiolHMDB
GlaxoSmithKline brand OF tioguanineHMDB
Thioguanine tabloidHMDB
Glaxo wellcome brand OF tioguanineHMDB
TabloidHMDB
Thioguanine anhydrousHMDB
Anhydrous, thioguanineHMDB
Thioguanin GSKHMDB
Thioguanin-GSKHMDB
Thioguanine monosodium saltHMDB
Tioguanine glaxosmithkline brandHMDB
ThioguanineChEBI
Molecular FormulaC5H5N5S
Average Mass167.192
Monoisotopic Mass167.026565875
IUPAC Name2-amino-6,7-dihydro-3H-purine-6-thione
Traditional Namethioguanine
CAS Registry NumberNot Available
SMILES
NC1=NC(=S)C2=C(N1)N=CN2
InChI Identifier
InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI KeyWYWHKKSPHMUBEB-UHFFFAOYSA-N