NP-MRD: Showing NP-Card for Thioguanine (NP0021502)

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Record Information

Version

1.0

Created at

2021-01-06 06:47:09 UTC

Updated at

2021-07-15 17:36:31 UTC

NP-MRD ID

NP0021502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thioguanine

Provided By

NPAtlas

Description

Thioguanine, also known as 6-TG or 2-amino 6MP, belongs to the class of organic compounds known as purinethiones. These are purines in which the purine moiety bears a thioketone. Thioguanine is a drug which is used for remission induction and remission consolidation treatment of acute nonlymphocytic leukemias. In humans, thioguanine is involved in the thioguanine metabolism pathway. Thioguanine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Thioguanine is found in Paris polyphylla and Pseudomonas sp.. It was first documented in 1971 (PMID: 4931964). Based on a literature review a significant number of articles have been published on Thioguanine (PMID: 21803983) (PMID: 22178190) (PMID: 22245861) (PMID: 22261533).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105163D          

 16 17  0  0  0  0            999 V2000
   -3.1404   -0.1472    0.0951 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7338    0.0842    0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2086    1.3061   -0.1023 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141    1.5407   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7398    3.0388   -0.3279 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0099    0.4792   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532    0.3947   -0.1089 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455   -0.9037    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5213   -1.6241    0.1146 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757   -0.7854    0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8736   -0.9496    0.1130 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6984   -0.5644   -0.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6705    0.1255    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089    1.2196   -0.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6764   -1.2823    0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -1.9322    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  2  1  0  0  0  0
 10  6  2  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 15  1  0  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N([H])C1=NC(=S)C2=C(N=C([H])N2[H])N1[H]

> <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_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
15.64558088462347

> <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>
13.243875800097126

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.527836493530447

> <JCHEM_PKA_STRONGEST_BASIC>
3.3125164500323323

> <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

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0      -3.140  -0.147   0.095  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.734   0.084   0.034  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.209   1.306  -0.102  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.114   1.541  -0.162  0.00  0.00           C+0
HETATM    5  S   UNK     0       0.740   3.039  -0.328  0.00  0.00           S+0
HETATM    6  C   UNK     0       1.010   0.479  -0.081  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.353   0.395  -0.109  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.646  -0.904   0.012  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.521  -1.624   0.115  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.476  -0.785   0.060  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.874  -0.950   0.113  0.00  0.00           N+0
HETATM   12  H   UNK     0      -3.698  -0.564  -0.656  0.00  0.00           H+0
HETATM   13  H   UNK     0      -3.671   0.126   0.976  0.00  0.00           H+0
HETATM   14  H   UNK     0       3.009   1.220  -0.209  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.676  -1.282   0.022  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.220  -1.932   0.220  0.00  0.00           H+0
CONECT    1    2   12   13                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    6                                                  
CONECT   11   10    2   16                                                  
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Amino 6MP	ChEBI
2-Amino-1,7-dihydro-6H-purine-6-thione	ChEBI
2-Amino-1,9-dihydropurine-6-thione	ChEBI
2-Amino-6-mercaptopurine	ChEBI
2-Amino-6-merkaptopurin	ChEBI
2-Amino-6-purinethiol	ChEBI
2-Aminopurin-6-thiol	ChEBI
2-Aminopurine-6(1H)-thione	ChEBI
2-Aminopurine-6-thiol	ChEBI
6-Mercapto-2-aminopurine	ChEBI
6-Mercaptoguanine	ChEBI
6-TG	ChEBI
6-Thioguanine	ChEBI
TG	ChEBI
ThG	ChEBI
Tioguanin	ChEBI
Tioguanina	ChEBI
Tioguaninum	ChEBI
Lanvis	Kegg
6 Thioguanine	HMDB
Glaxo wellcome brand OF thioguanine	HMDB
GlaxoSmithKline brand OF thioguanine	HMDB
ThioguaninGSK	HMDB
Thioguanine hemihydrate	HMDB
Tioguanina wellcome	HMDB
Wellcome brand OF thioguanine	HMDB
2 Amino 6 purinethiol	HMDB
GlaxoSmithKline brand OF tioguanine	HMDB
Thioguanine tabloid	HMDB
Glaxo wellcome brand OF tioguanine	HMDB
Tabloid	HMDB
Thioguanine anhydrous	HMDB
Anhydrous, thioguanine	HMDB
Thioguanin GSK	HMDB
Thioguanin-GSK	HMDB
Thioguanine monosodium salt	HMDB
Tioguanine glaxosmithkline brand	HMDB
Thioguanine	ChEBI

Chemical Formula

C₅H₅N₅S

Average Mass

167.1920 Da

Monoisotopic Mass

167.02657 Da

IUPAC Name

2-amino-6,7-dihydro-3H-purine-6-thione

Traditional Name

thioguanine

CAS Registry Number

Not 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 Key

WYWHKKSPHMUBEB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Paris polyphylla	LOTUS Database	35616633
Pseudomonas sp.	NPAtlas	4931964

Species Where Detected

Species Name	Source	Reference
Pseudomonas sp. GH. (HLR 186B)	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purinethiones. These are purines in which the purine moiety bears a thioketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purinethiones

Alternative Parents

Substituents

Purinethione
Aminopyrimidine
Pyrimidinethione
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Azacycle
Organopnictogen compound
Primary amine
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

2-aminopurines (CHEBI:9555 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.36	ALOGPS
logP	-0.35	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.53	ChemAxon
pKa (Strongest Basic)	3.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.09 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.89 m³·mol⁻¹	ChemAxon
Polarizability	15.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA015811

HMDB ID

HMDB0014496

DrugBank ID

DB00352

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Thioguanine

METLIN ID

Not Available

PubChem Compound

2723601

PDB ID

DX4

ChEBI ID

9555

Good Scents ID

Not Available

References

General References

Scannel JP, Pruess DL, Kellett M, Demny TC, Stempel A: Antimetabolites produced by microorganisms. 3. 2-aminopurine-6-thiol (thioguanine). J Antibiot (Tokyo). 1971 May;24(5):328-9. doi: 10.7164/antibiotics.24.328. [PubMed:4931964 ]
Kalra S, Zhang Y, Knatko EV, Finlayson S, Yamamoto M, Dinkova-Kostova AT: Oral azathioprine leads to higher incorporation of 6-thioguanine in DNA of skin than liver: the protective role of the Keap1/Nrf2/ARE pathway. Cancer Prev Res (Phila). 2011 Oct;4(10):1665-74. doi: 10.1158/1940-6207.CAPR-11-0137. Epub 2011 Jul 29. [PubMed:21803983 ]
Jacobsen JH, Schmiegelow K, Nersting J: Liquid chromatography-tandem mass spectrometry quantification of 6-thioguanine in DNA using endogenous guanine as internal standard. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jan 15;881-882:115-8. doi: 10.1016/j.jchromb.2011.11.032. Epub 2011 Nov 28. [PubMed:22178190 ]
Martinez-Fernandez L, Gonzalez L, Corral I: An ab initio mechanism for efficient population of triplet states in cytotoxic sulfur substituted DNA bases: the case of 6-thioguanine. Chem Commun (Camb). 2012 Feb 18;48(15):2134-6. doi: 10.1039/c2cc15775f. Epub 2012 Jan 16. [PubMed:22245861 ]
van Asseldonk DP, Seinen ML, de Boer NK, van Bodegraven AA, Mulder CJ: Hepatotoxicity associated with 6-methyl mercaptopurine formation during azathioprine and 6-mercaptopurine therapy does not occur on the short-term during 6-thioguanine therapy in IBD treatment. J Crohns Colitis. 2012 Feb;6(1):95-101. doi: 10.1016/j.crohns.2011.07.009. [PubMed:22261533 ]

Showing NP-Card for Thioguanine (NP0021502)

MOL for NP0021502 (Thioguanine)

3D MOL for NP0021502 (Thioguanine)

3D SDF for NP0021502 (Thioguanine)

3D-SDF for NP0021502 (Thioguanine)

PDB for NP0021502 (Thioguanine)

3D PDB for NP0021502 (Thioguanine)

SMILES for NP0021502 (Thioguanine)

INCHI for NP0021502 (Thioguanine)

Structure for NP0021502 (Thioguanine)

3D Structure for NP0021502 (Thioguanine)