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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:11 UTC
HMDB IDHMDB0014496
Secondary Accession Numbers
  • HMDB14496
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
Data?1676999891
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
Chemical FormulaC5H5N5S
Average Molecular Weight167.192
Monoisotopic Molecular Weight167.026565875
IUPAC Name2-amino-6,7-dihydro-3H-purine-6-thione
Traditional Namethioguanine
CAS Registry Number154-42-7
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purinethiones. These are purines in which the purine moiety bears a thioketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurinethiones
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point> 360 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.83 g/LNot Available
LogP-0.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.83 g/LALOGPS
logP-0.36ALOGPS
logP-0.35ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.53ChemAxon
pKa (Strongest Basic)3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.09 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.89 m³·mol⁻¹ChemAxon
Polarizability15.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.61731661259
DarkChem[M-H]-133.14831661259
DeepCCS[M+H]+133.45330932474
DeepCCS[M-H]-130.16730932474
DeepCCS[M-2H]-167.29830932474
DeepCCS[M+Na]+142.60130932474
AllCCS[M+H]+135.332859911
AllCCS[M+H-H2O]+130.832859911
AllCCS[M+NH4]+139.632859911
AllCCS[M+Na]+140.832859911
AllCCS[M-H]-129.232859911
AllCCS[M+Na-2H]-130.232859911
AllCCS[M+HCOO]-131.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ThioguanineNC1=NC(=S)C2=C(N1)N=CN22943.2Standard polar33892256
ThioguanineNC1=NC(=S)C2=C(N1)N=CN21976.8Standard non polar33892256
ThioguanineNC1=NC(=S)C2=C(N1)N=CN22482.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Thioguanine,1TMS,isomer #1C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]12218.4Semi standard non polar33892256
Thioguanine,1TMS,isomer #1C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]12345.0Standard non polar33892256
Thioguanine,1TMS,isomer #1C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]13298.3Standard polar33892256
Thioguanine,1TMS,isomer #2C[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]22146.7Semi standard non polar33892256
Thioguanine,1TMS,isomer #2C[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]22313.1Standard non polar33892256
Thioguanine,1TMS,isomer #2C[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]23261.3Standard polar33892256
Thioguanine,1TMS,isomer #3C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]22159.2Semi standard non polar33892256
Thioguanine,1TMS,isomer #3C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]22186.2Standard non polar33892256
Thioguanine,1TMS,isomer #3C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]23149.5Standard polar33892256
Thioguanine,2TMS,isomer #1C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C2103.2Semi standard non polar33892256
Thioguanine,2TMS,isomer #1C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C2370.9Standard non polar33892256
Thioguanine,2TMS,isomer #1C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C3054.9Standard polar33892256
Thioguanine,2TMS,isomer #2C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]12250.3Semi standard non polar33892256
Thioguanine,2TMS,isomer #2C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]12226.2Standard non polar33892256
Thioguanine,2TMS,isomer #2C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]12938.7Standard polar33892256
Thioguanine,2TMS,isomer #3C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C2183.3Semi standard non polar33892256
Thioguanine,2TMS,isomer #3C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C2437.5Standard non polar33892256
Thioguanine,2TMS,isomer #3C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C2962.2Standard polar33892256
Thioguanine,2TMS,isomer #4C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C2217.2Semi standard non polar33892256
Thioguanine,2TMS,isomer #4C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C2246.7Standard non polar33892256
Thioguanine,2TMS,isomer #4C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C2965.2Standard polar33892256
Thioguanine,3TMS,isomer #1C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C2186.6Semi standard non polar33892256
Thioguanine,3TMS,isomer #1C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C2242.2Standard non polar33892256
Thioguanine,3TMS,isomer #1C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C2652.2Standard polar33892256
Thioguanine,3TMS,isomer #2C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C2169.1Semi standard non polar33892256
Thioguanine,3TMS,isomer #2C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C2504.2Standard non polar33892256
Thioguanine,3TMS,isomer #2C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C2679.5Standard polar33892256
Thioguanine,3TMS,isomer #3C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C2240.6Semi standard non polar33892256
Thioguanine,3TMS,isomer #3C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C2238.9Standard non polar33892256
Thioguanine,3TMS,isomer #3C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C2718.4Standard polar33892256
Thioguanine,4TMS,isomer #1C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C2264.2Semi standard non polar33892256
Thioguanine,4TMS,isomer #1C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C2320.6Standard non polar33892256
Thioguanine,4TMS,isomer #1C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C2468.0Standard polar33892256
Thioguanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]12431.4Semi standard non polar33892256
Thioguanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]12566.3Standard non polar33892256
Thioguanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]13338.2Standard polar33892256
Thioguanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]22385.6Semi standard non polar33892256
Thioguanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]22548.2Standard non polar33892256
Thioguanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]23267.0Standard polar33892256
Thioguanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]22402.7Semi standard non polar33892256
Thioguanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]22400.8Standard non polar33892256
Thioguanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]23229.6Standard polar33892256
Thioguanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C2506.3Semi standard non polar33892256
Thioguanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C2847.5Standard non polar33892256
Thioguanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C3061.9Standard polar33892256
Thioguanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]12588.8Semi standard non polar33892256
Thioguanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]12593.0Standard non polar33892256
Thioguanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]13018.6Standard polar33892256
Thioguanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C2567.7Semi standard non polar33892256
Thioguanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C2913.8Standard non polar33892256
Thioguanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C2975.7Standard polar33892256
Thioguanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C(C)(C)C2602.1Semi standard non polar33892256
Thioguanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C(C)(C)C2644.8Standard non polar33892256
Thioguanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C(C)(C)C3020.6Standard polar33892256
Thioguanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C2718.6Semi standard non polar33892256
Thioguanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C2860.7Standard non polar33892256
Thioguanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C2835.0Standard polar33892256
Thioguanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2729.8Semi standard non polar33892256
Thioguanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3160.6Standard non polar33892256
Thioguanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2819.6Standard polar33892256
Thioguanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C2797.9Semi standard non polar33892256
Thioguanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C2854.6Standard non polar33892256
Thioguanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C2879.3Standard polar33892256
Thioguanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2950.3Semi standard non polar33892256
Thioguanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3101.9Standard non polar33892256
Thioguanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2804.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Thioguanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-4900000000-d9b2da47228aaa85556a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thioguanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thioguanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 90V, Negative-QTOFsplash10-014i-9300000000-cbba0d635918d03d8b2e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 45V, Negative-QTOFsplash10-001i-1900000000-ec9120f0aa3a2ea840602021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 60V, Negative-QTOFsplash10-001i-2900000000-4050d4a4a73935d7865c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 75V, Negative-QTOFsplash10-00lr-8900000000-d82747e1ca135bce8a182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 30V, Negative-QTOFsplash10-00lr-0900000000-811eb76446c5cb3d13bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 15V, Negative-QTOFsplash10-00lr-0900000000-4d8f4082707719cd5d042021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 75V, Positive-QTOFsplash10-0ue9-0900000000-98689cd23c829bc3ef982021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 90V, Positive-QTOFsplash10-0zgi-2900000000-df4f1659bf9a0fa9e4c22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 45V, Positive-QTOFsplash10-014i-0900000000-9110b43ff3c8ed0028432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 60V, Positive-QTOFsplash10-0uxr-0900000000-3a1c799a60e88b9de1272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 30V, Positive-QTOFsplash10-014i-0900000000-c4db837d0a7e413fc9e72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioguanine 15V, Positive-QTOFsplash10-014i-0900000000-195639211a5dd07a4cf12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 10V, Negative-QTOFsplash10-014i-0900000000-f711c8fa62d6eed053b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 20V, Negative-QTOFsplash10-0159-2900000000-afd9900ecc0fd78faf882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 40V, Negative-QTOFsplash10-014i-9300000000-2ef0a5c247f78f7847a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 10V, Negative-QTOFsplash10-014i-0900000000-4e59f276b6876f830b902021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 20V, Negative-QTOFsplash10-0a4i-9800000000-76282c4c7f26457ec3f92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 40V, Negative-QTOFsplash10-066r-9100000000-310b12df78498951fb542021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 10V, Positive-QTOFsplash10-014i-0900000000-c1b1c192793adf5933a92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 20V, Positive-QTOFsplash10-014i-0900000000-379c32e68ff490bc5f5c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 40V, Positive-QTOFsplash10-0a59-9700000000-757c534cc2a9d57cf0552016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 10V, Positive-QTOFsplash10-014i-0900000000-c0ee1b32f4e590209c562021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 20V, Positive-QTOFsplash10-014i-0900000000-800eeaab9deb1a1ba9ae2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioguanine 40V, Positive-QTOFsplash10-066r-7900000000-43adeb7fa61eea70589c2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00352 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00352 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00352
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00018807
Chemspider ID2005804
KEGG Compound IDC07648
BioCyc IDCPD-5721
BiGG IDNot Available
Wikipedia LinkThioguanine
METLIN IDNot Available
PubChem Compound2723601
PDB IDDX4
ChEBI ID9555
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). FDA label . .

Enzymes

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
Thioguanine + Phosphoribosyl pyrophosphate → 6-Thioguanosine monophosphate + Pyrophosphatedetails
References
  1. Shivashankar K, Subbayya IN, Balaram H: Development of a bacterial screen for novel hypoxanthine-guanine phosphoribosyltransferase substrates. J Mol Microbiol Biotechnol. 2001 Oct;3(4):557-62. [PubMed:11545274 ]
  2. Horikawa K, Kawaguchi T, Ishihara S, Nagakura S, Hidaka M, Kagimoto T, Mitsuya H, Nakakuma H: Frequent detection of T cells with mutations of the hypoxanthine-guanine phosphoribosyl transferase gene in patients with paroxysmal nocturnal hemoglobinuria. Blood. 2002 Jan 1;99(1):24-9. [PubMed:11756148 ]
  3. Fuscoe JC, Zimmerman LJ, Fekete A, Setzer RW, Rossiter BJ: Analysis of X-ray-induced HPRT mutations in CHO cells: insertion and deletions. Mutat Res. 1992 Oct;269(2):171-83. [PubMed:1383700 ]
  4. Elgemeie GH: Thioguanine, mercaptopurine: their analogs and nucleosides as antimetabolites. Curr Pharm Des. 2003;9(31):2627-42. [PubMed:14529546 ]
  5. Suzuki M, Tsuruoka C, Kanai T, Kato T, Yatagai F, Watanabe M: Qualitative and quantitative difference in mutation induction between carbon- and neon-ion beams in normal human cells. Biol Sci Space. 2003 Dec;17(4):302-6. [PubMed:15136753 ]

Transporters

General function:
Involved in ATP binding
Specific function:
May be an organic anion pump relevant to cellular detoxification
Gene Name:
ABCC4
Uniprot ID:
O15439
Molecular weight:
149525.3
References
  1. Bai J, Lai L, Yeo HC, Goh BC, Tan TM: Multidrug resistance protein 4 (MRP4/ABCC4) mediates efflux of bimane-glutathione. Int J Biochem Cell Biol. 2004 Feb;36(2):247-57. [PubMed:14643890 ]