6-Mercaptopurine (CED0002313)

Record Information
Version1.0
Creation Date2016-05-20 16:10:16 UTC
Update Date2026-05-14 16:56:21 UTC
Accession NumberCHEM016001
Identification
Common Name6-Mercaptopurine
ClassSmall Molecule
Description
6-Mercaptopurine is an organic compound with the formula C5H4N4S and an average molecular weight of 152.18 g/mol. 6-Mercaptopurine belongs to the purines and purine derivatives, a subclass of imidazopyrimidines within the organic compounds. The compound is found in or released from 15 recorded sources. These include healthcare, pharmaceuticals, and veterinary products, specifically antineoplastic agents and drugs for obstructive airway diseases. It is also associated with electrical and electronic equipment, such as amplifiers, antennas, coils, electric hearing aids, and line transmission systems, among three others. Other sources include food, food processing, and cookware, specifically the processing of fish and meats, as well as building and construction materials like ceilings. Additionally, it is found in household items such as credit card holders and household cleaning and consumer products, including soap dispensers. The recorded route of exposure for this compound is oral. Biologically, 6-Mercaptopurine acts on four recorded protein targets. It functions as an inhibitor of hypoxanthine-guanine phosphoribosyltransferase (HPRT1), amidophosphoribosyltransferase (PPAT), inosine-5'-monophosphate dehydrogenase 1 (IMPDH1), and inosine-5'-monophosphate dehydrogenase 2 (IMPDH2).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
1,7-Dihydro-6H-purine-6-thioneChEBI
3H-Purine-6-thiolChEBI
6-MPChEBI
6-ThiohypoxanthineChEBI
Mercaptopurine anhydrousKegg
PurinetholKegg
6 MPHMDB
6-MercaptopurineHMDB
Mercaptopurine monohydrateHMDB
MercapurinHMDB
MPHMDB
6 Mercaptopurine monohydrateHMDB
6-Mercaptopurine monohydrateHMDB
Puri-netholHMDB
6 MercaptopurineHMDB
GlaxoSmithKline brand OF 6 mercaptopurineHMDB
LeupurinHMDB
Wellcome brand OF 6-mercaptopurineHMDB
6 ThiohypoxanthineHMDB
6 ThiopurineHMDB
Glaxo wellcome brand OF 6 mercaptopurineHMDB
GlaxoSmithKline brand OF 6-mercaptopurineHMDB
Puri netholHMDB
Wellcome brand OF 6 mercaptopurineHMDB
6-ThiopurineHMDB
Glaxo wellcome brand OF 6-mercaptopurineHMDB
Mercaptopurina wellcomeHMDB
PurimetholHMDB
Chemical FormulaC5H4N4S
Average Molecular Mass152.177 g/mol
Monoisotopic Mass152.016 g/mol
CAS Registry Number50-44-2
IUPAC Name6,7-dihydro-3H-purine-6-thione
Traditional Namemercaptopurine
SMILESS=C1N=CNC2=C1NC=N2
InChI IdentifierInChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChI KeyGLVAUDGFNGKCSF-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
  • Pyrimidinethione
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.74 g/LALOGPS
logP-0.13ALOGPS
logP-0.12ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)2.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.6 m³·mol⁻¹ChemAxon
Polarizability14.04 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0udi-6900000000-6a7f989ad4995b3bfb3bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-80fade3542b1b7a4f542Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-4900000000-ae3cab845511e09fd7d8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052f-9400000000-eb3a9e5b93f0954dda1fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-066u-9300000000-e920208db376745577aeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014r-9100000000-9452425dda09b342a804Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-fb1e1ed0d15536d940b5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9300000000-ae82c485895af50f18e0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ba-9700000000-70542617d846459d1edbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kb-9400000000-34922db319d482f338c7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-7de65dacfd12ff92f5e4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-f85c1903d3c0e56417e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-ea506d4c3735e8341ab4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-f8b71bfd941d3b3f3373Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-7a22823f32dc64d60c70Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-3dac1862e412a02b04c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ufr-7900000000-86f3475856644175beb5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-65499423bcb28e8ec450Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uk9-0900000000-e72e8a55b92000661bf6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01b9-9600000000-b86d5a7c7cd083d92e19Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-67dad22e2593a56a8777Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-804445f5cb6f103d3d1dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-067i-9200000000-91b7dfe5d6dabda4e777Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-cbc84ccd8657a0abcedcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-4900000000-63ec34a1f43cd509d6efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-9000000000-d4dd4afbcb5bdd8e05b5Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
401.0Log mg/kg[230:710]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
391Drugs for obstructive airway diseasesHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
532SelectorsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
572Credit Card HoldersHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
590Lifeboat EquipmentMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
8 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAdenosine receptor A1P47745Cavia porcellusPredicted (SEA)67.9624
Adenosine receptor A2b structureClick to view 3D structureAdenosine receptor A2bP29275HumansPredicted (SEA)593.6
Click to view 3D structureAdenosine receptor A2aP46616Cavia porcellusPredicted (SEA)68.3516
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)519.332
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)1028.54
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)3892.07
Click to view 3D structureAdenosine receptor A2aP30543Rattus norvegicusPredicted (SEA)688.265
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)1924.12
Leucine-rich repeat serine/threonine-protein kinase 2 structureClick to view 3D structureLeucine-rich repeat serine/threonine-protein kinase 2Q5S007HumansPredicted (SEA)3501.19
Click to view 3D structureHistidine kinase 4Q9C5U0Arabidopsis thalianaPredicted (SEA)8.09632
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)6678.53
Click to view 3D structureHistidine kinase 3Q9C5U1Arabidopsis thalianaPredicted (SEA)22.732
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)3124.32
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)5936.55
Click to view 3D structureCytokinin dehydrogenase 2Q9FUJ3Arabidopsis thalianaPredicted (SEA)67.4953
Click to view 3D structureAdenosine receptor A2bP29276Rattus norvegicusPredicted (SEA)484.222
Serine/threonine-protein kinase Chk2 structureClick to view 3D structureSerine/threonine-protein kinase Chk2O96017HumansPredicted (SEA)5608.41
Ribosomal protein S6 kinase alpha-3 structureClick to view 3D structureRibosomal protein S6 kinase alpha-3P51812HumansPredicted (SEA)6458.68
Tyrosine-protein kinase ABL1 structureClick to view 3D structureTyrosine-protein kinase ABL1P00519HumansPredicted (SEA)6744.39
Guanine deaminase structureClick to view 3D structureGuanine deaminaseQ9Y2T3HumansPredicted (SEA)1.47914
Serine/threonine-protein kinase Chk1 structureClick to view 3D structureSerine/threonine-protein kinase Chk1O14757HumansPredicted (SEA)6844.11
Purine nucleoside phosphorylase structureClick to view 3D structurePurine nucleoside phosphorylaseP00491HumansPredicted (SEA)51.5362
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)7279.14
Casein kinase II subunit alpha structureClick to view 3D structureCasein kinase II subunit alphaP68400HumansPredicted (SEA)6654.01
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)4128.42
Concentrations
Not Available
External Links
DrugBank IDDB01033
HMDB IDHMDB0015167
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDPM6
Wikipedia LinkMercaptopurine
Chemspider ID580869
ChEBI ID2208
PubChem Compound ID667490
Kegg Compound IDC02380
YMDB IDNot Available
ECMDB IDM2MDB005637
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24211998
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24651962
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24670805
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24774509