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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:06 UTC
HMDB IDHMDB0015167
Secondary Accession Numbers
  • HMDB15167
Metabolite Identification
Common NameMercaptopurine
DescriptionMercaptopurine is only found in individuals that have used or taken this drug. It is an antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia. [PubChem]Mercaptopurine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to thioinosinic acid (TIMP). This intracellular nucleotide inhibits several reactions involving inosinic acid (IMP), including the conversion of IMP to xanthylic acid (XMP) and the conversion of IMP to adenylic acid (AMP) via adenylosuccinate (SAMP). In addition, 6-methylthioinosinate (MTIMP) is formed by the methylation of TIMP. Both TIMP and MTIMP have been reported to inhibit glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway for purine ribonucleotide synthesis. Experiments indicate that radiolabeled mercaptopurine may be recovered from the DNA in the form of deoxythioguanosine. Some mercaptopurine is converted to nucleotide derivatives of 6-thioguanine (6-TG) by the sequential actions of inosinate (IMP) dehydrogenase and xanthylate (XMP) aminase, converting TIMP to thioguanylic acid (TGMP).
Structure
Data?1582753266
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 Weight152.177
Monoisotopic Molecular Weight152.015666838
IUPAC Name6,7-dihydro-3H-purine-6-thione
Traditional Namemercaptopurine
CAS Registry Number50-44-2
SMILES
S=C1N=CNC2=C1NC=N2
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point313 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.74 g/LNot Available
LogP-0.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.74 g/LALOGPS
logP10(-0.13) g/LALOGPS
logP10(-0.12) g/LChemAxon
logS10(-2.3) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.4531661259
DarkChem[M-H]-126.65231661259
DeepCCS[M+H]+125.01630932474
DeepCCS[M-H]-122.87730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MercaptopurineS=C1N=CNC2=C1NC=N22464.4Standard polar33892256
MercaptopurineS=C1N=CNC2=C1NC=N21612.5Standard non polar33892256
MercaptopurineS=C1N=CNC2=C1NC=N22359.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mercaptopurine,1TMS,isomer #1C[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]21933.6Semi standard non polar33892256
Mercaptopurine,1TMS,isomer #1C[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]22087.1Standard non polar33892256
Mercaptopurine,1TMS,isomer #1C[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]22722.5Standard polar33892256
Mercaptopurine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]21871.2Semi standard non polar33892256
Mercaptopurine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]21945.7Standard non polar33892256
Mercaptopurine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]22583.3Standard polar33892256
Mercaptopurine,2TMS,isomer #1C[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C2074.9Semi standard non polar33892256
Mercaptopurine,2TMS,isomer #1C[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C2152.7Standard non polar33892256
Mercaptopurine,2TMS,isomer #1C[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C2394.8Standard polar33892256
Mercaptopurine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]22160.6Semi standard non polar33892256
Mercaptopurine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]22325.9Standard non polar33892256
Mercaptopurine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]22791.6Standard polar33892256
Mercaptopurine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]22111.4Semi standard non polar33892256
Mercaptopurine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]22172.4Standard non polar33892256
Mercaptopurine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]22686.6Standard polar33892256
Mercaptopurine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C(C)(C)C2432.8Semi standard non polar33892256
Mercaptopurine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C(C)(C)C2554.5Standard non polar33892256
Mercaptopurine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C(C)(C)C2529.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mercaptopurine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-6900000000-6a7f989ad4995b3bfb3b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mercaptopurine 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 - Mercaptopurine LC-ESI-QQ , negative-QTOFsplash10-0udi-1900000000-80fade3542b1b7a4f5422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , negative-QTOFsplash10-0udi-4900000000-ae3cab845511e09fd7d82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , negative-QTOFsplash10-052f-9400000000-eb3a9e5b93f0954dda1f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , negative-QTOFsplash10-066u-9300000000-e920208db376745577ae2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , negative-QTOFsplash10-014r-9100000000-9452425dda09b342a8042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , positive-QTOFsplash10-000i-0900000000-fb1e1ed0d15536d940b52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , positive-QTOFsplash10-00di-9300000000-ae82c485895af50f18e02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , positive-QTOFsplash10-01ba-9700000000-70542617d846459d1edb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , positive-QTOFsplash10-00kb-9400000000-34922db319d482f338c72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , positive-QTOFsplash10-0006-9000000000-7de65dacfd12ff92f5e42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine 40V, Positive-QTOFsplash10-014i-0900000000-f85c1903d3c0e56417e12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine 20V, Positive-QTOFsplash10-0udi-0900000000-ea506d4c3735e8341ab42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mercaptopurine 10V, Positive-QTOFsplash10-0udi-0900000000-f8b71bfd941d3b3f33732021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 10V, Positive-QTOFsplash10-0udi-0900000000-7a22823f32dc64d60c702016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 20V, Positive-QTOFsplash10-0udi-0900000000-3dac1862e412a02b04c72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 40V, Positive-QTOFsplash10-0ufr-7900000000-86f3475856644175beb52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 10V, Negative-QTOFsplash10-0udi-0900000000-65499423bcb28e8ec4502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 20V, Negative-QTOFsplash10-0uk9-0900000000-e72e8a55b92000661bf62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 40V, Negative-QTOFsplash10-01b9-9600000000-b86d5a7c7cd083d92e192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 10V, Positive-QTOFsplash10-0udi-0900000000-67dad22e2593a56a87772021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 20V, Positive-QTOFsplash10-0udi-0900000000-804445f5cb6f103d3d1d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 40V, Positive-QTOFsplash10-067i-9200000000-91b7dfe5d6dabda4e7772021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 10V, Negative-QTOFsplash10-0udi-0900000000-cbc84ccd8657a0abcedc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 20V, Negative-QTOFsplash10-0udi-4900000000-63ec34a1f43cd509d6ef2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mercaptopurine 40V, Negative-QTOFsplash10-0aor-9000000000-d4dd4afbcb5bdd8e05b52021-10-11Wishart 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
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 DB01033 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01033 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01033
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID580869
KEGG Compound IDC02380
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMercaptopurine
METLIN IDNot Available
PubChem Compound667490
PDB IDPM6
ChEBI ID2208
Food Biomarker OntologyNot Available
VMH IDM02989
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Reactions
Mercaptopurine + Water + Oxygen → 6-Thiourate + Hydrogen peroxidedetails
References
  1. Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]
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
Mercaptopurine + S-Adenosylmethionine → 6-Methylmercaptopurine + S-Adenosylhomocysteinedetails
References
  1. Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]
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
Mercaptopurine + Phosphoribosyl pyrophosphate → 6-Thioinosine-5'-monophosphate + Pyrophosphatedetails
References
  1. Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]

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. Chen ZS, Lee K, Kruh GD: Transport of cyclic nucleotides and estradiol 17-beta-D-glucuronide by multidrug resistance protein 4. Resistance to 6-mercaptopurine and 6-thioguanine. J Biol Chem. 2001 Sep 7;276(36):33747-54. Epub 2001 Jul 10. [PubMed:11447229 ]
General function:
Involved in ATP binding
Specific function:
Acts as a multispecific organic anion pump which can transport nucleotide analogs
Gene Name:
ABCC5
Uniprot ID:
O15440
Molecular weight:
160658.8
References
  1. Wijnholds J, Mol CA, van Deemter L, de Haas M, Scheffer GL, Baas F, Beijnen JH, Scheper RJ, Hatse S, De Clercq E, Balzarini J, Borst P: Multidrug-resistance protein 5 is a multispecific organic anion transporter able to transport nucleotide analogs. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7476-81. [PubMed:10840050 ]