Compounds > 2-amino-6-hydroxy-8-mercaptopurine
Page last updated: 2024-10-15

2-amino-6-hydroxy-8-mercaptopurine

Cross-References

ID SourceID
PubMed CID135423614
CHEMBL ID178006
SCHEMBL ID94822
MeSH IDM0511211

Synonyms (49)

Synonym
OPREA1_703445
B55 ,
2-amino-8-sulfanyl-1,9-dihydro-6h-purin-6-one
nsc29188
nsc-29188
6324-72-7
NCGC00161968-01
SR-01000634975-1
HMS1667K04
bdbm50108009
2-amino-8-mercapto-1h-purin-6(9h)-one
2-amino-8-mercapto-1,9-dihydro-purin-6-one
FT-0661842
CHEMBL178006 ,
2-amino-1,7,8,9-tetrahydro-2-thioxo-6h-purin-6-one
einecs 228-686-9
nsc 29188
2-amino-6-hydroxy-8-thiopurine
28128-40-7
AKOS006229987
CCG-45192
2-amino-6-hydroxy-8-mercaptopurine
FT-0611207
SCHEMBL94822
JHEKNTQSGTVPAO-UHFFFAOYSA-N
8-mercaptoguanine
2-amino-8-mercapto-7h-purin-6-ol
AKOS024306764
W-203352
DTXSID50212631
mfcd00075623
AKOS027320780
2-amino-6-oxy-8-thiopurine
bdbm50181897
2-amino-8-mercapto-1,9-dihydro-6h-purin-6-one
6h-purin-6-one,2-amino-1,7,8,9-tetrahydro-8-thioxo-
2-amino-8-thioxo-8,9-dihydro-1h-purin-6(7h)-one
2-amino-8-thioxo-3,7,8,9-tetrahydro-6h-purin-6-one
oxirane,2-[[2,2,2-trifluoro-1-(2,3,5,6-tetrafluorophenyl)-1-(trifluoromethyl)ethoxy]methyl]-
2-amino-8-mercapto-1h-purin-6(7h)-one
2-amino-8-mercapto-9h-purin-6-ol
E78564
Q27458232
BS-51664
2-amino-8-sulfanyl-3,7-dihydropurin-6-one
2-amino-8-sulfanylidene-7,9-dihydro-1h-purin-6-one
EN300-2596716
2-amino-8-sulfanyl-7h-purin-6-ol
Z1198147829
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency31.62280.631035.7641100.0000AID504339
chromobox protein homolog 1Homo sapiens (human)Potency14.12540.006026.168889.1251AID540317
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseEscherichia coli K-12Kd130.00007.50007.50007.5000AID1129829; AID1308277
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
response to xenobiotic stimulusDihydropteroate synthaseEscherichia coli K-12
folic acid biosynthetic processDihydropteroate synthaseEscherichia coli K-12
folic acid-containing compound biosynthetic processDihydropteroate synthaseEscherichia coli K-12
tetrahydrofolate biosynthetic processDihydropteroate synthaseEscherichia coli K-12
folic acid biosynthetic processDihydropteroate synthaseEscherichia coli K-12
folic acid-containing compound biosynthetic process2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseEscherichia coli K-12
tetrahydrofolate biosynthetic process2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseEscherichia coli K-12
folic acid biosynthetic process2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
dihydropteroate synthase activityDihydropteroate synthaseEscherichia coli K-12
transferase activityDihydropteroate synthaseEscherichia coli K-12
metal ion bindingDihydropteroate synthaseEscherichia coli K-12
magnesium ion binding2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseEscherichia coli K-12
2-amino-4-hydroxy-6-hydroxymethyldihydropteridine diphosphokinase activity2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseEscherichia coli K-12
ATP binding2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseEscherichia coli K-12
kinase activity2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
cytoplasmDihydropteroate synthaseEscherichia coli K-12
cytosolDihydropteroate synthaseEscherichia coli K-12
cytosolDihydropteroate synthaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID1129829Binding affinity to GST-tagged Escherichia coli HPPK expressed in Escherichia coli by SPR assay based alternative equilibrium affinity method in presence of AMP-CPP2014Bioorganic & medicinal chemistry, Apr-01, Volume: 22, Issue:7
The identification, analysis and structure-based development of novel inhibitors of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase.
AID66419Inhibitory concentration against Enzymatic A chain of ricin (RTA) using Artemia salina ribosomes2002Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1
Structure-based design and characterization of novel platforms for ricin and shiga toxin inhibition.
AID1129827Inhibition of GST-tagged Escherichia coli HPPK expressed in Escherichia coli using 6-hydroxymethyl-7,8-dihydropterin hydrochloride as substrate at 250 uM after 20 mins by luminescence assay2014Bioorganic & medicinal chemistry, Apr-01, Volume: 22, Issue:7
The identification, analysis and structure-based development of novel inhibitors of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase.
AID1308277Binding affinity to biotinylated Escherichia coli HPPK expressed in Escherichia coli BL21 (DE3) in presence of 1 mM ATP by SPR assay2016Journal of medicinal chemistry, 06-09, Volume: 59, Issue:11
Structural Basis for the Selective Binding of Inhibitors to 6-Hydroxymethyl-7,8-dihydropterin Pyrophosphokinase from Staphylococcus aureus and Escherichia coli.
AID444560Inhibition of Bacillus anthracis DHPS expressed in Escherichia coli BL21 (DE3) after 30 mins2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Structural studies of pterin-based inhibitors of dihydropteroate synthase.
AID1170152Binding affinity to Escherichia coli DHPS by surface plasmon resonance analysis2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Structure-based design and development of functionalized Mercaptoguanine derivatives as inhibitors of the folate biosynthesis pathway enzyme 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase from Staphylococcus aureus.
AID444558Inhibition of Bacillus anthracis DHPS expressed in Escherichia coli BL21 (DE3) at 250 uM after 30 mins2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Structural studies of pterin-based inhibitors of dihydropteroate synthase.
AID1170150Binding affinity to Staphylococcus aureus recombinant HPPK by surface plasmon resonance analysis in presence of ATP2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Structure-based design and development of functionalized Mercaptoguanine derivatives as inhibitors of the folate biosynthesis pathway enzyme 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase from Staphylococcus aureus.
AID1170149Binding affinity to Staphylococcus aureus HPPK by isothermal calorimetry2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Structure-based design and development of functionalized Mercaptoguanine derivatives as inhibitors of the folate biosynthesis pathway enzyme 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase from Staphylococcus aureus.
AID1170151Binding affinity to Staphylococcus aureus recombinant HPPK by surface plasmon resonance analysis2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Structure-based design and development of functionalized Mercaptoguanine derivatives as inhibitors of the folate biosynthesis pathway enzyme 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase from Staphylococcus aureus.
AID1170148Inhibition of Staphylococcus aureus HPPK after 20 mins by luciferase reporter gene assay2014Journal of medicinal chemistry, Nov-26, Volume: 57, Issue:22
Structure-based design and development of functionalized Mercaptoguanine derivatives as inhibitors of the folate biosynthesis pathway enzyme 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase from Staphylococcus aureus.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (18.18)29.6817
2010's8 (72.73)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		2.03106-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
4-aminobenzoic acid
4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.		2.0510aminobenzoic acid;
aromatic amino-acid zwitterion		allergen;
Escherichia coli metabolite;
plant metabolite
uric acid
Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.		2.0310uric acidEscherichia coli metabolite;
human metabolite;
mouse metabolite
xanthine
7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated.. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.		7.4220xanthineSaccharomyces cerevisiae metabolite
glycarbylamide
[no description available]		2.0510
isoguanine
isoguanine: structure. isoguanine : An oxopurine that is 3,7-dihydro-purin-2-one in which the hydrogen at position 6 is substituted by an amino group.		2.110oxopurine
mercaptopurine
Mercaptopurine: 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.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.		7.0310aryl thiol;
purines;
thiocarbonyl compound		anticoronaviral agent;
antimetabolite;
antineoplastic agent
6-thioxanthine
6-thioxanthine: gpt/6-TXenzyme/prodrug pair is a promising alternative to the thymidine kinase gene and ganciclovir combination in the gene therapy of cancer		2.0310
thioguanine anhydrous
Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.		2.46202-aminopurinesanticoronaviral agent;
antimetabolite;
antineoplastic agent
6-thiouric acid
6-thiouric acid: structure		2.0310oxopurine
guanine
[no description available]		2.44202-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
pteroic acid
pteroic acid: structure		2.0110pteroic acid
allopurinol
Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.		2.0310nucleobase analogue;
organic heterobicyclic compound		antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
pterine-6-carboxylic acid
pterine-6-carboxylic acid: photodegradation product of folic acid		2.0510organonitrogen compound;
organooxygen compound
8-methylguanine
8-methylguanine: structure given in first source		2.110
6-methyltetrahydropterin
[no description available]		2.0510pterins
9-deazaguanine
[no description available]		2.0110
ConditionIndicatedRelationship StrengthStudiesTrials
Encephalitis, Polio
[description not available]		02.0610
Poliomyelitis
An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)		02.0610
Plasmodium falciparum Malaria
[description not available]		02.110
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.110
Anemia, Fanconi
[description not available]		02.1310
Fanconi Anemia
Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)		02.1310