Compounds > 9-deazaguanine
Page last updated: 2024-10-15

9-deazaguanine

Cross-References

ID SourceID
PubMed CID135461003
CHEMBL ID367746
SCHEMBL ID4872325
SCHEMBL ID1715820
MeSH IDM0206370

Synonyms (42)

Synonym
nsc344522
65996-58-9
nsc-344522
9-deazaguanine
9DG ,
DB04356
2-amino-3,5-dihydro-pyrrolo[3,2-d]pyrimidin-4-one
2-amino-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
AKOS000320629
2-amino-1,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
bdbm50108005
CHEMBL367746 ,
A835298
2-amino-3h-pyrrolo[3,2-d]pyrimidin-4(5h)-one
4h-pyrrolo(3,2-d)pyrimidin-4-one, 2-amino-1,5-dihydro-
2-amino-3,5-dihydro-4h-pyrrolo(3,2-d)pyrimidine-4-one
unii-h2o1dd3can
h2o1dd3can ,
nsc 344522
AKOS006329593
4h-pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro-
FT-0649229
4h-pyrrolo[3,2-d]pyrimidin-4-one,2-amino-3,5-dihydro-
SCHEMBL4872325
SCHEMBL1715820
2-amino-1,5-dihydro-4h-pyrrolo[3,2-d]pyrimidin-4-one #
2-amino-3,5-dihydropyrrolo(3,2-d)pyrimidin-4-one
W-203443
DTXSID20216202
mfcd09540493
2-amino-3,5-dihydro-4h-pyrrolo[3,2-d]pyrimidin-4-one
DS-10645
2-amino-1,5-dihydro-4h-pyrrolo(3,2-d)pyrimidin-4-one
4h-pyrrolo(3,2-d)pyrimidin-4-one, 2-amino-3,5-dihydro-
2-amino-3,5-dihydro-4h-pyrrolo(3,2-d)pyrimidin-4-one
SB38177
Q27457004
CS-0079471
2-amino-1,5-dihydro-4h-pyrrolo[3,2-d]pyrimidin-4-one
2-amino-3 pound not5-dihydropyrrolo[3 pound not2-d]pyrimidin-4-one
PD057040
HY-121106

Bioavailability

ExcerptReference
" Pharmacokinetic analysis of BzDAG in the rat showed it to be 48% orally bioavailable (at a dose of 5 mg/kg)."( Purine nucleoside phosphorylase inhibitors: biochemical and pharmacological studies with 9-benzyl-9-deazaguanine and related compounds.
Allan, PW; Bennett, LL; Erion, MD; Montgomery, JA; Niwas, S; Noker, PE; Rose, LM, 1993)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

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)
Purine nucleoside phosphorylase Bos taurus (cattle)Kd0.16500.00000.66673.3000AID694065; AID694066
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Purine nucleoside phosphorylase Bos taurus (cattle)Kieq7.40000.00003.47507.4000AID694063
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
purine ribonucleoside salvagePurine nucleoside phosphorylase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
purine-nucleoside phosphorylase activityPurine nucleoside phosphorylase Bos taurus (cattle)
guanosine phosphorylase activityPurine nucleoside phosphorylase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID694063Inhibition of bovine PNP using 7-methylguanosine as substrate by spectrophotometric based coupled assay2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Trimeric purine nucleoside phosphorylase: exploring postulated one-third-of-the-sites binding in the transition state.
AID1767038Inhibition of hexa-his tagged Helicobacter pylori XGHPRT using guanine and PRib-PP as substrate2021Journal of medicinal chemistry, 05-13, Volume: 64, Issue:9
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.
AID694065Binding affinity to calf recombinant PNP expressed in Escherichia coli BL21 (DE3) by fluorimetric titration analysis2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Trimeric purine nucleoside phosphorylase: exploring postulated one-third-of-the-sites binding in the transition state.
AID694066Binding affinity to calf recombinant PNP expressed in Escherichia coli BL21 (DE3) by isothermal titration calorimetry2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Trimeric purine nucleoside phosphorylase: exploring postulated one-third-of-the-sites binding in the transition state.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's6 (37.50)18.2507
2000's4 (25.00)29.6817
2010's5 (31.25)24.3611
2020's1 (6.25)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 (%)
Trials1 (5.88%)5.53%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (88.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
cytosine
[no description available]		2.0310aminopyrimidine;
pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae 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.		2.0110xanthineSaccharomyces cerevisiae metabolite
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		2.1110amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		1.9810pyrrole;
secondary amine
thiophenes
Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.		1.9810mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent
clodronic acid
Clodronic Acid: A diphosphonate which affects calcium metabolism. It inhibits bone resorption and soft tissue calcification.. clodronic acid : An organochlorine compound that is methylene chloride in which both hydrogens are replaced by phosphonic acid groups. It inhibits bone resorption and soft tissue calcification, and is used (often as the disodium salt tetrahydrate) as an adjunct in the treatment of severe hypercalcaemia associated with malignancy, and in the management of osteolytic lesions and bone pain associated with skeletal metastases.		2.45201,1-bis(phosphonic acid);
one-carbon compound;
organochlorine compound		antineoplastic agent;
bone density conservation agent
difluoromethylene diphosphonate
difluoromethylene diphosphonate: inhibits bone resorption		2.4520
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.		2.0310oxopurine
organophosphonates
hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.		2.4620divalent inorganic anion;
phosphite ion
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.		2.3110aryl 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		2.3110
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.		2.31102-aminopurinesanticoronaviral agent;
antimetabolite;
antineoplastic agent
6-thioguanosine
6-thioguanosine: RN given refers to cpd without isomeric designation		1.9810purine nucleoside
oligonucleotides
[no description available]		2.0310
deoxyguanosine
[no description available]		1.9810purine 2'-deoxyribonucleoside;
purines 2'-deoxy-D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
deoxyguanosine triphosphate
[no description available]		1.9810deoxyguanosine phosphate;
guanyl deoxyribonucleotide;
purine 2'-deoxyribonucleoside 5'-triphosphate		Arabidopsis thaliana metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
guanine
[no description available]		6.581512-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
guanosine
ribonucleoside : Any nucleoside where the sugar component is D-ribose.		2.3820guanosines;
purines D-ribonucleoside		fundamental metabolite
hypoxanthine
[no description available]		2.0710nucleobase analogue;
oxopurine;
purine nucleobase		fundamental metabolite
inosine
[no description available]		2.3820inosines;
purines D-ribonucleoside		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
pteroic acid
pteroic acid: structure		2.0110pteroic acid
forodesine
forodesine: structure in first source		2.0710dihydroxypyrrolidine;
pyrrolopyrimidine
ci 972
CI 972: structure given in first source		1.9810
2-amino-6-hydroxy-8-mercaptopurine
[no description available]		2.0110
9-deazahypoxanthine
9-deazahypoxanthine: structure in first source		7.1310
9-deaza-9-(3-thienylmethyl)guanine
[no description available]		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Cholera Infantum
[description not available]		02.3110
Infections, Helicobacter
[description not available]		02.3110
Helicobacter Infections
Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.		02.3110
Leucocythaemia
[description not available]		02.0510
Germinoblastoma
[description not available]		02.0510
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		02.0510
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		02.0510
Acquired Immune Deficiency Syndrome
[description not available]		04.2811
Benign Neoplasms
[description not available]		04.2811
Acquired Immunodeficiency Syndrome
An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.		04.2811
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		04.2811
Leukemia L 1210
[description not available]		01.9810
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