Compounds > 5-chlorotubercidin
Page last updated: 2024-11-07

5-chlorotubercidin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

5-Chlorotubercidin is a synthetic nucleoside analog of tubercidin, a naturally occurring adenosine analog. It is a potent inhibitor of adenosine deaminase, an enzyme that catalyzes the conversion of adenosine to inosine. This inhibition leads to the accumulation of adenosine, which can have various effects on cellular processes, including immune system modulation. 5-chlorotubercidin has shown potential as an anti-inflammatory agent and as a therapeutic agent for certain types of cancer. Its effects on immune system modulation and potential therapeutic applications continue to be investigated. Its importance lies in its unique structural features and its ability to target key enzymes like adenosine deaminase. This makes it an attractive compound for further research into its pharmacological properties and therapeutic potential.'

Cross-References

ID SourceID
PubMed CID97453
CHEMBL ID98933
SCHEMBL ID20938332
MeSH IDM0091983

Synonyms (12)

Synonym
CHEMBL98933 ,
24386-95-6
5-chlorotubercidin
2-(4-amino-5-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
(2r,3r,4s,5r)-2-(4-amino-5-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
(2r,3r,4s,5r)-2-(4-amino-5-chloro-7h-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol
(2r,3r,4s,5r)-2-(4-amino-5-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
bdbm50090857
nsc 124149
7h-pyrrolo(2,3-d)pyrimidin-4-amine, 5-chloro-7-beta-d-ribofuranosyl-
EKH ,
SCHEMBL20938332
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)IC50 (µMol)4,786,300.00000.00020.552110.0000AID34006
Adenosine receptor A3Rattus norvegicus (Norway rat)IC50 (µMol)4,786,300.00000.00070.03740.0957AID34006
Adenosine receptor A2bRattus norvegicus (Norway rat)IC50 (µMol)4,786,300.00000.00240.68169.0000AID34006
Adenosine receptor A2aRattus norvegicus (Norway rat)IC50 (µMol)4,786,300.00000.00120.48289.0000AID34006
Adenosine kinaseHomo sapiens (human)IC50 (µMol)2,387,652.60500.00050.605210.0000AID33985; AID33990; AID33993; AID34006
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
purine ribonucleoside salvageAdenosine kinaseHomo sapiens (human)
dATP biosynthetic processAdenosine kinaseHomo sapiens (human)
ribonucleoside monophosphate biosynthetic processAdenosine kinaseHomo sapiens (human)
GMP salvageAdenosine kinaseHomo sapiens (human)
AMP salvageAdenosine kinaseHomo sapiens (human)
dAMP salvageAdenosine kinaseHomo sapiens (human)
purine nucleobase metabolic processAdenosine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
RNA bindingAdenosine kinaseHomo sapiens (human)
deoxyadenosine kinase activityAdenosine kinaseHomo sapiens (human)
ATP bindingAdenosine kinaseHomo sapiens (human)
metal ion bindingAdenosine kinaseHomo sapiens (human)
adenosine kinase activityAdenosine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
nucleoplasmAdenosine kinaseHomo sapiens (human)
cytosolAdenosine kinaseHomo sapiens (human)
plasma membraneAdenosine kinaseHomo sapiens (human)
nucleusAdenosine kinaseHomo sapiens (human)
cytosolAdenosine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID1691959Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability incubated for 3 days by MTS assay2020European journal of medicinal chemistry, Jun-01, Volume: 195Anti-norovirus activity of C7-modified 4-amino-pyrrolo[2,1-f][1,2,4]triazine C-nucleosides.
AID91293Cytotoxicity against uninfected human foreskin fibroblast(HFF cells)1988Journal of medicinal chemistry, Nov, Volume: 31, Issue:11
Synthesis and antiviral activity of certain 4- and 4,5-disubstituted 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID90613Inhibitory concentration against human cytomegalovirus (HCMV) in plaque reduction assay1988Journal of medicinal chemistry, Nov, Volume: 31, Issue:11
Synthesis and antiviral activity of certain 4- and 4,5-disubstituted 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID382097Inhibition of adenosine kinase2008Bioorganic & medicinal chemistry, May-01, Volume: 16, Issue:9
A CoMSIA study on the adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues.
AID229232Concentration required to reduce vesicular stomatitis virus induced cytopathogenicity by 50% in primary rabbit kidney cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID34006Concentration required for 50% inhibition of the adenosine kinase (AK) activity.2004Bioorganic & medicinal chemistry letters, Jun-21, Volume: 14, Issue:12
A TOPS-MODE approach to predict adenosine kinase inhibition.
AID225769Concentration required to reduce polio virus type 1 induced cytopathogenicity by 50% in HeLa cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID33993Inhibition concentration against human adenosine kinase2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
QSAR study on adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues using the hansch approach.
AID220035Concentration required to reduce coxsackie virus 4 induced cytopathogenicity by 50% in HeLa cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID229059Concentration required to cause a microscopically detectable alteration in cell morphology in vero cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID167327Concentration required to cause a microscopically detectable alteration in cell morphology in primary rabbit kidney cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID84959Concentration required to reduce HSV-2 (G) induced cytopathogenicity by 50% in primary rabbit kidney cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID96660Dose required to inhibit proliferation of L-1210 Cells by 50%1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID87304Concentration required to cause a microscopically detectable alteration in cell morphology in HeLa cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID83889Concentration required to reduce HSV-1 (KOS) induced cytopathogenicity by 50% in primary rabbit kidney cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID228410Concentration required to reduce reovirus type 1 induced cytopathogenicity by 50% in vero cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID33985Inhibition of recombinant human adenosine kinase2000Journal of medicinal chemistry, Jul-27, Volume: 43, Issue:15
Adenosine kinase inhibitors. 1. Synthesis, enzyme inhibition, and antiseizure activity of 5-iodotubercidin analogues.
AID220038Concentration required to reduce coxsackie virus B4 induced cytopathogenicity by 50% in vero cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID229022Concentration required to reduce vaccinia virus induced cytopathogenicity by 50% in primary rabbit kidney cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID96214Cytotoxicity against human neoplastic cell line(KB cells)1988Journal of medicinal chemistry, Nov, Volume: 31, Issue:11
Synthesis and antiviral activity of certain 4- and 4,5-disubstituted 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID1691962Antiviral activity against murine Norovirus infected in mouse RAW264.7 cells assessed as reduction in virus-induced cytopathic effect incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jun-01, Volume: 195Anti-norovirus activity of C7-modified 4-amino-pyrrolo[2,1-f][1,2,4]triazine C-nucleosides.
AID226343Concentration required to reduce sindbis virus induced cytopathogenicity by 50% in vero cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID33990Inhibition of human adenosine kinase activity2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
QSAR study on adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues using the hansch approach.
AID229230Concentration required to reduce vesicular stomatitis virus induced cytopathogenicity by 50% in HeLa cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID224918Concentration required to reduce parainfluenza virus type 3 induced cytopathogenicity by 50% in vero cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (37.50)18.7374
1990's0 (0.00)18.2507
2000's4 (50.00)29.6817
2010's0 (0.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.37

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.37 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.56 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.37)

All Compounds (24.57)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
tubercidin
Tubercidin: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids.. tubercidin : An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.		2.8840antibiotic antifungal agent;
N-glycosylpyrrolopyrimidine;
ribonucleoside		antimetabolite;
antineoplastic agent;
bacterial metabolite
toyocamycin
Toyocamycin: 4-Amino-5-cyano-7-(D-ribofuranosyl)-7H- pyrrolo(2,3-d)pyrimidine. Antibiotic antimetabolite isolated from Streptomyces toyocaensis cultures. It is an analog of adenosine, blocks RNA synthesis and ribosome function, and is used mainly as a tool in biochemistry.. toyocamycin : An N-glycosylpyrrolopyrimidine that is tubercidin in which the hydrogen at position 5 of the pyrrolopyrimidine moiety has been replaced by a cyano group.		3.150antibiotic antifungal agent;
N-glycosylpyrrolopyrimidine;
nitrile;
ribonucleoside		antimetabolite;
antineoplastic agent;
apoptosis inducer;
bacterial metabolite
nsc 65346
sangivamycin: RN given refers to parent cpd. sangivamycin : A nucleoside analogue that is adenosine in which the nitrogen at position 7 is replaced by a carbamoyl-substituted carbon. It is a potent inhibitor of protein kinase C.		3.150nucleoside analogueprotein kinase inhibitor
n-chlorosuccinimide
N-chlorosuccinimide : A five-membered cyclic dicarboximide compound having a chloro substituent on the nitrogen atom.		1.9510dicarboximide;
pyrrolidinone
ribavirin
Rebetron: Rebetron is tradename		2.41201-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
bromosuccinimide
Bromosuccinimide: A brominating agent that replaces hydrogen atoms in benzylic or allylic positions. It is used in the oxidation of secondary alcohols to ketones and in controlled low-energy brominations. (From Miall's Dictionary of Chemistry, 5th ed; Hawley's Condensed Chemical Dictionary, 12th ed,).		1.9510dicarboximide;
organobromine compound;
pyrrolidinone		reagent
bromotubercidin
[no description available]		3.3770
5-iodotubercidin
7-iodotubercidin: inhibits Toxoplasma gondii adenosine kinase		3.2460organoiodine compound
4-amino-5-bromo-7-(2-hydroxyethoxymethyl)pyrrolo(2,3-d)pyrimidine
4-amino-5-bromo-7-(2-hydroxyethoxymethyl)pyrrolo(2,3-d)pyrimidine: structure given in first source; 5-bromotubercidin in which the ribose is replaced by 2-hydroxyethoxymethyl		1.9710
5'-deoxytoyocamycin
5'-deoxytoyocamycin: from Streptomyces sp. A14345; structure given in first source		2.7130
2'-c-methylcytidine
2'-C-methylcytidine: structure in first source		2.2510
psi 6130
2'-deoxy-2'-fluoro-2'-C-methylcytidine: PSI-6130 is the (beta-D)-isomer; has antiviral activity against hepatitis C virus; structure in first source		2.2510
5'-amino-5'-deoxyadenosine
[no description available]		210
acyclovir
Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.		1.97102-aminopurines;
oxopurine		antimetabolite;
antiviral drug
ganciclovir
[no description available]		1.97102-aminopurines;
oxopurine		antiinfective agent;
antiviral drug
7-deazainosine
[no description available]		1.9710
ConditionIndicatedRelationship StrengthStudiesTrials
Cytomegalovirus
A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.		01.9710
Absence Seizure
[description not available]		0210
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		0210