Page last updated: 2024-11-11

n-((1s,trans)-2-hydroxycyclopentyl)adenosine

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

Description

N-((1S,trans)-2-hydroxycyclopentyl)adenosine: structure given in first source; an adenosine A1 receptor agonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9884817
CHEMBL ID2163568
CHEBI ID92714
SCHEMBL ID2779184
MeSH IDM0219334

Synonyms (37)

Synonym
124555-18-6
HMS3268O08
BRD-K40578143-001-01-8
gr79236
gr-79236
n-((1s,2s)-2-hydroxycyclopentyl)adenosine
gr 79236x
n-((1s,trans)-2-hydroxycyclopentyl)adenosine
adenosine, n-(2-hydroxycyclopentyl)-, (1s-trans)-
bdbm50395126
CHEMBL2163568 ,
q4h682b2vz ,
unii-q4h682b2vz
n-[(1s,2s)-2-hydroxycyclopentyl adenosine
(2r,3r,4s,5r)-2-(6-{[(1s,2s)-2-hydroxycyclopentyl]amino}-9h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
gtpl3288
HY-18978
CS-4965
SCHEMBL2779184
GYWXTRVEUURNEW-TVDBPQCTSA-N
n-[(1s,trans)-2-hydroxycyclopentyl]adenosine
adenosine, n-((1s,2s)-2-hydroxycyclopentyl)-
n-[(1s,2s)-2-hydroxycyclopentyl]adenosine
AKOS024456878
DTXSID10154427
n-[(1s,2s)-2-hydroxy-cyclopentyl]-adenosne
J-523291
CHEBI:92714
gr 79236x, >=99% (hplc), solid
gr79236x
HMS3676N18
Q27077849
HMS3412N18
(2r,3r,4s,5r)-2-[6-[[(1s,2s)-2-hydroxycyclopentyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
MS-25429
ZEA55518
adenosine, n-[(1s,2s)-2-hydroxycyclopentyl]-

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Blood pressure and heart rate were continuously recorded in rats for 30 min before and 1 h after oral dosing with GR79236 (0."( The effects of GR79236 on plasma fatty acid concentrations, heart rate and blood pressure in the conscious rat.
Coates, J; Gardner, CJ; Strong, P; Twissell, DJ, 1994
)
0.29
"The dose-response effects of a new adenosine agonist, GR79236, were examined in isolated rat soleus muscle strips and human rectus abdominus muscle strips."( In vitro effect of adenosine agonist GR79236 on the insulin sensitivity of glucose utilisation in rat soleus and human rectus abdominus muscle.
Heseltine, L; Taylor, R; Webster, JM, 1996
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
purine nucleoside
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
Purinergic signaling053

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki0.00310.00011.20929.9700AID1571131
Adenosine receptor A2aHomo sapiens (human)Ki1.33000.00001.06099.7920AID1571134
Adenosine receptor A1Homo sapiens (human)Ki0.00390.00020.931610.0000AID1571129
[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)
Adenosine receptor A1Homo sapiens (human)EC50 (µMol)0.00590.00010.99169.8000AID699043
Cannabinoid receptor 2Rattus norvegicus (Norway rat)EC50 (µMol)0.00590.00030.06660.3150AID699043
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (91)

Processvia Protein(s)Taxonomy
synaptic transmission, dopaminergicAdenosine receptor A2aHomo sapiens (human)
response to amphetamineAdenosine receptor A2aHomo sapiens (human)
regulation of DNA-templated transcriptionAdenosine receptor A2aHomo sapiens (human)
phagocytosisAdenosine receptor A2aHomo sapiens (human)
apoptotic processAdenosine receptor A2aHomo sapiens (human)
inflammatory responseAdenosine receptor A2aHomo sapiens (human)
cellular defense responseAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
cell-cell signalingAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, cholinergicAdenosine receptor A2aHomo sapiens (human)
central nervous system developmentAdenosine receptor A2aHomo sapiens (human)
blood coagulationAdenosine receptor A2aHomo sapiens (human)
sensory perceptionAdenosine receptor A2aHomo sapiens (human)
locomotory behaviorAdenosine receptor A2aHomo sapiens (human)
blood circulationAdenosine receptor A2aHomo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A2aHomo sapiens (human)
response to xenobiotic stimulusAdenosine receptor A2aHomo sapiens (human)
response to inorganic substanceAdenosine receptor A2aHomo sapiens (human)
positive regulation of glutamate secretionAdenosine receptor A2aHomo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmissionAdenosine receptor A2aHomo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A2aHomo sapiens (human)
response to purine-containing compoundAdenosine receptor A2aHomo sapiens (human)
response to caffeineAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
positive regulation of urine volumeAdenosine receptor A2aHomo sapiens (human)
vasodilationAdenosine receptor A2aHomo sapiens (human)
eating behaviorAdenosine receptor A2aHomo sapiens (human)
negative regulation of vascular permeabilityAdenosine receptor A2aHomo sapiens (human)
negative regulation of neuron apoptotic processAdenosine receptor A2aHomo sapiens (human)
positive regulation of circadian sleep/wake cycle, sleepAdenosine receptor A2aHomo sapiens (human)
negative regulation of alpha-beta T cell activationAdenosine receptor A2aHomo sapiens (human)
astrocyte activationAdenosine receptor A2aHomo sapiens (human)
neuron projection morphogenesisAdenosine receptor A2aHomo sapiens (human)
positive regulation of protein secretionAdenosine receptor A2aHomo sapiens (human)
negative regulation of inflammatory responseAdenosine receptor A2aHomo sapiens (human)
regulation of mitochondrial membrane potentialAdenosine receptor A2aHomo sapiens (human)
membrane depolarizationAdenosine receptor A2aHomo sapiens (human)
regulation of calcium ion transportAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
inhibitory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
prepulse inhibitionAdenosine receptor A2aHomo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2aHomo sapiens (human)
positive regulation of long-term synaptic potentiationAdenosine receptor A2aHomo sapiens (human)
positive regulation of apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
temperature homeostasisAdenosine receptor A1Homo sapiens (human)
response to hypoxiaAdenosine receptor A1Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A1Homo sapiens (human)
regulation of respiratory gaseous exchange by nervous system processAdenosine receptor A1Homo sapiens (human)
negative regulation of acute inflammatory responseAdenosine receptor A1Homo sapiens (human)
negative regulation of leukocyte migrationAdenosine receptor A1Homo sapiens (human)
positive regulation of peptide secretionAdenosine receptor A1Homo sapiens (human)
positive regulation of systemic arterial blood pressureAdenosine receptor A1Homo sapiens (human)
negative regulation of systemic arterial blood pressureAdenosine receptor A1Homo sapiens (human)
regulation of glomerular filtrationAdenosine receptor A1Homo sapiens (human)
protein targeting to membraneAdenosine receptor A1Homo sapiens (human)
phagocytosisAdenosine receptor A1Homo sapiens (human)
inflammatory responseAdenosine receptor A1Homo sapiens (human)
signal transductionAdenosine receptor A1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayAdenosine receptor A1Homo sapiens (human)
cell-cell signalingAdenosine receptor A1Homo sapiens (human)
nervous system developmentAdenosine receptor A1Homo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A1Homo sapiens (human)
response to inorganic substanceAdenosine receptor A1Homo sapiens (human)
negative regulation of glutamate secretionAdenosine receptor A1Homo sapiens (human)
response to purine-containing compoundAdenosine receptor A1Homo sapiens (human)
lipid catabolic processAdenosine receptor A1Homo sapiens (human)
negative regulation of synaptic transmission, GABAergicAdenosine receptor A1Homo sapiens (human)
positive regulation of nucleoside transportAdenosine receptor A1Homo sapiens (human)
negative regulation of neurotrophin productionAdenosine receptor A1Homo sapiens (human)
positive regulation of protein dephosphorylationAdenosine receptor A1Homo sapiens (human)
vasodilationAdenosine receptor A1Homo sapiens (human)
negative regulation of circadian sleep/wake cycle, non-REM sleepAdenosine receptor A1Homo sapiens (human)
negative regulation of apoptotic processAdenosine receptor A1Homo sapiens (human)
positive regulation of potassium ion transportAdenosine receptor A1Homo sapiens (human)
positive regulation of MAPK cascadeAdenosine receptor A1Homo sapiens (human)
negative regulation of hormone secretionAdenosine receptor A1Homo sapiens (human)
cognitionAdenosine receptor A1Homo sapiens (human)
leukocyte migrationAdenosine receptor A1Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of painAdenosine receptor A1Homo sapiens (human)
negative regulation of lipid catabolic processAdenosine receptor A1Homo sapiens (human)
positive regulation of lipid catabolic processAdenosine receptor A1Homo sapiens (human)
regulation of sensory perception of painAdenosine receptor A1Homo sapiens (human)
negative regulation of synaptic transmission, glutamatergicAdenosine receptor A1Homo sapiens (human)
fatty acid homeostasisAdenosine receptor A1Homo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A1Homo sapiens (human)
long-term synaptic depressionAdenosine receptor A1Homo sapiens (human)
mucus secretionAdenosine receptor A1Homo sapiens (human)
negative regulation of mucus secretionAdenosine receptor A1Homo sapiens (human)
triglyceride homeostasisAdenosine receptor A1Homo sapiens (human)
regulation of cardiac muscle cell contractionAdenosine receptor A1Homo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A1Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentrationAdenosine receptor A1Homo sapiens (human)
negative regulation of long-term synaptic potentiationAdenosine receptor A1Homo sapiens (human)
negative regulation of long-term synaptic depressionAdenosine receptor A1Homo sapiens (human)
G protein-coupled receptor signaling pathwayAdenosine receptor A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A2aHomo sapiens (human)
protein bindingAdenosine receptor A2aHomo sapiens (human)
calmodulin bindingAdenosine receptor A2aHomo sapiens (human)
lipid bindingAdenosine receptor A2aHomo sapiens (human)
enzyme bindingAdenosine receptor A2aHomo sapiens (human)
type 5 metabotropic glutamate receptor bindingAdenosine receptor A2aHomo sapiens (human)
identical protein bindingAdenosine receptor A2aHomo sapiens (human)
protein-containing complex bindingAdenosine receptor A2aHomo sapiens (human)
alpha-actinin bindingAdenosine receptor A2aHomo sapiens (human)
G protein-coupled receptor bindingAdenosine receptor A1Homo sapiens (human)
purine nucleoside bindingAdenosine receptor A1Homo sapiens (human)
protein bindingAdenosine receptor A1Homo sapiens (human)
heat shock protein bindingAdenosine receptor A1Homo sapiens (human)
G-protein beta/gamma-subunit complex bindingAdenosine receptor A1Homo sapiens (human)
heterotrimeric G-protein bindingAdenosine receptor A1Homo sapiens (human)
protein heterodimerization activityAdenosine receptor A1Homo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A2aHomo sapiens (human)
intermediate filamentAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2aHomo sapiens (human)
membraneAdenosine receptor A2aHomo sapiens (human)
dendriteAdenosine receptor A2aHomo sapiens (human)
axolemmaAdenosine receptor A2aHomo sapiens (human)
asymmetric synapseAdenosine receptor A2aHomo sapiens (human)
presynaptic membraneAdenosine receptor A2aHomo sapiens (human)
neuronal cell bodyAdenosine receptor A2aHomo sapiens (human)
postsynaptic membraneAdenosine receptor A2aHomo sapiens (human)
presynaptic active zoneAdenosine receptor A2aHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A1Homo sapiens (human)
plasma membraneAdenosine receptor A1Homo sapiens (human)
basolateral plasma membraneAdenosine receptor A1Homo sapiens (human)
axolemmaAdenosine receptor A1Homo sapiens (human)
asymmetric synapseAdenosine receptor A1Homo sapiens (human)
presynaptic membraneAdenosine receptor A1Homo sapiens (human)
neuronal cell bodyAdenosine receptor A1Homo sapiens (human)
terminal boutonAdenosine receptor A1Homo sapiens (human)
dendritic spineAdenosine receptor A1Homo sapiens (human)
calyx of HeldAdenosine receptor A1Homo sapiens (human)
postsynaptic membraneAdenosine receptor A1Homo sapiens (human)
presynaptic active zoneAdenosine receptor A1Homo sapiens (human)
synapseAdenosine receptor A1Homo sapiens (human)
dendriteAdenosine receptor A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1571138Displacement of [125I]I-AB-MECA from recombinant human adenosine A3 receptor expressed in CHO cell membranes2018MedChemComm, Nov-01, Volume: 9, Issue:11
Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A
AID1571134Displacement of [3H]ZM241385 from human A2A receptor expressed in HEK293 cell membranes2018MedChemComm, Nov-01, Volume: 9, Issue:11
Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A
AID1571129Displacement of [3H]DPCPX from recombinant human A1 receptor expressed in CHO cell membranes2018MedChemComm, Nov-01, Volume: 9, Issue:11
Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A
AID1571131Displacement of [3H]DPCPX from rat A1 receptor2018MedChemComm, Nov-01, Volume: 9, Issue:11
Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A
AID699043Agonist activity at human A1AR expressed in HEK293T/17 cells assessed as inhibition of forskolin-induced cAMP accumulation incubated for 10 mins by luciferase reporter assay2012Journal of medicinal chemistry, Jul-26, Volume: 55, Issue:14
Orally active adenosine A(1) receptor agonists with antinociceptive effects in mice.
AID1345630Rat A1 receptor (Adenosine receptors)2006Nature reviews. Drug discovery, Mar, Volume: 5, Issue:3
Adenosine receptors as therapeutic targets.
AID1345618Human A2A receptor (Adenosine receptors)2006Nature reviews. Drug discovery, Mar, Volume: 5, Issue:3
Adenosine receptors as therapeutic targets.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's15 (51.72)18.2507
2000's12 (41.38)29.6817
2010's2 (6.90)24.3611
2020's0 (0.00)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 (%)
Trials4 (13.79%)5.53%
Reviews1 (3.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (82.76%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]