Page last updated: 2024-11-12

arl-67156

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

Description

6-N,N-diethyl-beta,gamma-dibromomethylene-D-ATP: an inhibitor of ecto-ATPase [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10078572
CHEMBL ID1206141
MeSH IDM0243980

Synonyms (19)

Synonym
CHEMBL1206141 ,
LOPAC0_000149
fpl 67156
5'-o-[(r)-{[(r)-[dibromo(phosphono)methyl](hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-n,n-diethyladenosine
ARU ,
arl-67156
160928-38-1
fpl-67156
arl 67156
6-n,n-diethyl-beta,gamma-dibromomethylene-d-atp
[dibromo-[[[(2r,3s,4r,5r)-5-(6-diethylaminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]methyl]phosphonic acid
gtpl9030
bdbm50179358
6-n,n-diethyl-d-beta-gamma-dibromomethylene atp
[dibromo-[[[(2r,3s,4r,5r)-5-[6-(diethylamino)purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]methyl]phosphonic acid
Q27074508
DTXSID301017960
5'-adenylicacid,n,n-diethyl-,5'-anhydridewithp,p'-(dibromomethylene)bis[phosphonicacid]
5'-adenylic acid, n,n-diethyl-, 5'-anhydride with p,p'-(dibromomethylene)bis[phosphonic acid]

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The best investigated NPP1 inhibitors so far are nucleotide derivatives and analogs, however they are not orally bioavailable due to their high polarity."( Thiazolo[3,2-a]benzimidazol-3(2H)-one derivatives: Structure-activity relationships of selective nucleotide pyrophosphatase/phosphodiesterase1 (NPP1) inhibitors.
De Jonghe, S; Hanck, T; Herdewijn, P; Lee, SY; Müller, CE; Perotti, A, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)Ki12.00000.52003.93508.1900AID1306447; AID1415788; AID1692615
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (31)

Processvia Protein(s)Taxonomy
nucleoside triphosphate catabolic processEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
nucleoside diphosphate catabolic processEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
generation of precursor metabolites and energyEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
phosphate-containing compound metabolic processEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
immune responseEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
nucleoside triphosphate catabolic processEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
response to inorganic substanceEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
gene expressionEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
vesicle-mediated transportEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
bone mineralizationEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
negative regulation of cell growthEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
melanocyte differentiationEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
regulation of bone mineralizationEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
negative regulation of bone mineralizationEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
inorganic diphosphate transportEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
intracellular phosphate ion homeostasisEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
sequestering of triglycerideEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
negative regulation of protein autophosphorylationEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
cellular response to insulin stimulusEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
response to ATPEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
negative regulation of fat cell differentiationEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
negative regulation of glycogen biosynthetic processEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
ATP metabolic processEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
negative regulation of glucose importEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
3'-phosphoadenosine 5'-phosphosulfate metabolic processEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
phosphate ion homeostasisEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
nucleic acid metabolic processEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
negative regulation of hh target transcription factor activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
cell adhesionEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
blood coagulationEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
platelet aggregationEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
nucleoside diphosphate catabolic processEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (32)

Processvia Protein(s)Taxonomy
apyrase activityEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
protein bindingEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
ATP bindingEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
nucleoside diphosphate phosphatase activityEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
ribonucleoside triphosphate phosphatase activityEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
GDP phosphatase activityEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
UDP phosphatase activityEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
nucleic acid bindingEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
exonuclease activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
phosphodiesterase I activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
dinucleotide phosphatase activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
scavenger receptor activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
insulin receptor bindingEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
calcium ion bindingEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
protein bindingEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
ATP bindingEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
zinc ion bindingEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
phosphatase activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
polysaccharide bindingEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
GTP diphosphatase activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
UTP diphosphatase activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
protein homodimerization activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
nucleoside triphosphate diphosphatase activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
ATP diphosphatase activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
3'-phosphoadenosine 5'-phosphosulfate bindingEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
cyclic-GMP-AMP hydrolase activityEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
GTPase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
apyrase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
protein bindingEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
ATP bindingEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
ATP hydrolysis activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
nucleoside diphosphate phosphatase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
ribonucleoside triphosphate phosphatase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
CDP phosphatase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
ADP phosphatase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
CTPase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
ITPase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
IDP phosphatase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
UDP phosphatase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
GDP phosphatase activityEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membraneEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
plasma membraneEctonucleoside triphosphate diphosphohydrolase 3Homo sapiens (human)
plasma membraneEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
extracellular spaceEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
lysosomal membraneEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
plasma membraneEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
cell surfaceEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
membraneEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
basolateral plasma membraneEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
cell surfaceEctonucleotide pyrophosphatase/phosphodiesterase family member 1Homo sapiens (human)
plasma membraneEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
caveolaEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
membraneEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
extracellular exosomeEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
plasma membraneEctonucleoside triphosphate diphosphohydrolase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1415788Competitive-inhibition of recombinant human NPP1 expressed in HEK293 cell membranes using p-Nph-5'-TMP as substrate pretreated for 3 mins followed by substrate addition and measured after 15 mins by HPLC method2017MedChemComm, May-01, Volume: 8, Issue:5
Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) and its inhibitors.
AID1692610Competitive inhibition of human CD39 using ATP as substrate preincubated for 3 mins followed by substrate addition and measured after 15 mins by Dixon and Cornish-Bowden plot analysis2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Targeting Metabolism of Extracellular Nucleotides via Inhibition of Ectonucleotidases CD73 and CD39.
AID1692615Competitive inhibition of human NPP1 using pnp-TMP as substrate preincubated for 3 mins followed by substrate addition and measured after 15 mins by Dixon and Cornish-Bowden plot analysis2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Targeting Metabolism of Extracellular Nucleotides via Inhibition of Ectonucleotidases CD73 and CD39.
AID1692614Competitive inhibition of human NTPDase3 using ATP as substrate preincubated for 3 mins followed by substrate addition and measured after 15 mins by Dixon and Cornish-Bowden plot analysis2020Journal of medicinal chemistry, 11-25, Volume: 63, Issue:22
Targeting Metabolism of Extracellular Nucleotides via Inhibition of Ectonucleotidases CD73 and CD39.
AID1306447Competitive inhibition of human NPP1 transfected in HEK293 cells using p-Nph-5'-TMP as substrate preincubated for 3 mins followed by substrate addition measured after 15 mins by Cornish-Bowden plot analysis2016Bioorganic & medicinal chemistry, 07-15, Volume: 24, Issue:14
Thiazolo[3,2-a]benzimidazol-3(2H)-one derivatives: Structure-activity relationships of selective nucleotide pyrophosphatase/phosphodiesterase1 (NPP1) inhibitors.
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.
AID1346286Rat ectonucleoside triphosphate diphosphohydrolase 1 (Hydrolases)2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Selective nucleoside triphosphate diphosphohydrolase-2 (NTPDase2) inhibitors: nucleotide mimetics derived from uridine-5'-carboxamide.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (75)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's9 (12.00)18.2507
2000's36 (48.00)29.6817
2010's29 (38.67)24.3611
2020's1 (1.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.23

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index22.23 (24.57)
Research Supply Index4.33 (2.92)
Research Growth Index4.71 (4.65)
Search Engine Demand Index23.70 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.23)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (4.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other72 (96.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]