Page last updated: 2024-11-11

4-oxo-6-((pyrimidin-2-ylthio)methyl)-4h-pyran-3-yl 4-nitrobenzoate

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Description

4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID7217941
CHEMBL ID2158347
CHEBI ID92965
SCHEMBL ID17326564
MeSH IDM0582163

Synonyms (34)

Synonym
MLS-0437359.0001
ml221
MLS-0437359.0002
AB00687545-01
[4-oxo-6-(pyrimidin-2-ylsulfanylmethyl)pyran-3-yl] 4-nitrobenzoate
MLS003389520
smr002078184
chembl2158347 ,
bdbm50393964
4-oxo-6-((pyrimidin-2-ylthio)methyl)-4h-pyran-3-yl 4-nitrobenzoate
F2510-0124
877636-42-5
S8695
gtpl6282
AKOS016372065
SCHEMBL17326564
5-[(4-nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4h-pyran-4-one
ml 221
sr-01000020403
SR-01000020403-1
CHEBI:92965
HY-103254
CS-0026651
ml-221
BCP28945
Q27087039
AS-16633
EX-A2798
SB19613
HMS3749G21
CCG-268469
C76891
CKB63642
AC-36271
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
nitrobenzoic acidAny member of the class of benzoic acids with at least one nitro substituent attached to the benzene ring.
[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]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
type-1 angiotensin II receptorHomo sapiens (human)IC50 (µMol)79.00002.22108.230418.7980AID488810; AID492984
apelin receptorHomo sapiens (human)IC50 (µMol)1.95501.75003.39008.3500AID488803; AID492986
Type-1 angiotensin II receptorHomo sapiens (human)IC50 (µMol)79.00000.00020.09323.6000AID695141
Apelin receptorHomo sapiens (human)IC50 (µMol)1.22500.00120.81711.7500AID695140; AID695142
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (51)

Processvia Protein(s)Taxonomy
regulation of cell growthType-1 angiotensin II receptorHomo sapiens (human)
kidney developmentType-1 angiotensin II receptorHomo sapiens (human)
renin-angiotensin regulation of aldosterone productionType-1 angiotensin II receptorHomo sapiens (human)
maintenance of blood vessel diameter homeostasis by renin-angiotensinType-1 angiotensin II receptorHomo sapiens (human)
regulation of systemic arterial blood pressure by renin-angiotensinType-1 angiotensin II receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayType-1 angiotensin II receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationType-1 angiotensin II receptorHomo sapiens (human)
Rho protein signal transductionType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationType-1 angiotensin II receptorHomo sapiens (human)
regulation of vasoconstrictionType-1 angiotensin II receptorHomo sapiens (human)
calcium-mediated signalingType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of phospholipase A2 activityType-1 angiotensin II receptorHomo sapiens (human)
low-density lipoprotein particle remodelingType-1 angiotensin II receptorHomo sapiens (human)
regulation of renal sodium excretionType-1 angiotensin II receptorHomo sapiens (human)
angiotensin-activated signaling pathwayType-1 angiotensin II receptorHomo sapiens (human)
regulation of cell population proliferationType-1 angiotensin II receptorHomo sapiens (human)
symbiont entry into host cellType-1 angiotensin II receptorHomo sapiens (human)
regulation of inflammatory responseType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of inflammatory responseType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of protein metabolic processType-1 angiotensin II receptorHomo sapiens (human)
cell chemotaxisType-1 angiotensin II receptorHomo sapiens (human)
phospholipase C-activating angiotensin-activated signaling pathwayType-1 angiotensin II receptorHomo sapiens (human)
blood vessel diameter maintenanceType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of blood vessel endothelial cell proliferation involved in sprouting angiogenesisType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of CoA-transferase activityType-1 angiotensin II receptorHomo sapiens (human)
positive regulation of reactive oxygen species metabolic processType-1 angiotensin II receptorHomo sapiens (human)
inflammatory responseType-1 angiotensin II receptorHomo sapiens (human)
negative regulation of gene expressionApelin receptorHomo sapiens (human)
regulation of gap junction assemblyApelin receptorHomo sapiens (human)
angiogenesisApelin receptorHomo sapiens (human)
vasculogenesisApelin receptorHomo sapiens (human)
vasculature developmentApelin receptorHomo sapiens (human)
heart loopingApelin receptorHomo sapiens (human)
atrioventricular valve developmentApelin receptorHomo sapiens (human)
endocardial cushion formationApelin receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayApelin receptorHomo sapiens (human)
gastrulationApelin receptorHomo sapiens (human)
heart developmentApelin receptorHomo sapiens (human)
adult heart developmentApelin receptorHomo sapiens (human)
regulation of gene expressionApelin receptorHomo sapiens (human)
vascular associated smooth muscle cell differentiationApelin receptorHomo sapiens (human)
aorta developmentApelin receptorHomo sapiens (human)
negative regulation of cAMP-mediated signalingApelin receptorHomo sapiens (human)
positive regulation of angiogenesisApelin receptorHomo sapiens (human)
regulation of body fluid levelsApelin receptorHomo sapiens (human)
positive regulation of release of sequestered calcium ion into cytosolApelin receptorHomo sapiens (human)
ventricular septum morphogenesisApelin receptorHomo sapiens (human)
venous blood vessel developmentApelin receptorHomo sapiens (human)
coronary vasculature developmentApelin receptorHomo sapiens (human)
positive regulation of blood vessel endothelial cell proliferation involved in sprouting angiogenesisApelin receptorHomo sapiens (human)
positive regulation of inhibitory G protein-coupled receptor phosphorylationApelin receptorHomo sapiens (human)
blood vessel developmentApelin receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
angiotensin type I receptor activityType-1 angiotensin II receptorHomo sapiens (human)
angiotensin type II receptor activityType-1 angiotensin II receptorHomo sapiens (human)
protein bindingType-1 angiotensin II receptorHomo sapiens (human)
bradykinin receptor bindingType-1 angiotensin II receptorHomo sapiens (human)
protein heterodimerization activityType-1 angiotensin II receptorHomo sapiens (human)
G protein-coupled receptor activityApelin receptorHomo sapiens (human)
protein bindingApelin receptorHomo sapiens (human)
signaling receptor activityApelin receptorHomo sapiens (human)
apelin receptor activityApelin receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membraneType-1 angiotensin II receptorHomo sapiens (human)
membraneType-1 angiotensin II receptorHomo sapiens (human)
plasma membraneType-1 angiotensin II receptorHomo sapiens (human)
plasma membraneApelin receptorHomo sapiens (human)
plasma membraneApelin receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID695136Aqueous solubility of the compound at pH 7.42012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695139Selectivity ratio of IC50 for AT1 receptor to IC50 for APJ receptor (unknown receptor)2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695134Metabolic stability in mouse hepatic microsomes assessed as compound remaining at 60 mins2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695142Antagonist activity at APJ receptor expressed in CHOK1 cells assessed as inhibition of apelin13-induced beta-arrestin recruitment after 90 mins by luminescence assay2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695140Antagonist activity at APJ receptor assessed as inhibition of apelin13-induced cAMP accumulation2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695132Metabolic stability in plasma2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695141Inhibition of AT1 receptor2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695135Metabolic stability in human hepatic microsomes assessed as compound remaining at 60 mins2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695130Binding affinity to kappa-opioid receptor at 10 uM2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695138Permeability of the compound by PAMPA assay at pH 7.42012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695131Binding affinity to benzodiazepinone receptor at 10 uM2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695133Cytotoxicity against human hepatocytes2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID695137Plasma protein binding in mouse2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
AID1346467Human apelin receptor (Apelin receptor)2012Bioorganic & medicinal chemistry letters, Nov-01, Volume: 22, Issue:21
Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (46.15)24.3611
2020's7 (53.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.20

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 Index12.20 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.84 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.20)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]