Page last updated: 2024-09-25

ah 6809

Description

6-isopropoxy-9-oxoxanthene-2-carboxylic acid: structure given in UD [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID119461
CHEMBL ID1317823
CHEBI ID95289
SCHEMBL ID1163801
MeSH IDM0152428

Synonyms (44)

Synonym
6-isopropoxy-9-oxo-9h-xanthene-2-carboxylic acid
HMS3266H17
BRD-K59339270-001-01-8
gtpl1896
tocris-0671
NCGC00024721-01
PDSP2_001532
PDSP1_001548
ah6809
6-(1-methylethoxy)-9-oxo-9h-xanthene-2-carboxylic acid
ah 6809
6-isopropoxy-9-oxoxanthene-2-carboxylic acid
9h-xanthene-2-carboxylic acid, 6-(1-methylethoxy)-9-oxo-
ah-6809
33458-93-4
L000101
9-oxo-6-propan-2-yloxyxanthene-2-carboxylic acid
bdbm85184
cas_33458-93-4
nsc_119461
CS-1549
HY-10418
SCHEMBL1163801
6-isopropoxy-9-xanthone-2-carboxylic acid
AQFFXPQJLZFABJ-UHFFFAOYSA-N
AKOS024458601
CHEMBL1317823
HMS3648F13
ah6809, >=98%, crystalline solid or supercooled liquid
DTXSID80187106
sr-01000597664
SR-01000597664-1
CHEBI:95289
J-019193
HMS3675O12
Q27074359
SR-01000597664-2
HMS3411O12
EX-A7711
A913344
BS-52004
6-isopropoxy-9-xanthone-2-carboxylicacid
9-oxo-6-(propan-2-yloxy)-9h-xanthene-2-carboxylic acid
E85579

Drug Classes (1)

ClassDescription
xanthonesAny member of the class of xanthenes based on a xanthone skeleton.
[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 (17)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency0.00080.004023.8416100.0000AID485290
Chain A, HADH2 proteinHomo sapiens (human)Potency15.84890.025120.237639.8107AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency15.84890.025120.237639.8107AID893
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency28.18380.177814.390939.8107AID2147
USP1 protein, partialHomo sapiens (human)Potency39.81070.031637.5844354.8130AID504865
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency39.81070.011212.4002100.0000AID1030
cellular tumor antigen p53 isoform aHomo sapiens (human)Potency15.84890.316212.443531.6228AID902
cytochrome P450 2C9 precursorHomo sapiens (human)Potency31.62280.00636.904339.8107AID883
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency39.81070.001815.663839.8107AID894
lethal factor (plasmid)Bacillus anthracis str. A2012Potency12.58930.020010.786931.6228AID912
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency31.62280.00638.235039.8107AID883
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin E2 receptor EP1 subtypeHomo sapiens (human)Ki1.20000.00910.66351.5849AID1151378
Prostaglandin E2 receptor EP4 subtypeHomo sapiens (human)Ki100.00000.00010.47443.1623AID1151380
Prostaglandin E2 receptor EP3 subtypeHomo sapiens (human)Ki1.60000.00031.70816.8000AID1151379
Prostaglandin E2 receptor EP2 subtypeHomo sapiens (human)Ki1.15000.00100.54483.0000AID1151377; AID1151383
Prostacyclin receptorHomo sapiens (human)Ki100.00000.00320.49586.6280AID1151382
Prostaglandin D2 receptorHomo sapiens (human)Ki1.40000.00060.49131.4000AID1151381
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (40)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
adenylate cyclase-activating dopamine receptor signaling pathwayProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
response to lipopolysaccharideProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
inflammatory responseProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
negative regulation of cytokine productionProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
positive regulation of cytokine productionProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
immune responseProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
JNK cascadeProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
response to mechanical stimulusProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
response to nematodeProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
regulation of ossificationProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
response to lipopolysaccharideProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
negative regulation of integrin activationProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
T-helper cell differentiationProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
negative regulation of inflammatory responseProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
positive regulation of inflammatory responseProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
regulation of stress fiber assemblyProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
bone developmentProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
ERK1 and ERK2 cascadeProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
cellular response to mechanical stimulusProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
negative regulation of eosinophil extravasationProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
cellular response to prostaglandin E stimulusProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
inflammatory responseProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
cell deathProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
positive regulation of fever generationProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
intestine smooth muscle contractionProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
inflammatory responseProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
negative regulation of gastric acid secretionProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
response to nematodeProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
response to lipopolysaccharideProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
response to progesteroneProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
regulation of cell population proliferationProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
cellular response to prostaglandin E stimulusProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
inflammatory responseProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerProstacyclin receptorHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstacyclin receptorHomo sapiens (human)
cell-cell signalingProstacyclin receptorHomo sapiens (human)
negative regulation of platelet-derived growth factor receptor signaling pathwayProstacyclin receptorHomo sapiens (human)
response to lipopolysaccharideProstacyclin receptorHomo sapiens (human)
negative regulation of smooth muscle cell proliferationProstacyclin receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstacyclin receptorHomo sapiens (human)
inflammatory responseProstacyclin receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayProstaglandin D2 receptorHomo sapiens (human)
male sex determinationProstaglandin D2 receptorHomo sapiens (human)
sleepProstaglandin D2 receptorHomo sapiens (human)
mast cell degranulationProstaglandin D2 receptorHomo sapiens (human)
adenosine metabolic processProstaglandin D2 receptorHomo sapiens (human)
cellular response to prostaglandin D stimulusProstaglandin D2 receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin D2 receptorHomo sapiens (human)
inflammatory responseProstaglandin D2 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
D1 dopamine receptor bindingProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
prostaglandin E receptor activityProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
prostaglandin E receptor activityProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
protein bindingProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
prostaglandin E receptor activityProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
prostaglandin E receptor activityProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
guanyl-nucleotide exchange factor activityProstacyclin receptorHomo sapiens (human)
prostacyclin receptor activityProstacyclin receptorHomo sapiens (human)
prostaglandin J receptor activityProstaglandin D2 receptorHomo sapiens (human)
prostaglandin D receptor activityProstaglandin D2 receptorHomo sapiens (human)
protein bindingProstaglandin D2 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
membraneProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
nuclear envelopeProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
membraneProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
cytosolProstacyclin receptorHomo sapiens (human)
plasma membraneProstacyclin receptorHomo sapiens (human)
plasma membraneProstacyclin receptorHomo sapiens (human)
plasma membraneProstaglandin D2 receptorHomo sapiens (human)
membraneProstaglandin D2 receptorHomo sapiens (human)
plasma membraneProstaglandin D2 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1151377Antagonist activity at EP2 receptor (unknown origin) by functional cAMP assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151378Antagonist activity at EP1 receptor (unknown origin) by functional cAMP assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151380Antagonist activity at EP4 receptor (unknown origin) by functional cAMP assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151382Antagonist activity at prostanoid IP receptor (unknown origin) by functional cAMP assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151379Antagonist activity at EP3 receptor (unknown origin) by functional cAMP assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151383Inhibition of EP2 receptor (unknown origin) by competitive binding assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151381Antagonist activity at DP1 receptor (unknown origin) by functional cAMP assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1346343Human EP3 receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346377Human DP1 receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346408Human EP1 receptor (Prostanoid receptors)2002The Journal of pharmacy and pharmacology, Apr, Volume: 54, Issue:4
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.
AID1346303Mouse EP2 receptor (Prostanoid receptors)1997British journal of pharmacology, Sep, Volume: 122, Issue:2
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
AID1346308Human EP2 receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346345Rat EP1 receptor (Prostanoid receptors)1997European journal of pharmacology, Dec-11, Volume: 340, Issue:2-3
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.
AID1346318Rat EP2 receptor (Prostanoid receptors)1997European journal of pharmacology, Dec-11, Volume: 340, Issue:2-3
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.
AID1346408Human EP1 receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (159)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (1.89)18.7374
1990's39 (24.53)18.2507
2000's62 (38.99)29.6817
2010's50 (31.45)24.3611
2020's5 (3.14)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 (0.61%)5.53%
Reviews2 (1.23%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other160 (98.16%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Long-term Use (2)

ArticleYear
EP4 receptor as a new target for bronchodilator therapy.
Thorax, Volume: 66, Issue: 12
2011
Prostaglandin E2 mediates cough via the EP3 receptor: implications for future disease therapy.
American journal of respiratory and critical care medicine, Nov-15, Volume: 180, Issue: 10
2009
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (4)

ArticleYear
Thromboxane and isoprostane share the same prostanoid receptors to increase human placental tone.
Placenta, Volume: 32, Issue: 12
2011
Role of PGE(2) in protease-activated receptor-1, -2 and -4 mediated relaxation in the mouse isolated trachea.
British journal of pharmacology, Volume: 132, Issue: 1
2001
Blockade by ONO-NT-012, a unique prostanoid analogue, of prostaglandin E2-induced allodynia in conscious mice.
British journal of pharmacology, Volume: 115, Issue: 1
1995
Evaluation of ZK110841 and AH6809, an agonist and an antagonist of prostaglandin DP-receptors on human platelets, with a PGD2-responsive cell line from bovine embryonic trachea.
British journal of pharmacology, Volume: 99, Issue: 1
1990
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]