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Ah 6809

CAS No.:
33458-93-4
Catalog Number:
AG00BXYZ
Molecular Formula:
C17H14O5
Molecular Weight:
298.2901
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$76
- +
5mg
≥98%
1 week
United States
$144
- +
10mg
99%
1 week
United States
$210
- +
50mg
99%
1 week
United States
$668
- +
100mg
99%
1 week
United States
$1140
- +
Product Description
Catalog Number:
AG00BXYZ
Chemical Name:
Ah 6809
CAS Number:
33458-93-4
Molecular Formula:
C17H14O5
Molecular Weight:
298.2901
MDL Number:
MFCD08056083
IUPAC Name:
9-oxo-6-propan-2-yloxyxanthene-2-carboxylic acid
InChI:
InChI=1S/C17H14O5/c1-9(2)21-11-4-5-12-15(8-11)22-14-6-3-10(17(19)20)7-13(14)16(12)18/h3-9H,1-2H3,(H,19,20)
InChI Key:
AQFFXPQJLZFABJ-UHFFFAOYSA-N
SMILES:
CC(Oc1ccc2c(c1)oc1c(c2=O)cc(cc1)C(=O)O)C
Properties
Complexity:
446  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
298.084g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
298.294g/mol
Monoisotopic Mass:
298.084g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
72.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.9  
Literature
Title Journal
Leptin induces CREB-dependent aromatase activation through COX-2 expression in breast cancer cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20170801
Role of hypoxia-inducible factor 1, α subunit and cAMP-response element binding protein 1 in synergistic release of interleukin 8 by prostaglandin E2 and nickel in lung fibroblasts. American journal of respiratory cell and molecular biology 20130701
Murine corneal stroma cells suppress bone marrow-derived dendritic cells maturation in vitro. Chinese medical journal 20120601
The cyclooxygenase-2 pathway via the PGE₂ EP2 receptor contributes to oligodendrocytes apoptosis in cuprizone-induced demyelination. Journal of neurochemistry 20120501
Prostaglandin E2 blocks menadione-induced apoptosis through the Ras/Raf/Erk signaling pathway in promonocytic leukemia cell lines. Molecules and cells 20120430
Prostaglandin E2 restrains macrophage maturation via E prostanoid receptor 2/protein kinase A signaling. Blood 20120308
Influence of influenza A infection on capsaicin-induced responses in murine airways. The Journal of pharmacology and experimental therapeutics 20120201
Prostaglandin E2 induces spontaneous rhythmic activity in mouse urinary bladder independently of efferent nerves. British journal of pharmacology 20120101
Acute effects of prostaglandin E1 and E2 on vascular reactivity and blood flow in situ in the chick chorioallantoic membrane. Prostaglandins, leukotrienes, and essential fatty acids 20120101
Primary human airway epithelial cell-dependent inhibition of human lung mast cell degranulation. PloS one 20120101
PGE(2)-induced CXCL12 production and CXCR4 expression controls the accumulation of human MDSCs in ovarian cancer environment. Cancer research 20111215
EP4 receptor as a new target for bronchodilator therapy. Thorax 20111201
SO(2)-induced neurotoxicity is mediated by cyclooxygenases-2-derived prostaglandin E(2) and its downstream signaling pathway in rat hippocampal neurons. Toxicological sciences : an official journal of the Society of Toxicology 20111201
Thromboxane and isoprostane share the same prostanoid receptors to increase human placental tone. Placenta 20111201
Thromboxane prostanoid receptor activation amplifies airway stretch-activated contractions assessed in perfused intact bovine bronchial segments. The Journal of pharmacology and experimental therapeutics 20111001
Suppressive effect of aqueous humor on lipopolysaccharide-induced dendritic cell maturation. Japanese journal of ophthalmology 20110901
Tumor-secreted PGE2 inhibits CCL5 production in activated macrophages through cAMP/PKA signaling pathway. The Journal of biological chemistry 20110121
Cyclooxygenase-2 up-regulates vascular endothelial growth factor via a protein kinase C pathway in non-small cell lung cancer. Journal of experimental & clinical cancer research : CR 20110101
Inhibitory influence of protease-activated receptor 2 and E-prostanoid receptor stimulants in lipopolysaccharide models of acute airway inflammation. The Journal of pharmacology and experimental therapeutics 20101101
The role of cyclooxygenase-2-dependent signaling via cyclic AMP response element activation on aromatase up-regulation by o,p'-DDT in human breast cancer cells. Toxicology letters 20101020
Jack bean urease alters serotonin-induced effects on Rhodnius prolixus anterior midgut. Journal of insect physiology 20100901
Functional and molecular characterization of prostaglandin E2 dilatory receptors in the rat craniovascular system in relevance to migraine. Cephalalgia : an international journal of headache 20100901
Inducible cyclooxygenase released prostaglandin E2 modulates the severity of infection caused by Streptococcus pyogenes. Journal of immunology (Baltimore, Md. : 1950) 20100815
Selective blockade of prostaglandin E2 receptors EP2 and EP4 signaling inhibits proliferation of human endometriotic epithelial cells and stromal cells through distinct cell cycle arrest. Fertility and sterility 20100515
Prostaglandin E2 induces CYP1B1 expression via ligand-independent activation of the ERalpha pathway in human breast cancer cells. Toxicological sciences : an official journal of the Society of Toxicology 20100401
Human papillomavirus type 16 E5 protein inhibits hydrogen-peroxide-induced apoptosis by stimulating ubiquitin-proteasome-mediated degradation of Bax in human cervical cancer cells. Carcinogenesis 20100301
Age-related changes in isoprostane-mediated relaxation of piglet blood vessels. Frontiers in bioscience (Elite edition) 20100101
Expression of cyclooxygenase-1/-2, microsomal prostaglandin-E synthase-1 and E-prostanoid receptor 2 and regulation of inflammatory mediators by PGE(2) in the amoeboid microglia in hypoxic postnatal rats and murine BV-2 cells. Neuroscience 20091215
Role of prostanoid production and receptors in the regulation of retinal endogenous amino acid neurotransmitters by 8-isoprostaglandin E2, ex vivo. Neurochemical research 20091201
Differential afferent sensitivity to mucosal lipopolysaccharide from Salmonella typhimurium and Escherichia coli in the rat jejunum. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20091201
Involvement of cyclooxygenase-2 in carbachol-induced positive inotropic response in mouse isolated left atrium. The Journal of pharmacology and experimental therapeutics 20091201
Prostaglandin E2 mediates cough via the EP3 receptor: implications for future disease therapy. American journal of respiratory and critical care medicine 20091115
Chronic methionine load-induced hyperhomocysteinemia impairs the relaxation induced by bradykinin in the isolated rat carotid. Amino acids 20091001
The EP1 subtype of prostaglandin E2 receptor: role in keratinocyte differentiation and expression in non-melanoma skin cancer. Prostaglandins, leukotrienes, and essential fatty acids 20091001
Regulation of ANP secretion from isolated atria by prostaglandins and cyclooxygenase-2. Peptides 20090901
Ketamine inhibits the phagocytic responses of canine peripheral blood polymorphonuclear cells through the upregulation of prostaglandin E2 in peripheral blood mononuclear cells in vitro. Research in veterinary science 20090801
Activation of prostaglandin E2 EP1 receptor increases arteriolar tone and blood pressure in mice with type 2 diabetes. Cardiovascular research 20090701
Prostaglandin E2 released from activated microglia enhances astrocyte proliferation in vitro. Toxicology and applied pharmacology 20090701
Prostaglandin E2 signaling through E prostanoid receptor 2 impairs proliferative response of double negative regulatory T cells. International immunopharmacology 20090501
Developmental changes in the effects of prostaglandin E2 in the chicken ductus arteriosus. Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20090201
Prostaglandin E2 and its cognate EP receptors control human adult articular cartilage homeostasis and are linked to the pathophysiology of osteoarthritis. Arthritis and rheumatism 20090201
Effect of prostaglandin E2 on urokinase-type plasminogen activator production by human lung fibroblasts. Scandinavian journal of clinical and laboratory investigation 20090101
Roles of cyclooxygenase-2 in microvascular endothelial cell proliferation induced by basic fibroblast growth factor. Chinese medical journal 20081220
15d-PGJ2 upregulates synthesis of IL-8 in endothelial cells through induction of oxidative stress. Antioxidants & redox signaling 20081201
Engagement of the EP2 prostanoid receptor closes the K+ channel KCa3.1 in human lung mast cells and attenuates their migration. European journal of immunology 20080901
The effects of cyclooxygenase2-prostaglandinE2 pathway on Helicobacter pylori-induced urokinase-type plasminogen activator system in the gastric cancer cells. Helicobacter 20080601
The role of prostaglandin E and thromboxane-prostanoid receptors in the response to prostaglandin E2 in the aorta of Wistar Kyoto rats and spontaneously hypertensive rats. Cardiovascular research 20080401
Prostaglandin E2 glycerol ester, an endogenous COX-2 metabolite of 2-arachidonoylglycerol, induces hyperalgesia and modulates NFkappaB activity. British journal of pharmacology 20080401
Prostaglandin E2 and F2alpha activate the FP receptor and up-regulate cyclooxygenase-2 expression via the cyclic AMP response element. Molecular and cellular endocrinology 20080326
PTGER1 and PTGER2 receptors mediate regulation of progesterone synthesis and type 1 11beta-hydroxysteroid dehydrogenase activity by prostaglandin E2 in human granulosa lutein cells. The Journal of endocrinology 20070901
Prostaglandin E2 enhances acetylcholine-induced, Ca2+-dependent ionic currents in swine tracheal mucous gland cells. The Journal of pharmacology and experimental therapeutics 20070801
Prostaglandin E2 enhances the sensitizing effect of hyperthermia on pulmonary C-fibers in rats. Respiratory physiology & neurobiology 20070615
Development and validation of a liquid chromatography/tandem mass spectrometry method for the determination of DMXAA in human and mouse plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070601
TNF-alpha modulates hepatic Na+-K+ ATPase activity via PGE2 and EP2 receptors. Prostaglandins & other lipid mediators 20070601
Functional characterization of the mechanisms underlying bradykinin-induced relaxation in the isolated rat carotid artery. Life sciences 20070417
Iloprost-induced desensitization of the prostacyclin receptor in isolated rabbit lungs. Respiratory research 20070101
Involvement of cyclooxygenase-2--prostaglandin E2 pathway in interleukin-8 production in gastric cancer cells. Digestive diseases and sciences 20061201
Prostaglandin E2 promotes cell survival of glomerular epithelial cells via the EP4 receptor. American journal of physiology. Renal physiology 20060601
Identification of prostaglandin E2 receptor subtype 2 as a receptor activated by OxPAPC. Circulation research 20060317
Early changes in prostaglandins precede bone formation in a rabbit model of heterotopic ossification. Bone 20060301
Involvement of EP1 and EP2 receptors in the regulation of the Na,K-ATPase by prostaglandins in MDCK cells. Prostaglandins & other lipid mediators 20060301
Role of periaqueductal grey prostaglandin receptors in formalin-induced hyperalgesia. European journal of pharmacology 20060113
Prostaglandin E2 drives cyclooxygenase-2 expression via cyclic AMP response element activation in human pancreatic cancer cells. Cancer biology & therapy 20051101
Lipopolysaccharide-induced changes in mesenteric afferent sensitivity of rat jejunum in vitro: role of prostaglandins. American journal of physiology. Gastrointestinal and liver physiology 20050801
Sensitization of mesenteric afferents to chemical and mechanical stimuli following systemic bacterial lipopolysaccharide. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20050201
EP1- and EP3-receptors mediate prostaglandin E2-induced constriction of porcine large cerebral arteries. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20041201
Implication of prostaglandin E(2) in TNF-alpha-induced release of m-calpain from HCS-2/8 chondrocytes. Inhibition of m-calpain release by NSAIDs. Osteoarthritis and cartilage 20041101
Prostacyclin release and receptor activation: differential control of human pulmonary venous and arterial tone. British journal of pharmacology 20040601
Prostaglandin E2 regulates amyloid precursor protein expression via the EP2 receptor in cultured rat microglia. Neuroscience letters 20040520
Identification in human airways smooth muscle cells of the prostanoid receptor and signalling pathway through which PGE2 inhibits the release of GM-CSF. British journal of pharmacology 20040401
E-ring 8-isoprostanes inhibit ACh release from parasympathetic nerves innervating guinea-pig trachea through agonism of prostanoid receptors of the EP3-subtype. British journal of pharmacology 20040201
Inhibition of human glioma cell growth by a PHS-2 inhibitor, NS398, and a prostaglandin E receptor subtype EP1-selective antagonist, SC51089. Journal of neuro-oncology 20040201
Glutamate-mediated cytosolic calcium oscillations regulate a pulsatile prostaglandin release from cultured rat astrocytes. The Journal of physiology 20031201
Effects of mechanical strain on the function of Gap junctions in osteocytes are mediated through the prostaglandin EP2 receptor. The Journal of biological chemistry 20031031
Role of prostaglandin E2 receptors in migration of murine and human breast cancer cells. Experimental cell research 20031001
Leukotriene D4-induced adhesion of Caco-2 cells is mediated by prostaglandin E2 and upregulation of alpha2beta1-integrin. Experimental cell research 20031001
Modulation of guinea pig intrinsic cardiac neurons by prostaglandins. American journal of physiology. Regulatory, integrative and comparative physiology 20030901
Effects of PGE2 in guinea pig colonic myenteric ganglia. American journal of physiology. Gastrointestinal and liver physiology 20021201
Differential peristaltic motor effects of prostanoid (DP, EP, IP, TP) and leukotriene receptor agonists in the guinea-pig isolated small intestine. British journal of pharmacology 20021201
PGD(2) modulates fibroblast-mediated native collagen gel contraction. American journal of respiratory cell and molecular biology 20020901
AH6809 antagonizes non-small cell lung cancer prostaglandin receptors. Lung cancer (Amsterdam, Netherlands) 20020401
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques. The Journal of pharmacy and pharmacology 20020401
Role of EP(1) and EP(4) PGE(2) subtype receptors in serum-induced 3T6 fibroblast cycle progression and proliferation. American journal of physiology. Cell physiology 20020201
Trophic effects of the cyclooxygenase-2 product prostaglandin E(2) in cardiac myocytes. Hypertension (Dallas, Tex. : 1979) 20020201
Prostanoid EP(1)- and TP-receptors involved in the contraction of human pulmonary veins. British journal of pharmacology 20011201
Prostanoids stimulate K secretion and Cl secretion in guinea pig distal colon via distinct pathways. American journal of physiology. Gastrointestinal and liver physiology 20011001
Human granulosa-lutein cells express functional EP1 and EP2 prostaglandin receptors. Biochemical and biophysical research communications 20010803
Characterization of PGE2 receptors in fetal and newborn lamb ductus arteriosus. American journal of physiology. Heart and circulatory physiology 20010501
EP(4) receptors mediate prostaglandin E(2)-stimulated glycosaminoglycan synthesis in human cervical fibroblasts in culture. Molecular human reproduction 20010401
Role of PGE(2) in protease-activated receptor-1, -2 and -4 mediated relaxation in the mouse isolated trachea. British journal of pharmacology 20010101
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochimica et biophysica acta 20000117
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes. European journal of pharmacology 19971211
Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation. British journal of pharmacology 19970901
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. British journal of pharmacology 19970901
6-Isopropoxy-9-oxoxanthene-2-carboxylic acid (AH 6809), a human EP2 receptor antagonist. Biochemical pharmacology 19951109
Nociceptive effects induced by intrathecal administration of prostaglandin D2, E2, or F2 alpha to conscious mice. Brain research 19900226
Selective inhibition of prostaglandin E2 receptors EP2 and EP4 induces apoptosis of human endometriotic cells through suppression of ERK1/2, AKT, NFkappaB, and beta-catenin pathways and activation of intrinsic apoptotic mechanisms. Molecular endocrinology (Baltimore, Md.)
Estrogen receptor-related receptor alpha mediates up-regulation of aromatase expression by prostaglandin E2 in prostate stromal cells. Molecular endocrinology (Baltimore, Md.)
Properties