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39746-25-3,MFCD00151141
Catalog No.:AA0077D3

39746-25-3 | Prosta-5,13-dien-1-oicacid, 11,15-dihydroxy-16,16-dimethyl-9-oxo-, (5Z,11a,13E,15R)-

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1mg
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$123.00   $86.00
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5mg
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10mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0077D3
Chemical Name:
Prosta-5,13-dien-1-oicacid, 11,15-dihydroxy-16,16-dimethyl-9-oxo-, (5Z,11a,13E,15R)-
CAS Number:
39746-25-3
Molecular Formula:
C22H36O5
Molecular Weight:
380.5182
MDL Number:
MFCD00151141
SMILES:
CCCCC([C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)(C)C
Properties
Computed Properties
 
Complexity:
535  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
12  
XLogP3:
3.7  

Literature

Title: Autocrine prostaglandin E2 signaling promotes tumor cell survival and proliferation in childhood neuroblastoma.

Journal: PloS one 20120101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Chronic prostaglandin E2 treatment induces the synthesis of the pain-related peptide substance P and calcitonin gene-related peptide in cultured sensory ganglion explants.

Journal: Journal of neurochemistry 20101001

Title: Protective effect of lafutidine, a histamine H2 receptor antagonist, against loxoprofen-induced small intestinal lesions in rats.

Journal: Journal of gastroenterology and hepatology 20100501

Title: New method of inducing intestinal lesions in rats by intraduodenal administration of aspirin.

Journal: Journal of gastroenterology and hepatology 20100501

Title: Endogenous prostaglandin E2 accelerates healing of indomethacin-induced small intestinal lesions through upregulation of vascular endothelial growth factor expression by activation of EP4 receptors.

Journal: Journal of gastroenterology and hepatology 20100501

Title: 16,16-Dimethyl prostaglandin E2 efficacy on prevention and protection from bleomycin-induced lung injury and fibrosis.

Journal: American journal of respiratory cell and molecular biology 20090701

Title: Discovering chemical modifiers of oncogene-regulated hematopoietic differentiation.

Journal: Nature chemical biology 20090401

Title: Role of lipoxygenases and the lipoxin A(4)/annexin 1 receptor in ischemia-reperfusion-induced gastric mucosal damage in rats.

Journal: Pharmacology 20090101

Title: Prophylactic effect of irsogladine maleate against indomethacin-induced small intestinal lesions in rats.

Journal: Digestive diseases and sciences 20081001

Title: Decreased MAPK- and PGE2-dependent IL-11 production in Gialpha2-/- colonic myofibroblasts.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20070601

Title: Role of TGF-beta and PGE2 in T cell responses during Plasmodium yoelii infection.

Journal: European journal of immunology 20070601

Title: Effects of selective PGE2 receptor antagonists in esophageal adenocarcinoma cells derived from Barrett's esophagus.

Journal: Prostaglandins & other lipid mediators 20061201

Title: Roles of endogenous prostaglandins and cyclooxygenase isozymes in healing of indomethacin-induced small intestinal lesions in rats.

Journal: The Journal of pharmacology and experimental therapeutics 20060801

Title: Grapefruit-seed extract attenuates ethanol-and stress-induced gastric lesions via activation of prostaglandin, nitric oxide and sensory nerve pathways.

Journal: World journal of gastroenterology 20051107

Title: Comparison of prostaglandin and cimetidine in protection of isolated gastric glands against indomethacin injury.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20050901

Title: Functional mechanism underlying cyclooxygenase-2 expression in rat small intestine following administration of indomethacin: relation to intestinal hypermotility.

Journal: Journal of gastroenterology and hepatology 20050101

Title: Prostaglandin E2 reduces radiation-induced epithelial apoptosis through a mechanism involving AKT activation and bax translocation.

Journal: The Journal of clinical investigation 20041201

Title: Prostaglandin E2-dependent enhancement of tissue inhibitors of metalloproteinases-1 production limits dendritic cell migration through extracellular matrix.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20041101

Title: Prostaglandin E2--mediated relaxation of the ductus arteriosus: effects of gestational age on g protein-coupled receptor expression, signaling, and vasomotor control.

Journal: Circulation 20041019

Title: Hypoxia up-regulates the effects of prostaglandin E2 on tumor angiogenesis in ovarian cancer cells.

Journal: Gynecologic oncology 20040801

Title: Tumor growth inhibition by indomethacin in a mouse model of human medullary thyroid cancer: implication of cyclooxygenases and 15-hydroxyprostaglandin dehydrogenase.

Journal: Endocrinology 20040501

Title: TNFR1 mediates the radioprotective effects of lipopolysaccharide in the mouse intestine.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20040101

Title: 11-Deoxy,16,16-dimethyl prostaglandin E2 induces specific proteins in association with its ability to protect against oxidative stress.

Journal: Chemical research in toxicology 20030301

Title: PI3K signaling is required for prostaglandin-induced mucosal recovery in ischemia-injured porcine ileum.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20030101

Title: Role of ATP-sensitive potassium channels in prostaglandin-mediated gastroprotection in the rat.

Journal: The Journal of pharmacology and experimental therapeutics 20020601

Title: 16,16-Dimethyl prostaglandin E2 inhibits indomethacin-induced small intestinal lesions through EP3 and EP4 receptors.

Journal: Digestive diseases and sciences 20020401

Title: Prostaglandin E(2) protects intestinal tumors from nonsteroidal anti-inflammatory drug-induced regression in Apc(Min/+) mice.

Journal: Cancer research 20020115

Title: Protective effect of thiaton, an antispasmodic drug, against indomethacin-induced intestinal damage in rats.

Journal: Japanese journal of pharmacology 20020101

Title: Protective effect of rebamipide on indomethacin-induced intestinal damage in rats.

Journal: Journal of gastroenterology and hepatology 20011001

Title: Ischemic preconditioning, the most effective gastroprotective intervention: involvement of prostaglandins, nitric oxide, adenosine and sensory nerves.

Journal: European journal of pharmacology 20010921

Title: Secretion of the trefoil factor TFF3 from the isolated vascularly perfused rat colon.

Journal: Regulatory peptides 20010915

Title: Human granulosa-lutein cells express functional EP1 and EP2 prostaglandin receptors.

Journal: Biochemical and biophysical research communications 20010803

Title: Prostaglandin E prevents indomethacin-induced gastric and intestinal damage through different EP receptor subtypes.

Journal: Journal of physiology, Paris 20010101

Title: Epidermal growth factor and prostaglandin E(2) accelerate mucosal recovery from stress-induced gastric lesions via inhibition of apoptosis.

Journal: Journal of physiology, Paris 20010101

Title: Protective effect of lafutidine against indomethacin-induced intestinal ulceration in rats: relation to capsaicin-sensitive sensory neurons.

Journal: Digestion 20000101

Title: Developmental regulation of endothelial nitric oxide synthase in cerebral vessels of newborn pig by prostaglandin E(2).

Journal: The Journal of pharmacology and experimental therapeutics 19991101

Title: Induction of apoptotic DNA fragmentation by nonsteroidal anti-inflammatory drugs in cultured rat gastric mucosal cells.

Journal: European journal of pharmacology 19981106

Title: Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation.

Journal: British journal of pharmacology 19970901

Title: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.

Journal: British journal of pharmacology 19970901

Title: Apoptosis primarily accounts for the growth-inhibitory properties of sulindac metabolites and involves a mechanism that is independent of cyclooxygenase inhibition, cell cycle arrest, and p53 induction.

Journal: Cancer research 19970615

Title: Induction of cyclo-oxygenase-2 mRNA by prostaglandin E2 in human prostatic carcinoma cells.

Journal: British journal of cancer 19970101

Title: Role of beta-adrenoceptors in gastric mucosal integrity and gastroprotection induced by epidermal growth factor.

Journal: Digestion 19970101

Title: Attenuation of acetaminophen hepatitis by prostaglandin E2. A histopathological study.

Journal: Digestive diseases and sciences 19940501

Title: Studies on the mechanism of the protective action of 16,16-dimethylPGE2 in carbon tetrachloride induced acute hepatic injury in the rat.

Journal: Prostaglandins 19860901

Title: Failure of exogenous prostaglandin to afford complete protection against acetaminophen-induced hepatotoxicity in the rat.

Journal: Journal of toxicology and environmental health 19850101

Title: Protective effect of 16,16-dimethyl prostaglandin E2 on the hepatotoxicity of bromobenzene in mice.

Journal: Biochemical pharmacology 19840101

Title: Hagedorn EJ, et al. Getting more for your marrow: boosting hematopoietic stem cell numbers with PGE2. xp Cell Res. 2014 Dec 10;329(2):220-6.

Title: Roulis M, et al. Intestinal myofibroblast-specific Tpl2-Cox-2-PGE2 pathway links innate sensing to epithelial homeostasis. Proc Natl Acad Sci U S A. 2014 Oct 28;111(43):E4658-67.

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Tags:39746-25-3 Molecular Formula|39746-25-3 MDL|39746-25-3 SMILES|39746-25-3 Prosta-5,13-dien-1-oicacid, 11,15-dihydroxy-16,16-dimethyl-9-oxo-, (5Z,11a,13E,15R)-