1449-05-4,MFCD00064897
Catalog No.:AA001K8U

1449-05-4 | Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3β,18α,20β)-

Pack Size
Purity
Availability
Price(USD)
Quantity
  
25mg
99%
1 week  
$130.00   $91.00
- +
50mg
99%
1 week  
$177.00   $124.00
- +
100mg
99%
1 week  
$241.00   $169.00
- +
  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA001K8U
Chemical Name:
Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3β,18α,20β)-
CAS Number:
1449-05-4
Molecular Formula:
C30H46O4
Molecular Weight:
470.6838
MDL Number:
MFCD00064897
SMILES:
O=C1C=C2[C@H]3C[C@](C)(CC[C@]3(C)CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C(C1CC2)(C)C)O)C)C)C(=O)O
Properties
Computed Properties
 
Complexity:
965  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
1  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
6.4  

Literature

Title: Gap junctional intercellular communication and endoplasmic reticulum stress regulate chronic cadmium exposure induced apoptosis in HK-2 cells.

Journal: Toxicology letters 20180515

Title: Glycyrrhizin and glycyrrhetinic acid inhibits alpha-naphthyl isothiocyanate-induced liver injury and bile acid cycle disruption.

Journal: Toxicology 20170701

Title: Methotrexate hepatotoxicity is associated with oxidative stress, and down-regulation of PPARγ and Nrf2: Protective effect of 18β-Glycyrrhetinic acid.

Journal: Chemico-biological interactions 20170525

Title: 18β-Glycyrrhetinic acid suppresses TNF-α induced matrix metalloproteinase-9 and vascular endothelial growth factor by suppressing the Akt-dependent NF-κB pathway.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20140801

Title: Purinergic signaling via P2Y receptors up-mediates IL-6 production by liver macrophages/Kupffer cells.

Journal: The Journal of toxicological sciences 20140601

Title: Inhibitory effects of herbal constituents on P-glycoprotein in vitro and in vivo: herb-drug interactions mediated via P-gp.

Journal: Toxicology and applied pharmacology 20140301

Title: Anti-diabetic and anti-inflammatory effect of a novel selective 11β-HSD1 inhibitor in the diet-induced obese mice.

Journal: European journal of pharmacology 20131205

Title: 18β-glycyrrhetinic acid potentiates Hsp90 inhibition-induced apoptosis in human epithelial ovarian carcinoma cells via activation of death receptor and mitochondrial pathway.

Journal: Molecular and cellular biochemistry 20121101

Title: The blood-brain barrier permeability of 18β-glycyrrhetinic acid, a major metabolite of glycyrrhizin in Glycyrrhiza root, a constituent of the traditional Japanese medicine yokukansan.

Journal: Cellular and molecular neurobiology 20121001

Title: Myoendothelial coupling is unidirectional in guinea pig spiral modiolar arteries.

Journal: Microvascular research 20120901

Title: Mitochondrial connexin 43 impacts on respiratory complex I activity and mitochondrial oxygen consumption.

Journal: Journal of cellular and molecular medicine 20120801

Title: Laminin-111 stimulates proliferation of mouse embryonic stem cells through a reduction of gap junctional intercellular communication via RhoA-mediated Cx43 phosphorylation and dissociation of Cx43/ZO-1/drebrin complex.

Journal: Stem cells and development 20120720

Title: Enhanced transdermal delivery of 18β-glycyrrhetic acid via elastic vesicles: in vitro and in vivo evaluation.

Journal: Drug development and industrial pharmacy 20120701

Title: TRPV4 in porcine lens epithelium regulates hemichannel-mediated ATP release and Na-K-ATPase activity.

Journal: American journal of physiology. Cell physiology 20120615

Title: The anti-ulcer agent, irsogladine, increases insulin secretion by MIN6 cells.

Journal: European journal of pharmacology 20120615

Title: 18β-Glycyrrhetinic acid preferentially blocks late Na current generated by ΔKPQ Nav1.5 channels.

Journal: Acta pharmacologica Sinica 20120601

Title: 18β-glycyrrhetinic acid induces apoptosis through modulation of Akt/FOXO3a/Bim pathway in human breast cancer MCF-7 cells.

Journal: Journal of cellular physiology 20120501

Title: Gap junctions propagate opposite effects in normal and tumor testicular cells in response to cisplatin.

Journal: Cancer letters 20120428

Title: 18β-Glycyrrhetinic acid inhibits adipogenic differentiation and stimulates lipolysis.

Journal: Biochemical and biophysical research communications 20120420

Title: ERK acts in parallel to PKCδ to mediate the connexin43-dependent potentiation of Runx2 activity by FGF2 in MC3T3 osteoblasts.

Journal: American journal of physiology. Cell physiology 20120401

Title: Inhibition of gap junction channel attenuates the migration of breast cancer cells.

Journal: Molecular biology reports 20120301

Title: Effects of 18β-Glycyrrhetinic acid in hTNFtg mice - a model of rheumatoid arthritis.

Journal: Wiener klinische Wochenschrift 20120301

Title: Antimycobacterial and synergistic effects of 18β-glycyrrhetinic acid or glycyrrhetinic acid-30-piperazine in combination with isoniazid, rifampicin or streptomycin against Mycobacterium bovis.

Journal: Phytotherapy research : PTR 20120201

Title: Characterization of a novel oral glucocorticoid system and its possible role in disease.

Journal: Journal of dental research 20120101

Title: Endothelium-derived relaxing factor-mediated vasodilation in mouse mesenteric vascular beds.

Journal: Journal of pharmacological sciences 20120101

Title: Pharmacokinetic analysis of alpha and beta epimers of glycyrrhetinic acid in rat plasma: differences in singly and combined administrations.

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20120101

Title: 18α-glycyrrhetinic acid down-regulates expression of type I and III collagen via TGF-Β1/Smad signaling pathway in human and rat hepatic stellate cells.

Journal: International journal of medical sciences 20120101

Title: A novel transdermal fomulation of 18β-glycyrrhetic acid with lysine for improving bioavailability and efficacy.

Journal: Skin pharmacology and physiology 20120101

Title: Gap junctions contribute to astrocytic resistance against zinc toxicity.

Journal: Brain research bulletin 20111125

Title: Disruption of gap junctions reduces biomarkers of decidualization and angiogenesis and increases inflammatory mediators in human endometrial stromal cell cultures.

Journal: Molecular and cellular endocrinology 20110915

Title: 18α-glycyrrhetinic acid targets prostate cancer cells by down-regulating inflammation-related genes.

Journal: International journal of oncology 20110901

Title: Therapeutic effects of connexin inhibitors on detrusor overactivity induced by bladder outlet obstruction in rats.

Journal: Urology 20110801

Title: Inhibition of osteoblastic differentiation by warfarin and 18-α-glycyrrhetinic acid.

Journal: Archives of pharmacal research 20110801

Title: Glycyrrhizic acid and 18β-glycyrrhetinic acid modulate lipopolysaccharide-induced inflammatory response by suppression of NF-κB through PI3K p110δ and p110γ inhibitions.

Journal: Journal of agricultural and food chemistry 20110727

Title: 18β-Glycyrrhetinic acid derivatives induced mitochondrial-mediated apoptosis through reactive oxygen species-mediated p53 activation in NTUB1 cells.

Journal: Bioorganic & medicinal chemistry 20110715

Title: 18β-glycyrrhetic acid inhibits immune activation triggered by HMGB1, a pro-inflammatory protein found in the tear fluid during conjunctivitis and blepharitis.

Journal: Ocular immunology and inflammation 20110601

Title: 18beta-glycyrrhetinic acid and glabridin prevent oxidative DNA fragmentation in UVB-irradiated human keratinocyte cultures.

Journal: Anticancer research 20110601

Title: Chemopreventive potential of 18beta-glycyrrhetinic acid: an active constituent of liquorice, in 7,12-dimethylbenz(a)anthracene induced hamster buccal pouch carcinogenesis.

Journal: Pakistan journal of biological sciences : PJBS 20110601

Title: Effects of connexin-mimetic peptides on perfusion pressure in response to phenylephrine in isolated, perfused rat kidneys.

Journal: Clinical and experimental nephrology 20110401

Title: Design, synthesis, and sustained-release property of 1,3-cyclic propanyl phosphate ester of 18β-glycyrrhetinic acid.

Journal: Chemical biology & drug design 20110301

Title: [Expression of 11β-hydroxysteroid dehydrogenase type 2 in lymphoblastic cells and its relationship with glucocorticoid sensitivity].

Journal: Zhongguo shi yan xue ye xue za zhi 20110201

Title: Intercellular communication amplifies stressful effects in high-charge, high-energy (HZE) particle-irradiated human cells.

Journal: Journal of radiation research 20110101

Title: Curative effect of 18β-glycyrrhetinic acid in experimental visceral leishmaniasis depends on phosphatase-dependent modulation of cellular MAP kinases.

Journal: PloS one 20110101

Title: 18β-Glycyrrhetinic acid potentiates apoptotic effect of trichostatin A on human epithelial ovarian carcinoma cell lines.

Journal: European journal of pharmacology 20101215

Title: Specific brainstem neurons switch each other into pacemaker mode to drive movement by activating NMDA receptors.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20101208

Title: 18β-glycyrrhetinic acid inhibits periodontitis via glucocorticoid-independent nuclear factor-κB inactivation in interleukin-10-deficient mice.

Journal: Journal of periodontal research 20101201

Title: Role of connexin 43 in the maintenance of spontaneous activity in the guinea pig prostate gland.

Journal: British journal of pharmacology 20101201

Title: Cytoplasm and organelle transfer between mesenchymal multipotent stromal cells and renal tubular cells in co-culture.

Journal: Experimental cell research 20100910

Title: Glycyrrhizic acid and 18beta-glycyrrhetinic acid inhibit inflammation via PI3K/Akt/GSK3beta signaling and glucocorticoid receptor activation.

Journal: Journal of agricultural and food chemistry 20100811

Title: Connexin 43 hemichannel regulates H9c2 cell proliferation by modulating intracellular ATP and [Ca2+].

Journal: Acta biochimica et biophysica Sinica 20100701

Title: Nuclear erythroid factor 2-mediated proteasome activation delays senescence in human fibroblasts.

Journal: The Journal of biological chemistry 20100312

Title: Gap junctions and memory: an investigation using a single trial discrimination avoidance task for the neonate chick.

Journal: Neurobiology of learning and memory 20100201

Title: Glycyrrhizin and its metabolite 18 beta-glycyrrhetinic acid in glycyrrhiza, a constituent herb of yokukansan, ameliorate thiamine deficiency-induced dysfunction of glutamate transport in cultured rat cortical astrocytes.

Journal: European journal of pharmacology 20100125

Title: 18Beta-glycyrrhetinic acid ameliorates acute Propionibacterium acnes-induced liver injury through inhibition of macrophage inflammatory protein-1alpha.

Journal: The Journal of biological chemistry 20100108

Title: Mechanism underlying endothelium-dependent relaxation by 2-methylthio-ADP in monkey cerebral artery.

Journal: Journal of pharmacological sciences 20100101

Title: Panax notoginseng saponins potentiate osteogenesis of bone marrow stromal cells by modulating gap junction intercellular communication activities.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20100101

Title: Role of connexin-43 hemichannels in the pathogenesis of Yersinia enterocolitica.

Journal: Veterinary journal (London, England : 1997) 20091201

Title: Tramadol and flurbiprofen depress the cytotoxicity of cisplatin via their effects on gap junctions.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090915

Title: Glycyrrhizin prevents 7-ketocholesterol toxicity against differentiated PC12 cells by suppressing mitochondrial membrane permeability change.

Journal: Neurochemical research 20090801

Title: Direct formation of proteo-liposomes by in vitro synthesis and cellular cytosolic delivery with connexin-expressing liposomes.

Journal: Biomaterials 20090801

Title: A heterotypic bystander effect for tumor cell killing after adeno-associated virus/phage-mediated, vascular-targeted suicide gene transfer.

Journal: Molecular cancer therapeutics 20090801

Title: Infusion of gliotoxins or a gap junction blocker in the prelimbic cortex increases alcohol preference in Wistar rats.

Journal: Journal of psychopharmacology (Oxford, England) 20090701

Title: Hypolipidemic activity of 18beta-glycyrrhetinic acid on streptozotocin-induced diabetic rats.

Journal: European journal of pharmacology 20090610

Title: Effect of gap junction blocker beta-glycyrrhetinic acid on taste disk cells in frog.

Journal: Cellular and molecular neurobiology 20090601

Title: In vitro effects of glycyrrhetinic acid on the growth of clinical isolates of Candida albicans.

Journal: Phytotherapy research : PTR 20090401

Title: Locomotor rhythm maintenance: electrical coupling among premotor excitatory interneurons in the brainstem and spinal cord of young Xenopus tadpoles.

Journal: The Journal of physiology 20090401

Title: Antihyperglycemic effect of 18 beta-glycyrrhetinic acid, aglycone of glycyrrhizin, on streptozotocin-diabetic rats.

Journal: European journal of pharmacology 20090315

Title: Possible participation of chloride ion channels in ATP release from cancer cells in suspension.

Journal: Clinical and experimental pharmacology & physiology 20090301

Title: ATP release by cardiac myocytes in a simulated ischaemia model: inhibition by a connexin mimetic and enhancement by an antiarrhythmic peptide.

Journal: European journal of pharmacology 20090301

Title: Pharmacological 'cross-inhibition' of connexin hemichannels and swelling activated anion channels.

Journal: Glia 20090201

Title: Perturbing plasma membrane hemichannels attenuates calcium signalling in cardiac cells and HeLa cells expressing connexins.

Journal: European journal of cell biology 20090201

Title: Selective inhibition of 11beta-hydroxysteroid dehydrogenase 1 by 18alpha-glycyrrhetinic acid but not 18beta-glycyrrhetinic acid.

Journal: The Journal of steroid biochemistry and molecular biology 20090201

Title: Neuroprotective effects of glycyrrhizic acid and 18beta-glycyrrhetinic acid in PC12 cells via modulation of the PI3K/Akt pathway.

Journal: Journal of agricultural and food chemistry 20090128

Title: The role of gap junctions in megakaryocyte-mediated osteoblast proliferation and differentiation.

Journal: Bone 20090101

Title: Simultaneous determination of 18alpha- and 18beta-glycyrrhetic acid in human plasma by LC-ESI-MS and its application to pharmacokinetics.

Journal: Biomedical chromatography : BMC 20090101

Title: Regulatory effects of myoendothelial gap junction on vascular reactivity after hemorrhagic shock in rats.

Journal: Shock (Augusta, Ga.) 20090101

Title: Microbial transformation of 18beta-glycyrrhetinic acid by Cunninghamella elegans and Fusarium lini, and lipoxygenase inhibitory activity of transformed products.

Journal: Natural product research 20090101

Title: 18beta-Glycyrrhetinic acid induces apoptotic cell death in SiHa cells and exhibits a synergistic effect against antibiotic anti-cancer drug toxicity.

Journal: Life sciences 20080926

Title: Enhanced spontaneous Ca2+ events in endothelial cells reflect signalling through myoendothelial gap junctions in pressurized mesenteric arteries.

Journal: Cell calcium 20080801

Title: Prevention of free fatty acid-induced hepatic lipotoxicity by 18beta-glycyrrhetinic acid through lysosomal and mitochondrial pathways.

Journal: Hepatology (Baltimore, Md.) 20080601

Title: Targeting connexin 43 prevents platelet-derived growth factor-BB-induced phenotypic change in porcine coronary artery smooth muscle cells.

Journal: Circulation research 20080328

Title: Role of gap junctions and protein kinase A during the development of oocyte maturational competence in Ayu (Plecoglossus altivelis).

Journal: General and comparative endocrinology 20080201

Title: Endothelium-derived hyperpolarizing factor in preeclampsia: heterogeneous contribution, mechanisms, and morphological prerequisites.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20080201

Title: Role of gap junctions in spontaneous activity of the rat bladder.

Journal: American journal of physiology. Renal physiology 20071001

Title: Spontaneous electrical and Ca2+ signals in typical and atypical smooth muscle cells and interstitial cell of Cajal-like cells of mouse renal pelvis.

Journal: The Journal of physiology 20070915

Title: Blockade of gap junction coupling by glycyrrhetinic acids in guinea pig cochlear artery: a whole-cell voltage- and current-clamp study.

Journal: British journal of pharmacology 20070801

Title: Protein kinase C gamma mutations in the C1B domain cause caspase-3-linked apoptosis in lens epithelial cells through gap junctions.

Journal: Experimental eye research 20070701

Title: Primary cultures of chick osteocytes retain functional gap junctions between osteocytes and between osteocytes and osteoblasts.

Journal: Microscopy and microanalysis : the official journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada 20070401

Title: 18alpha-glycyrrhetinic acid induces phenotypic changes of skeletal muscle cells to enter adipogenesis.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20070101

Title: The function of connexin 43 on the differentiation of rat bone marrow cells in culture.

Journal: Biomedical research (Tokyo, Japan) 20061201

Title: A gap junction blocker inhibits isolated whole bladder activity in normal rats and rats with partial bladder outlet obstruction.

Journal: Biomedical research (Tokyo, Japan) 20061001

Title: The role of connexins in the differentiation of NT2 cells in Sertoli-NT2 cell tissue constructs grown in the rotating wall bioreactor.

Journal: Experimental brain research 20060401

Title: Protective effect of gap junction uncouplers given during hypoxia against reoxygenation injury in isolated rat hearts.

Journal: American journal of physiology. Heart and circulatory physiology 20060201

Title: Role of gap junctional coupling in astrocytic networks in the determination of global ischaemia-induced oxidative stress and hippocampal damage.

Journal: The European journal of neuroscience 20060101

Title: Staphylococcus aureus-derived peptidoglycan induces Cx43 expression and functional gap junction intercellular communication in microglia.

Journal: Journal of neurochemistry 20051001

Title: Licorice compounds glycyrrhizin and 18beta-glycyrrhetinic acid are potent modulators of bile acid-induced cytotoxicity in rat hepatocytes.

Journal: The Journal of biological chemistry 20050318

Title: Adenoviral delivery of human connexin37 induces endothelial cell death through apoptosis.

Journal: Biochemical and biophysical research communications 20040709

Title: Prostaglandin F2alpha amplifies tumor necrosis factor-alpha promoter activity by the FPB prostanoid receptor.

Journal: Biochemical and biophysical research communications 20040514

Title: Global, synchronous oscillations in cytosolic calcium and adherence in bradykinin-stimulated Madin-Darby canine kidney cells.

Journal: Acta physiologica Scandinavica 20040401

Title: Cytogenetic detection of a trans-species bystander effect: induction of sister chromatid exchanges in murine 3T3 cells by ganciclovir metabolized in HSV thymidine kinase gene-transfected Chinese hamster ovary cells.

Journal: Mutagenesis 20040101

Title: Human primary endothelial cells stimulate human osteoprogenitor cell differentiation.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20040101

Title: [Involvement of gap junctions in stimulation of in vitro maturation of the common frog oocytes by low progesterone concentrations].

Journal: Ontogenez 20040101

Title: ECM-induced gap junctional communication enhances mammary epithelial cell differentiation.

Journal: Journal of cell science 20030901

Title: Intercellular calcium waves mediate preferential cell growth toward the wound edge in polarized hepatic cells.

Journal: Experimental cell research 20030715

Title: Functional hemichannels in astrocytes: a novel mechanism of glutamate release.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20030501

Title: Expression of connexin 43 mRNA in microisolated murine osteoclasts and regulation of bone resorption in vitro by gap junction inhibitors.

Journal: Biochemical and biophysical research communications 20030418

Title: Blockade of brain stem gap junctions increases phrenic burst frequency and reduces phrenic burst synchronization in adult rat.

Journal: Journal of neurophysiology 20030101

Title: Inhibitors of gap junctions attenuate myogenic tone in cerebral arteries.

Journal: American journal of physiology. Heart and circulatory physiology 20021201

Title: Bone morphogenetic protein-2 modulation of chondrogenic differentiation in vitro involves gap junction-mediated intercellular communication.

Journal: Journal of cellular physiology 20021101

Title: The role of gap junctions in mediating endothelium-dependent responses to bradykinin in myometrial small arteries isolated from pregnant women.

Journal: British journal of pharmacology 20020801

Title: Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries.

Journal: Clinical and experimental pharmacology & physiology 20020701

Title: Hydrogen peroxide is an endothelium-derived hyperpolarizing factor in human mesenteric arteries.

Journal: Biochemical and biophysical research communications 20020125

Title: Bimodal inhibition of connexin 43 gap junctions decreases ACTH-induced steroidogenesis and increases bovine adrenal cell population growth.

Journal: The Journal of endocrinology 20011001

Title: An endothelium-derived hyperpolarizing factor-like factor moderates myogenic constriction of mesenteric resistance arteries in the absence of endothelial nitric oxide synthase-derived nitric oxide.

Journal: Hypertension (Dallas, Tex. : 1979) 20011001

Title: Dual mechanism of intercellular communication in HOBIT osteoblastic cells: a role for gap-junctional hemichannels.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20010801

Title: Persistence of gap junction communication during myocardial ischemia.

Journal: American journal of physiology. Heart and circulatory physiology 20010601

Title: Endothelium-dependent vasorelaxation independent of nitric oxide and K(+) release in isolated renal arteries of rats.

Journal: British journal of pharmacology 20010401

Title: Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.

Journal: Molecular and cellular endocrinology 20010122

Title: Blockade of chloride channels reveals relaxations of rat small mesenteric arteries to raised potassium.

Journal: British journal of pharmacology 20010101

Title: Zong L et al. 18α-glycyrrhetinic acid extracted from Glycyrrhiza radix inhibits proliferation and promotes apoptosis of the hepatic stellate cell line. J Dig Dis. 2013 Jun;14(6):328-36.

Title: Papaevgeniou N, et al. 18α-Glycyrrhetinic Acid Proteasome Activator Decelerates Aging and Alzheimer's Disease Progression in Caenorhabditis elegans and Neuronal Cultures. Antioxid Redox Signal. 2016 Dec 1;25(16):855-869.

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Tags:1449-05-4 Molecular Formula|1449-05-4 MDL|1449-05-4 SMILES|1449-05-4 Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3β,18α,20β)-
Catalog No.: AA001K8U
1449-05-4,MFCD00064897
1449-05-4 | Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3β,18α,20β)-
Pack Size: 25mg
Purity: 99%
1 week
$130.00 $91.00
Pack Size: 50mg
Purity: 99%
1 week
$177.00 $124.00
Pack Size: 100mg
Purity: 99%
1 week
$241.00 $169.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA001K8U
Chemical Name: Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3β,18α,20β)-
CAS Number: 1449-05-4
Molecular Formula: C30H46O4
Molecular Weight: 470.6838
MDL Number: MFCD00064897
SMILES: O=C1C=C2[C@H]3C[C@](C)(CC[C@]3(C)CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C(C1CC2)(C)C)O)C)C)C(=O)O
Properties
Complexity: 965  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 9  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 34  
Hydrogen Bond Acceptor Count: 4  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 1  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 6.4  
Literature fold

Title: Gap junctional intercellular communication and endoplasmic reticulum stress regulate chronic cadmium exposure induced apoptosis in HK-2 cells.

Journal: Toxicology letters20180515

Title: Glycyrrhizin and glycyrrhetinic acid inhibits alpha-naphthyl isothiocyanate-induced liver injury and bile acid cycle disruption.

Journal: Toxicology20170701

Title: Methotrexate hepatotoxicity is associated with oxidative stress, and down-regulation of PPARγ and Nrf2: Protective effect of 18β-Glycyrrhetinic acid.

Journal: Chemico-biological interactions20170525

Title: 18β-Glycyrrhetinic acid suppresses TNF-α induced matrix metalloproteinase-9 and vascular endothelial growth factor by suppressing the Akt-dependent NF-κB pathway.

Journal: Toxicology in vitro : an international journal published in association with BIBRA20140801

Title: Purinergic signaling via P2Y receptors up-mediates IL-6 production by liver macrophages/Kupffer cells.

Journal: The Journal of toxicological sciences20140601

Title: Inhibitory effects of herbal constituents on P-glycoprotein in vitro and in vivo: herb-drug interactions mediated via P-gp.

Journal: Toxicology and applied pharmacology20140301

Title: Anti-diabetic and anti-inflammatory effect of a novel selective 11β-HSD1 inhibitor in the diet-induced obese mice.

Journal: European journal of pharmacology20131205

Title: 18β-glycyrrhetinic acid potentiates Hsp90 inhibition-induced apoptosis in human epithelial ovarian carcinoma cells via activation of death receptor and mitochondrial pathway.

Journal: Molecular and cellular biochemistry20121101

Title: The blood-brain barrier permeability of 18β-glycyrrhetinic acid, a major metabolite of glycyrrhizin in Glycyrrhiza root, a constituent of the traditional Japanese medicine yokukansan.

Journal: Cellular and molecular neurobiology20121001

Title: Myoendothelial coupling is unidirectional in guinea pig spiral modiolar arteries.

Journal: Microvascular research20120901

Title: Mitochondrial connexin 43 impacts on respiratory complex I activity and mitochondrial oxygen consumption.

Journal: Journal of cellular and molecular medicine20120801

Title: Laminin-111 stimulates proliferation of mouse embryonic stem cells through a reduction of gap junctional intercellular communication via RhoA-mediated Cx43 phosphorylation and dissociation of Cx43/ZO-1/drebrin complex.

Journal: Stem cells and development20120720

Title: Enhanced transdermal delivery of 18β-glycyrrhetic acid via elastic vesicles: in vitro and in vivo evaluation.

Journal: Drug development and industrial pharmacy20120701

Title: TRPV4 in porcine lens epithelium regulates hemichannel-mediated ATP release and Na-K-ATPase activity.

Journal: American journal of physiology. Cell physiology20120615

Title: The anti-ulcer agent, irsogladine, increases insulin secretion by MIN6 cells.

Journal: European journal of pharmacology20120615

Title: 18β-Glycyrrhetinic acid preferentially blocks late Na current generated by ΔKPQ Nav1.5 channels.

Journal: Acta pharmacologica Sinica20120601

Title: 18β-glycyrrhetinic acid induces apoptosis through modulation of Akt/FOXO3a/Bim pathway in human breast cancer MCF-7 cells.

Journal: Journal of cellular physiology20120501

Title: Gap junctions propagate opposite effects in normal and tumor testicular cells in response to cisplatin.

Journal: Cancer letters20120428

Title: 18β-Glycyrrhetinic acid inhibits adipogenic differentiation and stimulates lipolysis.

Journal: Biochemical and biophysical research communications20120420

Title: ERK acts in parallel to PKCδ to mediate the connexin43-dependent potentiation of Runx2 activity by FGF2 in MC3T3 osteoblasts.

Journal: American journal of physiology. Cell physiology20120401

Title: Inhibition of gap junction channel attenuates the migration of breast cancer cells.

Journal: Molecular biology reports20120301

Title: Effects of 18β-Glycyrrhetinic acid in hTNFtg mice - a model of rheumatoid arthritis.

Journal: Wiener klinische Wochenschrift20120301

Title: Antimycobacterial and synergistic effects of 18β-glycyrrhetinic acid or glycyrrhetinic acid-30-piperazine in combination with isoniazid, rifampicin or streptomycin against Mycobacterium bovis.

Journal: Phytotherapy research : PTR20120201

Title: Characterization of a novel oral glucocorticoid system and its possible role in disease.

Journal: Journal of dental research20120101

Title: Endothelium-derived relaxing factor-mediated vasodilation in mouse mesenteric vascular beds.

Journal: Journal of pharmacological sciences20120101

Title: Pharmacokinetic analysis of alpha and beta epimers of glycyrrhetinic acid in rat plasma: differences in singly and combined administrations.

Journal: Yao xue xue bao = Acta pharmaceutica Sinica20120101

Title: 18α-glycyrrhetinic acid down-regulates expression of type I and III collagen via TGF-Β1/Smad signaling pathway in human and rat hepatic stellate cells.

Journal: International journal of medical sciences20120101

Title: A novel transdermal fomulation of 18β-glycyrrhetic acid with lysine for improving bioavailability and efficacy.

Journal: Skin pharmacology and physiology20120101

Title: Gap junctions contribute to astrocytic resistance against zinc toxicity.

Journal: Brain research bulletin20111125

Title: Disruption of gap junctions reduces biomarkers of decidualization and angiogenesis and increases inflammatory mediators in human endometrial stromal cell cultures.

Journal: Molecular and cellular endocrinology20110915

Title: 18α-glycyrrhetinic acid targets prostate cancer cells by down-regulating inflammation-related genes.

Journal: International journal of oncology20110901

Title: Therapeutic effects of connexin inhibitors on detrusor overactivity induced by bladder outlet obstruction in rats.

Journal: Urology20110801

Title: Inhibition of osteoblastic differentiation by warfarin and 18-α-glycyrrhetinic acid.

Journal: Archives of pharmacal research20110801

Title: Glycyrrhizic acid and 18β-glycyrrhetinic acid modulate lipopolysaccharide-induced inflammatory response by suppression of NF-κB through PI3K p110δ and p110γ inhibitions.

Journal: Journal of agricultural and food chemistry20110727

Title: 18β-Glycyrrhetinic acid derivatives induced mitochondrial-mediated apoptosis through reactive oxygen species-mediated p53 activation in NTUB1 cells.

Journal: Bioorganic & medicinal chemistry20110715

Title: 18β-glycyrrhetic acid inhibits immune activation triggered by HMGB1, a pro-inflammatory protein found in the tear fluid during conjunctivitis and blepharitis.

Journal: Ocular immunology and inflammation20110601

Title: 18beta-glycyrrhetinic acid and glabridin prevent oxidative DNA fragmentation in UVB-irradiated human keratinocyte cultures.

Journal: Anticancer research20110601

Title: Chemopreventive potential of 18beta-glycyrrhetinic acid: an active constituent of liquorice, in 7,12-dimethylbenz(a)anthracene induced hamster buccal pouch carcinogenesis.

Journal: Pakistan journal of biological sciences : PJBS20110601

Title: Effects of connexin-mimetic peptides on perfusion pressure in response to phenylephrine in isolated, perfused rat kidneys.

Journal: Clinical and experimental nephrology20110401

Title: Design, synthesis, and sustained-release property of 1,3-cyclic propanyl phosphate ester of 18β-glycyrrhetinic acid.

Journal: Chemical biology & drug design20110301

Title: [Expression of 11β-hydroxysteroid dehydrogenase type 2 in lymphoblastic cells and its relationship with glucocorticoid sensitivity].

Journal: Zhongguo shi yan xue ye xue za zhi20110201

Title: Intercellular communication amplifies stressful effects in high-charge, high-energy (HZE) particle-irradiated human cells.

Journal: Journal of radiation research20110101

Title: Curative effect of 18β-glycyrrhetinic acid in experimental visceral leishmaniasis depends on phosphatase-dependent modulation of cellular MAP kinases.

Journal: PloS one20110101

Title: 18β-Glycyrrhetinic acid potentiates apoptotic effect of trichostatin A on human epithelial ovarian carcinoma cell lines.

Journal: European journal of pharmacology20101215

Title: Specific brainstem neurons switch each other into pacemaker mode to drive movement by activating NMDA receptors.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience20101208

Title: 18β-glycyrrhetinic acid inhibits periodontitis via glucocorticoid-independent nuclear factor-κB inactivation in interleukin-10-deficient mice.

Journal: Journal of periodontal research20101201

Title: Role of connexin 43 in the maintenance of spontaneous activity in the guinea pig prostate gland.

Journal: British journal of pharmacology20101201

Title: Cytoplasm and organelle transfer between mesenchymal multipotent stromal cells and renal tubular cells in co-culture.

Journal: Experimental cell research20100910

Title: Glycyrrhizic acid and 18beta-glycyrrhetinic acid inhibit inflammation via PI3K/Akt/GSK3beta signaling and glucocorticoid receptor activation.

Journal: Journal of agricultural and food chemistry20100811

Title: Connexin 43 hemichannel regulates H9c2 cell proliferation by modulating intracellular ATP and [Ca2+].

Journal: Acta biochimica et biophysica Sinica20100701

Title: Nuclear erythroid factor 2-mediated proteasome activation delays senescence in human fibroblasts.

Journal: The Journal of biological chemistry20100312

Title: Gap junctions and memory: an investigation using a single trial discrimination avoidance task for the neonate chick.

Journal: Neurobiology of learning and memory20100201

Title: Glycyrrhizin and its metabolite 18 beta-glycyrrhetinic acid in glycyrrhiza, a constituent herb of yokukansan, ameliorate thiamine deficiency-induced dysfunction of glutamate transport in cultured rat cortical astrocytes.

Journal: European journal of pharmacology20100125

Title: 18Beta-glycyrrhetinic acid ameliorates acute Propionibacterium acnes-induced liver injury through inhibition of macrophage inflammatory protein-1alpha.

Journal: The Journal of biological chemistry20100108

Title: Mechanism underlying endothelium-dependent relaxation by 2-methylthio-ADP in monkey cerebral artery.

Journal: Journal of pharmacological sciences20100101

Title: Panax notoginseng saponins potentiate osteogenesis of bone marrow stromal cells by modulating gap junction intercellular communication activities.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology20100101

Title: Role of connexin-43 hemichannels in the pathogenesis of Yersinia enterocolitica.

Journal: Veterinary journal (London, England : 1997)20091201

Title: Tramadol and flurbiprofen depress the cytotoxicity of cisplatin via their effects on gap junctions.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20090915

Title: Glycyrrhizin prevents 7-ketocholesterol toxicity against differentiated PC12 cells by suppressing mitochondrial membrane permeability change.

Journal: Neurochemical research20090801

Title: Direct formation of proteo-liposomes by in vitro synthesis and cellular cytosolic delivery with connexin-expressing liposomes.

Journal: Biomaterials20090801

Title: A heterotypic bystander effect for tumor cell killing after adeno-associated virus/phage-mediated, vascular-targeted suicide gene transfer.

Journal: Molecular cancer therapeutics20090801

Title: Infusion of gliotoxins or a gap junction blocker in the prelimbic cortex increases alcohol preference in Wistar rats.

Journal: Journal of psychopharmacology (Oxford, England)20090701

Title: Hypolipidemic activity of 18beta-glycyrrhetinic acid on streptozotocin-induced diabetic rats.

Journal: European journal of pharmacology20090610

Title: Effect of gap junction blocker beta-glycyrrhetinic acid on taste disk cells in frog.

Journal: Cellular and molecular neurobiology20090601

Title: In vitro effects of glycyrrhetinic acid on the growth of clinical isolates of Candida albicans.

Journal: Phytotherapy research : PTR20090401

Title: Locomotor rhythm maintenance: electrical coupling among premotor excitatory interneurons in the brainstem and spinal cord of young Xenopus tadpoles.

Journal: The Journal of physiology20090401

Title: Antihyperglycemic effect of 18 beta-glycyrrhetinic acid, aglycone of glycyrrhizin, on streptozotocin-diabetic rats.

Journal: European journal of pharmacology20090315

Title: Possible participation of chloride ion channels in ATP release from cancer cells in suspension.

Journal: Clinical and experimental pharmacology & physiology20090301

Title: ATP release by cardiac myocytes in a simulated ischaemia model: inhibition by a connexin mimetic and enhancement by an antiarrhythmic peptide.

Journal: European journal of pharmacology20090301

Title: Pharmacological 'cross-inhibition' of connexin hemichannels and swelling activated anion channels.

Journal: Glia20090201

Title: Perturbing plasma membrane hemichannels attenuates calcium signalling in cardiac cells and HeLa cells expressing connexins.

Journal: European journal of cell biology20090201

Title: Selective inhibition of 11beta-hydroxysteroid dehydrogenase 1 by 18alpha-glycyrrhetinic acid but not 18beta-glycyrrhetinic acid.

Journal: The Journal of steroid biochemistry and molecular biology20090201

Title: Neuroprotective effects of glycyrrhizic acid and 18beta-glycyrrhetinic acid in PC12 cells via modulation of the PI3K/Akt pathway.

Journal: Journal of agricultural and food chemistry20090128

Title: The role of gap junctions in megakaryocyte-mediated osteoblast proliferation and differentiation.

Journal: Bone20090101

Title: Simultaneous determination of 18alpha- and 18beta-glycyrrhetic acid in human plasma by LC-ESI-MS and its application to pharmacokinetics.

Journal: Biomedical chromatography : BMC20090101

Title: Regulatory effects of myoendothelial gap junction on vascular reactivity after hemorrhagic shock in rats.

Journal: Shock (Augusta, Ga.)20090101

Title: Microbial transformation of 18beta-glycyrrhetinic acid by Cunninghamella elegans and Fusarium lini, and lipoxygenase inhibitory activity of transformed products.

Journal: Natural product research20090101

Title: 18beta-Glycyrrhetinic acid induces apoptotic cell death in SiHa cells and exhibits a synergistic effect against antibiotic anti-cancer drug toxicity.

Journal: Life sciences20080926

Title: Enhanced spontaneous Ca2+ events in endothelial cells reflect signalling through myoendothelial gap junctions in pressurized mesenteric arteries.

Journal: Cell calcium20080801

Title: Prevention of free fatty acid-induced hepatic lipotoxicity by 18beta-glycyrrhetinic acid through lysosomal and mitochondrial pathways.

Journal: Hepatology (Baltimore, Md.)20080601

Title: Targeting connexin 43 prevents platelet-derived growth factor-BB-induced phenotypic change in porcine coronary artery smooth muscle cells.

Journal: Circulation research20080328

Title: Role of gap junctions and protein kinase A during the development of oocyte maturational competence in Ayu (Plecoglossus altivelis).

Journal: General and comparative endocrinology20080201

Title: Endothelium-derived hyperpolarizing factor in preeclampsia: heterogeneous contribution, mechanisms, and morphological prerequisites.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology20080201

Title: Role of gap junctions in spontaneous activity of the rat bladder.

Journal: American journal of physiology. Renal physiology20071001

Title: Spontaneous electrical and Ca2+ signals in typical and atypical smooth muscle cells and interstitial cell of Cajal-like cells of mouse renal pelvis.

Journal: The Journal of physiology20070915

Title: Blockade of gap junction coupling by glycyrrhetinic acids in guinea pig cochlear artery: a whole-cell voltage- and current-clamp study.

Journal: British journal of pharmacology20070801

Title: Protein kinase C gamma mutations in the C1B domain cause caspase-3-linked apoptosis in lens epithelial cells through gap junctions.

Journal: Experimental eye research20070701

Title: Primary cultures of chick osteocytes retain functional gap junctions between osteocytes and between osteocytes and osteoblasts.

Journal: Microscopy and microanalysis : the official journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada20070401

Title: 18alpha-glycyrrhetinic acid induces phenotypic changes of skeletal muscle cells to enter adipogenesis.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology20070101

Title: The function of connexin 43 on the differentiation of rat bone marrow cells in culture.

Journal: Biomedical research (Tokyo, Japan)20061201

Title: A gap junction blocker inhibits isolated whole bladder activity in normal rats and rats with partial bladder outlet obstruction.

Journal: Biomedical research (Tokyo, Japan)20061001

Title: The role of connexins in the differentiation of NT2 cells in Sertoli-NT2 cell tissue constructs grown in the rotating wall bioreactor.

Journal: Experimental brain research20060401

Title: Protective effect of gap junction uncouplers given during hypoxia against reoxygenation injury in isolated rat hearts.

Journal: American journal of physiology. Heart and circulatory physiology20060201

Title: Role of gap junctional coupling in astrocytic networks in the determination of global ischaemia-induced oxidative stress and hippocampal damage.

Journal: The European journal of neuroscience20060101

Title: Staphylococcus aureus-derived peptidoglycan induces Cx43 expression and functional gap junction intercellular communication in microglia.

Journal: Journal of neurochemistry20051001

Title: Licorice compounds glycyrrhizin and 18beta-glycyrrhetinic acid are potent modulators of bile acid-induced cytotoxicity in rat hepatocytes.

Journal: The Journal of biological chemistry20050318

Title: Adenoviral delivery of human connexin37 induces endothelial cell death through apoptosis.

Journal: Biochemical and biophysical research communications20040709

Title: Prostaglandin F2alpha amplifies tumor necrosis factor-alpha promoter activity by the FPB prostanoid receptor.

Journal: Biochemical and biophysical research communications20040514

Title: Global, synchronous oscillations in cytosolic calcium and adherence in bradykinin-stimulated Madin-Darby canine kidney cells.

Journal: Acta physiologica Scandinavica20040401

Title: Cytogenetic detection of a trans-species bystander effect: induction of sister chromatid exchanges in murine 3T3 cells by ganciclovir metabolized in HSV thymidine kinase gene-transfected Chinese hamster ovary cells.

Journal: Mutagenesis20040101

Title: Human primary endothelial cells stimulate human osteoprogenitor cell differentiation.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology20040101

Title: [Involvement of gap junctions in stimulation of in vitro maturation of the common frog oocytes by low progesterone concentrations].

Journal: Ontogenez20040101

Title: ECM-induced gap junctional communication enhances mammary epithelial cell differentiation.

Journal: Journal of cell science20030901

Title: Intercellular calcium waves mediate preferential cell growth toward the wound edge in polarized hepatic cells.

Journal: Experimental cell research20030715

Title: Functional hemichannels in astrocytes: a novel mechanism of glutamate release.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience20030501

Title: Expression of connexin 43 mRNA in microisolated murine osteoclasts and regulation of bone resorption in vitro by gap junction inhibitors.

Journal: Biochemical and biophysical research communications20030418

Title: Blockade of brain stem gap junctions increases phrenic burst frequency and reduces phrenic burst synchronization in adult rat.

Journal: Journal of neurophysiology20030101

Title: Inhibitors of gap junctions attenuate myogenic tone in cerebral arteries.

Journal: American journal of physiology. Heart and circulatory physiology20021201

Title: Bone morphogenetic protein-2 modulation of chondrogenic differentiation in vitro involves gap junction-mediated intercellular communication.

Journal: Journal of cellular physiology20021101

Title: The role of gap junctions in mediating endothelium-dependent responses to bradykinin in myometrial small arteries isolated from pregnant women.

Journal: British journal of pharmacology20020801

Title: Critical role of gap junctions in endothelium-dependent hyperpolarization in rat mesenteric arteries.

Journal: Clinical and experimental pharmacology & physiology20020701

Title: Hydrogen peroxide is an endothelium-derived hyperpolarizing factor in human mesenteric arteries.

Journal: Biochemical and biophysical research communications20020125

Title: Bimodal inhibition of connexin 43 gap junctions decreases ACTH-induced steroidogenesis and increases bovine adrenal cell population growth.

Journal: The Journal of endocrinology20011001

Title: An endothelium-derived hyperpolarizing factor-like factor moderates myogenic constriction of mesenteric resistance arteries in the absence of endothelial nitric oxide synthase-derived nitric oxide.

Journal: Hypertension (Dallas, Tex. : 1979)20011001

Title: Dual mechanism of intercellular communication in HOBIT osteoblastic cells: a role for gap-junctional hemichannels.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research20010801

Title: Persistence of gap junction communication during myocardial ischemia.

Journal: American journal of physiology. Heart and circulatory physiology20010601

Title: Endothelium-dependent vasorelaxation independent of nitric oxide and K(+) release in isolated renal arteries of rats.

Journal: British journal of pharmacology20010401

Title: Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.

Journal: Molecular and cellular endocrinology20010122

Title: Blockade of chloride channels reveals relaxations of rat small mesenteric arteries to raised potassium.

Journal: British journal of pharmacology20010101

Title: Zong L et al. 18α-glycyrrhetinic acid extracted from Glycyrrhiza radix inhibits proliferation and promotes apoptosis of the hepatic stellate cell line. J Dig Dis. 2013 Jun;14(6):328-36.

Title: Papaevgeniou N, et al. 18α-Glycyrrhetinic Acid Proteasome Activator Decelerates Aging and Alzheimer's Disease Progression in Caenorhabditis elegans and Neuronal Cultures. Antioxid Redox Signal. 2016 Dec 1;25(16):855-869.

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