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550-24-3 | Embelin
CAS No: 550-24-3 Catalog No: AG003FYN MDL No:MFCD00016369
Product Description
Catalog Number:
AG003FYN
Chemical Name:
Embelin
CAS Number:
550-24-3
Molecular Formula:
C17H26O4
Molecular Weight:
294.3859
MDL Number:
MFCD00016369
IUPAC Name:
2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
InChI:
InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3
InChI Key:
IRSFLDGTOHBADP-UHFFFAOYSA-N
SMILES:
CCCCCCCCCCCC1=C(O)C(=O)C=C(C1=O)O
EC Number:
208-979-8
UNII:
SHC6U8F5ER
NSC Number:
91874
Properties
Complexity:
432
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
294.183g/mol
Formal Charge:
0
Heavy Atom Count:
21
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
294.391g/mol
Monoisotopic Mass:
294.183g/mol
Rotatable Bond Count:
10
Topological Polar Surface Area:
74.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.4
Literature
| Title | Journal |
|---|---|
| XIAP inhibitor embelin induces autophagic and apoptotic cell death in human oral squamous cell carcinoma cells. | Environmental toxicology 20171101 |
| Discovery of novel second mitochondria-derived activator of caspase mimetics as selective inhibitor of apoptosis protein inhibitors. | The Journal of pharmacology and experimental therapeutics 20140501 |
| Embelin suppresses growth of human pancreatic cancer xenografts, and pancreatic cancer cells isolated from KrasG12D mice by inhibiting Akt and Sonic hedgehog pathways. | PloS one 20140101 |
| Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. | Bioorganic & medicinal chemistry 20121115 |
| Antioxidant activity and protection of pancreatic β-cells by embelin in streptozotocin-induced diabetes. | Journal of diabetes 20120901 |
| Combination therapy of antiandrogen and XIAP inhibitor for treating advanced prostate cancer. | Pharmaceutical research 20120801 |
| Inhibition of UVB-induced oxidative damage and apoptotic biochemical changes in human lymphocytes by 2,5-dihydroxy-3-undecyl-1,4-benzoquinone (embelin). | International journal of radiation biology 20120801 |
| PEG-derivatized embelin as a dual functional carrier for the delivery of paclitaxel. | Bioconjugate chemistry 20120718 |
| XIAP inhibition and generation of reactive oxygen species enhances TRAIL sensitivity in inflammatory breast cancer cells. | Molecular cancer therapeutics 20120701 |
| Co-expression of XIAP and cyclin D1 complex correlates with a poor prognosis in patients with hepatocellular carcinoma. | The American journal of pathology 20120501 |
| Preventive effect of embelin from embelia ribes on lipid metabolism and oxidative stress in high-fat diet-induced obesity in rats. | Planta medica 20120501 |
| Inhibition of X-linked inhibitor of apoptosis with embelin differentially affects male versus female behavioral outcome following neonatal hypoxia-ischemia in rats. | Developmental neuroscience 20120301 |
| Embelin induces apoptosis through down-regulation of XIAP in human leukemia cells. | Medical oncology (Northwood, London, England) 20111201 |
| Protective effect of embelin from Embelia ribes Burm. against transient global ischemia-induced brain damage in rats. | Neurotoxicity research 20111101 |
| Embelin suppresses STAT3 signaling, proliferation, and survival of multiple myeloma via the protein tyrosine phosphatase PTEN. | Cancer letters 20110901 |
| Embelin reduces cutaneous TNF-α level and ameliorates skin edema in acute and chronic model of skin inflammation in mice. | European journal of pharmacology 20110715 |
| Embelin ameliorates dextran sodium sulfate-induced colitis in mice. | International immunopharmacology 20110601 |
| RP-HPLC-DAD method for the estimation of embelin as marker in Embelia ribes and its polyherbal formulations. | Biomedical chromatography : BMC 20110501 |
| Protective effect of embelin against acetic acid induced ulcerative colitis in rats. | European journal of pharmacology 20110301 |
| Anticonvulsant activity of embelin isolated from Embelia ribes. | Phytomedicine : international journal of phytotherapy and phytopharmacology 20110115 |
| Synthesis and evaluation of analgesic and anti-inflammatory activities of most active free radical scavenging derivatives of embelin-A structure-activity relationship. | Chemical & pharmaceutical bulletin 20110101 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| Synthesis and characterization of amphiphilic lipopolymers for micellar drug delivery. | Biomacromolecules 20101011 |
| Prognostic significance of XIAP expression in DLBCL and effect of its inhibition on AKT signalling. | The Journal of pathology 20101001 |
| Embelin suppresses osteoclastogenesis induced by receptor activator of NF-κB ligand and tumor cells in vitro through inhibition of the NF-κB cell signaling pathway. | Molecular cancer research : MCR 20101001 |
| Activation of endothelial nitric oxide synthase by the pro-apoptotic drug embelin: Striking discrepancy between nitric oxide-mediated cyclic GMP accumulation and L-citrulline formation. | Nitric oxide : biology and chemistry 20100515 |
| X-linked inhibitor of apoptosis protein inhibits apoptosis in inflammatory breast cancer cells with acquired resistance to an ErbB1/2 tyrosine kinase inhibitor. | Molecular cancer therapeutics 20100501 |
| Lysosomal destabilization and cathepsin B contributes for cytochrome c release and caspase activation in embelin-induced apoptosis. | Molecular carcinogenesis 20100401 |
| XIAP-mediated protection of H460 lung cancer cells against cisplatin. | European journal of pharmacology 20100210 |
| Chemopreventive and hepatoprotective effects of embelin on N-nitrosodiethylamine and carbon tetrachloride induced preneoplasia and toxicity in rat liver. | Asian Pacific journal of cancer prevention : APJCP 20100101 |
| The XIAP inhibitor Embelin enhances TRAIL-mediated apoptosis in malignant glioma cells by down-regulation of the short isoform of FLIP. | Neurochemistry international 20091101 |
| Effects of embelin on lipid peroxidation and free radical scavenging activity against liver damage in rats. | Basic & clinical pharmacology & toxicology 20091001 |
| Micellar delivery of bicalutamide and embelin for treating prostate cancer. | Pharmaceutical research 20090901 |
| Peroxisome proliferator-activated receptor-gamma contributes to the inhibitory effects of Embelin on colon carcinogenesis. | Cancer research 20090601 |
| Inhibitory effects of antrodins A-E from Antrodia cinnamomea and their metabolites on hepatitis C virus protease. | Phytotherapy research : PTR 20090401 |
| Triterpenes from Cynomorium songaricium--analysis of HCV protease inhibitory activity, quantification, and content change under the influence of heating. | Journal of natural medicines 20090101 |
| Cell-penetrating peptide-conjugated XIAP-inhibitory cyclic hexapeptides enter into Jurkat cells and inhibit cell proliferation. | The FEBS journal 20081201 |
| Activity of 1,4-benzoquinones against formosan subterranean termites (Coptotermes formosanus). | Journal of agricultural and food chemistry 20080611 |
| Protein-protein recognition as a first step towards the inhibition of XIAP and Survivin anti-apoptotic proteins. | Journal of molecular recognition : JMR 20080101 |
| Effect of the XIAP inhibitor Embelin on TRAIL-induced apoptosis of pancreatic cancer cells. | The Journal of surgical research 20071001 |
| Free radical scavenging reactions and antioxidant activity of embelin: biochemical and pulse radiolytic studies. | Chemico-biological interactions 20070425 |
| Wound healing activity of embelin isolated from the ethanol extract of leaves of Embelia ribes Burm. | Journal of ethnopharmacology 20070212 |
| Microwave-assisted extraction of embelin from Embelia ribes. | Biotechnology letters 20070201 |
| Embelin, an inhibitor of X chromosome-linked inhibitor-of-apoptosis protein, blocks nuclear factor-kappaB (NF-kappaB) signaling pathway leading to suppression of NF-kappaB-regulated antiapoptotic and metastatic gene products. | Molecular pharmacology 20070101 |
| Design, synthesis, and characterization of new embelin derivatives as potent inhibitors of X-linked inhibitor of apoptosis protein. | Bioorganic & medicinal chemistry letters 20061115 |
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | Journal of molecular graphics & modelling 20061101 |
| A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes. | Journal of natural products 20061101 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Effects of administration of Embelin and Curcumin on lipid peroxidation, hepatic glutathione antioxidant defense and hematopoietic system during N-nitrosodiethylamine/Phenobarbital-induced hepatocarcinogenesis in Wistar rats. | Molecular and cellular biochemistry 20060301 |
| Cell death in pancreatitis: caspases protect from necrotizing pancreatitis. | The Journal of biological chemistry 20060210 |
| Embelin derivatives and their anticancer activity through microtubule disassembly. | Planta medica 20051001 |
| Chemopreventive effects of embelin and curcumin against N-nitrosodiethylamine/phenobarbital-induced hepatocarcinogenesis in Wistar rats. | Fitoterapia 20050901 |
| Cytotoxic activity of embelin from Lysimachia punctata. | Fitoterapia 20050601 |
| Anti-fertility effects of embelin in female Sprague-Dawley rats may be due to suppression of ovarian function. | Acta biologica Hungarica 20050101 |
| Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XIAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database. | Journal of medicinal chemistry 20040506 |
| Bioactive alkyl phenols and embelin from Oxalis erythrorhiza. | Journal of ethnopharmacology 20031001 |
| Electrochemically synthesized polymer of the plant substance embelin (2,5-dihydroxy-3-undecyl-1,4-benzoquinone). | Applied biochemistry and biotechnology 20010101 |
| Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease. | Phytotherapy research : PTR 20001101 |
| Steroid hormone activity of flavonoids and related compounds. | Breast cancer research and treatment 20000701 |
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