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480-11-5 | Oroxylin A
CAS No: 480-11-5 Catalog No: AG003THU MDL No:MFCD02259441
Product Description
Catalog Number:
AG003THU
Chemical Name:
Oroxylin A
CAS Number:
480-11-5
Molecular Formula:
C16H12O5
Molecular Weight:
284.2635
MDL Number:
MFCD02259441
IUPAC Name:
5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one
InChI:
InChI=1S/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-8,18-19H,1H3
InChI Key:
LKOJGSWUMISDOF-UHFFFAOYSA-N
SMILES:
COc1c(O)cc2c(c1O)c(=O)cc(o2)c1ccccc1
UNII:
53K24Z586G
Properties
Complexity:
426
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
284.068g/mol
Formal Charge:
0
Heavy Atom Count:
21
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
284.267g/mol
Monoisotopic Mass:
284.068g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
76A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.1
Literature
| Title | Journal |
|---|---|
| Oroxylin A prevents alcohol-induced hepatic steatosis through inhibition of hypoxia inducible factor 1alpha. | Chemico-biological interactions 20180401 |
| Induction of endothelium-dependent constriction of mesenteric arteries in endotoxemic hypotensive shock. | British journal of pharmacology 20160401 |
| Oroxylin A reverses P-glycoprotein-mediated multidrug resistance of MCF7/ADR cells by G2/M arrest. | Toxicology letters 20130523 |
| Simultaneous determination of baicalin, wogonoside, baicalein, wogonin, oroxylin A and chrysin of Radix scutellariae extract in rat plasma by liquid chromatography tandem mass spectrometry. | Journal of pharmaceutical and biomedical analysis 20121101 |
| Beclin 1-mediated autophagy in hepatocellular carcinoma cells: implication in anticancer efficiency of oroxylin A via inhibition of mTOR signaling. | Cellular signalling 20120801 |
| [Vasodilator effect of oroxylin A on thoracic aorta isolated from rats]. | Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20120801 |
| Activation of the unfolded protein response contributed to the selective cytotoxicity of oroxylin A in human hepatocellular carcinoma HepG2 cells. | Toxicology letters 20120720 |
| The role of Nrf2 and apoptotic signaling pathways in oroxylin A-mediated responses in HCT-116 colorectal adenocarcinoma cells and xenograft tumors. | Anti-cancer drugs 20120701 |
| Detection of baicalin metabolites baicalein and oroxylin-a in mouse pancreas and pancreatic xenografts. | Pancreas 20120501 |
| Oroxylin A analogs exhibited strong inhibitory activities against iNOS-mediated nitric oxide (NO) production. | Bioorganic & medicinal chemistry letters 20120401 |
| Oroxylin A inhibits matrix metalloproteinase-2/9 expression and activation by up-regulating tissue inhibitor of metalloproteinase-2 and suppressing the ERK1/2 signaling pathway. | Toxicology letters 20120325 |
| Oroxylin A reverses CAM-DR of HepG2 cells by suppressing Integrinβ1 and its related pathway. | Toxicology and applied pharmacology 20120315 |
| Comparison of intestinal absorption and disposition of structurally similar bioactive flavones in Radix Scutellariae. | The AAPS journal 20120301 |
| Oroxylin A reverses multi-drug resistance of human hepatoma BEL7402/5-FU cells via downregulation of P-glycoprotein expression by inhibiting NF-κB signaling pathway. | Molecular carcinogenesis 20120201 |
| Synthesis and biological evaluation of 7-O-modified oroxylin A derivatives. | Bioorganic & medicinal chemistry letters 20120115 |
| 4'-bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages. | Bioorganic & medicinal chemistry letters 20120101 |
| STAT1 mediates oroxylin a inhibition of iNOS and pro-inflammatory cytokines expression in microglial BV-2 cells. | PloS one 20120101 |
| Identification and quantification of baicalein, wogonin, oroxylin A and their major glucuronide conjugated metabolites in rat plasma after oral administration of Radix scutellariae product. | Journal of pharmaceutical and biomedical analysis 20110325 |
| Oroxylin A increases BDNF production by activation of MAPK-CREB pathway in rat primary cortical neuronal culture. | Neuroscience research 20110301 |
| Oroxylin A, a flavonoid, stimulates adult neurogenesis in the hippocampal dentate gyrus region of mice. | Neurochemical research 20101101 |
| Synthesis and biological evaluation of novel benzyl-substituted flavones as free radical (DPPH) scavengers and α-glucosidase inhibitors. | Journal of Asian natural products research 20101101 |
| Flavonoids with prolyl oligopeptidase inhibitory activity isolated from Scutellaria racemosa Pers. | Fitoterapia 20100901 |
| Use of isoform-specific UGT metabolism to determine and describe rates and profiles of glucuronidation of wogonin and oroxylin A by human liver and intestinal microsomes. | Pharmaceutical research 20100801 |
| Anti-pruritic effect of baicalin and its metabolites, baicalein and oroxylin A, in mice. | Acta pharmacologica Sinica 20100601 |
| Synergistic effect of 5-fluorouracil and the flavanoid oroxylin A on HepG2 human hepatocellular carcinoma and on H22 transplanted mice. | Cancer chemotherapy and pharmacology 20100201 |
| Involvement of p53 in oroxylin A-induced apoptosis in cancer cells. | Molecular carcinogenesis 20091201 |
| MAC-related mitochondrial pathway in oroxylin-A-induced apoptosis in human hepatocellular carcinoma HepG2 cells. | Cancer letters 20091101 |
| [Flavonoids from Scutellaria baicalensis and their bioactivities]. | Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences 20091018 |
| Evaluation of the flavonoid oroxylin A as an inhibitor of P-glycoprotein-mediated cellular efflux. | Journal of natural products 20090901 |
| Scuteflorins A and B, dihydropyranocoumarins from Scutellaria lateriflora. | Journal of natural products 20090601 |
| Apoptosis induction of oroxylin A in human cervical cancer HeLa cell line in vitro and in vivo. | Toxicology 20090304 |
| Oroxylin A suppresses invasion through down-regulating the expression of matrix metalloproteinase-2/9 in MDA-MB-435 human breast cancer cells. | European journal of pharmacology 20090128 |
| In vitro study of the tocolytic effect of oroxylin A from Scutellaria baicalensis root. | Journal of biomedical science 20090101 |
| Oroxylin A induces G2/M phase cell-cycle arrest via inhibiting Cdk7-mediated expression of Cdc2/p34 in human gastric carcinoma BGC-823 cells. | The Journal of pharmacy and pharmacology 20081101 |
| The effects of acute and repeated oroxylin A treatments on Abeta(25-35)-induced memory impairment in mice. | Neuropharmacology 20081001 |
| Impacts of baicalein analogs with modification of the 6th position of A ring on the activity toward NF-kappaB-, AP-1-, or CREB-mediated transcription. | Bioorganic & medicinal chemistry letters 20080915 |
| [Studies on ethyl acetate soluble constituents of Huanglian Jiedutang]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080901 |
| QSAR modeling of the interaction of flavonoids with GABA(A) receptor. | European journal of medicinal chemistry 20080801 |
| Synthesis and biological evaluation of novel 8-aminomethylated oroxylin A analogues as alpha-glucosidase inhibitors. | Bioorganic & medicinal chemistry letters 20080301 |
| Saireito probably prevents mesangial cell proliferation in HIGA mice via PDGF-BB tyrosine kinase inhibition. | Clinical and experimental nephrology 20071201 |
| New dihydrochalcones and anti-platelet aggregation constituents from the leaves of Muntingia calabura. | Planta medica 20070601 |
| The ameliorating effect of oroxylin A on scopolamine-induced memory impairment in mice. | Neurobiology of learning and memory 20070501 |
| Pharmacokinetics of baicalein, baicalin and wogonin after oral administration of a standardized extract of Scutellaria baicalensis, PF-2405 in rats. | Archives of pharmacal research 20070201 |
| Oroxylin A induced apoptosis of human hepatocellular carcinoma cell line HepG2 was involved in its antitumor activity. | Biochemical and biophysical research communications 20061215 |
| Liquid chromatography with tandem mass spectrometry for the simultaneous determination of baicalein, baicalin, oroxylin A and wogonin in rat plasma. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20061205 |
| Effect of the flavonoid, oroxylin A, on transient cerebral hypoperfusion-induced memory impairment in mice. | Pharmacology, biochemistry, and behavior 20061101 |
| Antioxidative and anti-inflammatory activities of polyhydroxyflavonoids of Scutellaria baicalensis GEORGI. | Bioscience, biotechnology, and biochemistry 20061001 |
| Synthesis and in vitro study of novel 7-O-acyl derivatives of Oroxylin A as antibacterial agents. | Bioorganic & medicinal chemistry letters 20050901 |
| Isolation and purification of baicalein, wogonin and oroxylin A from the medicinal plant Scutellaria baicalensis by high-speed counter-current chromatography. | Journal of chromatography. A 20050513 |
| 5,7-Dihydroxy-6-methoxyflavone, a benzodiazepine site ligand isolated from Scutellaria baicalensis Georgi, with selective antagonistic properties. | Biochemical pharmacology 20030701 |
| Insect antifeedant activity of flavones and chromones against Spodoptera litura. | Journal of agricultural and food chemistry 20030115 |
| Antiviral Chinese medicinal herbs against respiratory syncytial virus. | Journal of ethnopharmacology 20020201 |
| Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana. | Journal of ethnopharmacology 19920401 |
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