ISORHAMNETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O7
Molecular Weight	316.2623
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(O)C=CC(=C1)C2=C(O)C(=O)C3=C(O2)C=C(O)C=C3O

InChI

InChIKey=IZQSVPBOUDKVDZ-UHFFFAOYSA-N

InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28176246 | https://www.ncbi.nlm.nih.gov/pubmed/28322972 | https://www.ncbi.nlm.nih.gov/pubmed/16765054 | https://www.ncbi.nlm.nih.gov/pubmed/25799286

Isorhamnetin, a flavonol aglycone, isolated from the traditional Chinese medicine H. rhamnoides L., was frequently used in traditional medicine to prevent and treat diverse diseases. Isorhamnetin has been shown to play a variety of roles in anti-oxidation, anti-inflammation, anti-tumor, anti-viral, and neurodegenerative injury protection. Isorhamnetin could inhibit the H2O2-induced activation of the intrinsic apoptotic pathway by scavenging free ROS and extracellular signal-regulated kinase 1/2 (ERK1/2) inactivation. In the type 2 diabetic rat model, isorhamnetin was found to be able to inhibit the NF-κB signaling activity, attenuate oxidative stress, and decrease the production of inflammatory mediators. Isorhamnetin can suppress skin cancer, breast cancer, colon cancer and atherosclerosis by inhibiting PI3K/AKT activation. Isorhamnetin shows inhibitory activity toward CYP1B1 expression and function.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A1 32 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 \| https://www.ncbi.nlm.nih.gov/pubmed/28322972	Inhibitor 8504	56.0 nM [IC50]
Cytochrome P450 1A2 73 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 \| https://www.ncbi.nlm.nih.gov/pubmed/28322972	Inhibitor 8504	1.3 µM [IC50]
Cytochrome P450 1B1 4 Target ID: CHEMBL4878 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 \| https://www.ncbi.nlm.nih.gov/pubmed/28322972	Inhibitor 8504	17.0 nM [IC50]
PI3K-Akt signaling pathway 25 Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28176246	Blocker 555

Conditions

Condition	Modality	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 https://www.ncbi.nlm.nih.gov/pubmed/16765054	Preventing	Basic research	Unknown Approved Use Unknown
Cardiac hypertrophy 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28176246	Primary	Preclinical	Unknown Approved Use Unknown
Atherosclerosis 76 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25799286	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Simultaneous determination of quercetin, kaempferol and isorhamnetin accumulated human breast cancer cells, by high-performance liquid chromatography.	2005-09-01	15905060
The influence of Calendulae officinalis flos extracts on cell cultures, and the chromatographic analysis of extracts.	2005-06-15	15925220
Breast cancer resistance protein (Bcrp1/Abcg2) limits net intestinal uptake of quercetin in rats by facilitating apical efflux of glucuronides.	2005-06	15749994
Total flavones of Hippophae rhamnoides promotes early restoration of ultimate stress of healing patellar tendon in a rat model.	2005-05	15823472
Isolation of five types of flavonol from seabuckthorn (Hippophae rhamnoides) and induction of apoptosis by some of the flavonols in human promyelotic leukemia HL-60 cells.	2005-05	15806302
Flavonol glucoside profile of southern Italian red onion (Allium cepa L.).	2005-04-06	15796618
The simultaneous determination of selected flavonol glycosides and aglycones in Ginkgo biloba oral dosage forms by high-performance liquid chromatography-electrospray ionisation-mass spectrometry.	2005-04-01	15797794
Antiinflammatory constituents from the roots of Smilax bockii warb.	2005-04	15918511
Quercetin metabolism in vital and apoptotic human leukaemia cells.	2005-03	15843173
Synergistic effects of flavonoids and ascorbate on enhancement in DNA degradation induced by a bleomycin-Fe complex.	2005-03	15788228
Induction of cancer cell apoptosis by flavonoids is associated with their ability to inhibit fatty acid synthase activity.	2005-02-18	15533929
Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2.	2005-02-15	15670588
Inhibitory activity of isorhamnetin from Persicaria thunbergii on Farnesyl Protein Transferase.	2005-02	15789745
[Applications of two-dimensional liquid chromatography coupled to mass spectrometry for the separation and identification of compounds in ginkgo biloba extracts].	2005-01	15881366
Oleanane triterpenes from Aegiceras corniculatum.	2005-01	15664478
Investigation of the bioavailability of hypericin, pseudohypericin, hyperforin and the flavonoids quercetin and isorhamnetin following single and multiple oral dosing of a hypericum extract containing tablet.	2005	15727160
Molecular characterization and functional expression of flavonol 6-hydroxylase.	2004-12-13	15596008
Cytoprotection by neutral fraction of tannat red wine against oxidative stress-induced cell death.	2004-12-01	15563225
Ingestion of quercetin inhibits platelet aggregation and essential components of the collagen-stimulated platelet activation pathway in humans.	2004-12	15613018
The protozoan Tetrahymena as a bioindicator to screen bioactive substances.	2004-11	15369859
Characterisation of flavonols in broccoli (Brassica oleracea L. var. italica) by liquid chromatography-uV diode-array detection-electrospray ionisation mass spectrometry.	2004-10-29	15553143
High-performance liquid chromatographic determination of selected flavonols in Ginkgo biloba solid oral dosage forms.	2004-09-24	15576009
Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity.	2004-09-13	15292928
Mechanisms involved in the antiplatelet activity of rutin, a glycoside of the flavonol quercetin, in human platelets.	2004-07-14	15237945
Structural investigations of flavonol glycosides from sea buckthorn (Hippophaë rhamnoides) pomace by NMR spectroscopy and HPLC-ESI-MS(n).	2004-06-30	15212446
Structural requirements of flavonoids for increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes.	2004-06	15279724
Phytochemical analysis of ethyl acetate extract from Astragalus corniculatus Bieb. and brain antihypoxic activity.	2004-06	15274758
Flavonoid-rich dark chocolate improves endothelial function and increases plasma epicatechin concentrations in healthy adults.	2004-06	15190043
The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides.	2004-06	15182387
Urinary excretion of flavonoids reflects even small changes in the dietary intake of fruits and vegetables.	2004-05	15159318
Protective effects of quercetin and its metabolites on H2O2-induced chromosomal damage to WIL2-NS cells.	2004-02	14981287
Chemical taxonomy of the Xibei tree peony from China by floral pigmentation.	2004-02	14685820
Estrogenic activities of Ginkgo biloba extracts.	2004-01-30	14706564
[Studies on the flavonoid compounds of Rhododendron anthopogonoides].	2004-01	15709380
Effect of Ginkgo biloba extract on rat hepatic microsomal CYP1A activity: role of ginkgolides, bilobalide, and flavonols.	2004-01	15052306
[Glucuronidation and in vitro interaction of Ginkgo flavonoids with other drugs].	2004-01	14966933
Isotamarixen - a new antioxidant and prolyl endopeptidase-inhibiting triterpenoid from Tamarix hispida.	2004-01	14765296
Phenols and flavonoids in Aleppo pine needles as bioindicators of air pollution.	2003-12-17	14674550
[Ginkgo flavones in in vitro metabolism and its clinical application].	2003-12	15040090
Enhancing effect of lipids and emulsifiers on the accumulation of quercetin metabolites in blood plasma after the short-term ingestion of onion by rats.	2003-12	14730132
Effects of the flavonoid quercetin and its methylated metabolite isorhamnetin in isolated arteries from spontaneously hypertensive rats.	2003-11	14735435
Bioactive phenolics from Carthamus lanatus L.	2003-10-28	14577635
Flavonoid intake and breast cancer risk: a case--control study in Greece.	2003-10-06	14520456
Specific inhibition of hypoxia-inducible factor (HIF)-1 alpha activation and of vascular endothelial growth factor (VEGF) production by flavonoids.	2003-10	14519939
Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.	2003-09-09	12972054
Chemical characterization and biological effects of Sicilian Opuntia ficus indica (L.) mill. Fruit juice: antioxidant and antiulcerogenic activity.	2003-08-13	12903943
Structure-antioxidant efficiency relationships of phenolic compounds and their contribution to the antioxidant activity of sea buckthorn juice.	2003-07-16	12848490
Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages.	2003-06-15	12787887
[Studies on chemical constituents of Cuscuta chinensis].	2002-02	12774382
The role of transthyretin in the transport of thyroid hormone to cerebrospinal fluid and brain.	1992	1519447

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 100 mg/kg/day for 8 weeks

Route of Administration: Oral

In Vitro Use Guide

Isorhamnetin (3-O-methyl quercetin) had no effect on human neuroblastoma SH-SY5Y cells viability even at 100 uM and even in presence of 500 uM ascorbic acid

Name

Type

Language

ISORHAMNETIN

Official Name

English

3'-O-METHYLQUERCETIN

Preferred Name

English

3,4',5,7-TETRAHYDROXY-3'-METHOXYFLAVONE

Systematic Name

English

METHYLQUERCETIN, 3'-O-

Common Name

English

ISORHAMNETIN (CONSTITUENT OF GINKGO) [DSC]

Common Name

English

ISORHAMNETIN [USP-RS]

Common Name

English

3,5,7-TRIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-4-BENZOPYRONE

Systematic Name

English

FLAVONE, 3,4',5,7-TETRAHYDROXY-3'-METHOXY-

Systematic Name

English

4H-1-BENZOPYRAN-4-ONE, 3,5,7-TRIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-

Systematic Name

English

C.I. 75680

Common Name

English

QUERCETIN 3'-METHYL ETHER

Common Name

English

Code System Code Type Description

PUBCHEM

5281654