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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 of ISORHAMNETIN

SMILES

COC1=C(O)C=CC(=C1)C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2

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
Molecular Formula C16H12O7
Molecular Weight 316.2623
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Upjohn
78
Sources: DOI: 10.1021/ja02229a015
Curator's Comment: glucoside

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 56.0 nM [IC50]
Inhibitor
8297
 1.3 µM [IC50]
Inhibitor
8297
 17.0 nM [IC50]
Blocker
537
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Basic research
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The role of transthyretin in the transport of thyroid hormone to cerebrospinal fluid and brain.
1992
[The effects of quercetin and isorhamnetin on oxidative modification of VLDL induced by Cu2+].
2001 Jun
Polyphenolic compounds from the leaves of Koelreuteria paniculata Laxm.
2002 Dec
[Studies on chemical constituents of Cuscuta chinensis].
2002 Feb
EGb 761: ginkgo biloba extract, Ginkor.
2003
Chemical characterization and biological effects of Sicilian Opuntia ficus indica (L.) mill. Fruit juice: antioxidant and antiulcerogenic activity.
2003 Aug 13
[Ginkgo flavones in in vitro metabolism and its clinical application].
2003 Dec
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 Dec
Development and validation of a gas chromatographic-mass spectrometric method for simultaneous identification and quantification of marker compounds including bilobalide, ginkgolides and flavonoids in Ginkgo biloba L. extract and pharmaceutical preparations.
2003 Jan 31
Structure-antioxidant efficiency relationships of phenolic compounds and their contribution to the antioxidant activity of sea buckthorn juice.
2003 Jul 16
Flavonol and drimane-type sesquiterpene glycosides of Warburgia stuhlmannii leaves.
2003 Jun
Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages.
2003 Jun 15
Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity.
2003 May
Intracellular metabolism and bioactivity of quercetin and its in vivo metabolites.
2003 May 15
Effects of the flavonoid quercetin and its methylated metabolite isorhamnetin in isolated arteries from spontaneously hypertensive rats.
2003 Nov
Phenols and flavonoids in Aleppo pine needles as bioindicators of air pollution.
2003 Nov-Dec
Specific inhibition of hypoxia-inducible factor (HIF)-1 alpha activation and of vascular endothelial growth factor (VEGF) production by flavonoids.
2003 Oct
Flavonoid intake and breast cancer risk: a case--control study in Greece.
2003 Oct 6
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 Sep 9
Bioactive phenolics from Carthamus lanatus L.
2003 Sep-Oct
Ingestion of quercetin inhibits platelet aggregation and essential components of the collagen-stimulated platelet activation pathway in humans.
2004 Dec
Cytoprotection by neutral fraction of tannat red wine against oxidative stress-induced cell death.
2004 Dec 1
Protective effects of quercetin and its metabolites on H2O2-induced chromosomal damage to WIL2-NS cells.
2004 Feb
Chemical taxonomy of the Xibei tree peony from China by floral pigmentation.
2004 Feb
[Studies on the flavonoid compounds of Rhododendron anthopogonoides].
2004 Jan
Effect of Ginkgo biloba extract on rat hepatic microsomal CYP1A activity: role of ginkgolides, bilobalide, and flavonols.
2004 Jan
[Glucuronidation and in vitro interaction of Ginkgo flavonoids with other drugs].
2004 Jan
Isotamarixen - a new antioxidant and prolyl endopeptidase-inhibiting triterpenoid from Tamarix hispida.
2004 Jan
Estrogenic activities of Ginkgo biloba extracts.
2004 Jan 30
Mechanisms involved in the antiplatelet activity of rutin, a glycoside of the flavonol quercetin, in human platelets.
2004 Jul 14
Structural requirements of flavonoids for increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes.
2004 Jun
Phytochemical analysis of ethyl acetate extract from Astragalus corniculatus Bieb. and brain antihypoxic activity.
2004 Jun
Flavonoid-rich dark chocolate improves endothelial function and increases plasma epicatechin concentrations in healthy adults.
2004 Jun
The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides.
2004 Jun
Structural investigations of flavonol glycosides from sea buckthorn (Hippophaë rhamnoides) pomace by NMR spectroscopy and HPLC-ESI-MS(n).
2004 Jun 30
Urinary excretion of flavonoids reflects even small changes in the dietary intake of fruits and vegetables.
2004 May
The protozoan Tetrahymena as a bioindicator to screen bioactive substances.
2004 Nov
Characterisation of flavonols in broccoli (Brassica oleracea L. var. italica) by liquid chromatography-uV diode-array detection-electrospray ionisation mass spectrometry.
2004 Oct 29
Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity.
2004 Sep 13
High-performance liquid chromatographic determination of selected flavonols in Ginkgo biloba solid oral dosage forms.
2004 Sep 24
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
Antiinflammatory constituents from the roots of Smilax bockii warb.
2005 Apr
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 Apr 1
Induction of cancer cell apoptosis by flavonoids is associated with their ability to inhibit fatty acid synthase activity.
2005 Feb 18
[Applications of two-dimensional liquid chromatography coupled to mass spectrometry for the separation and identification of compounds in ginkgo biloba extracts].
2005 Jan
The influence of Calendulae officinalis flos extracts on cell cultures, and the chromatographic analysis of extracts.
2005 Jun 15
Quercetin metabolism in vital and apoptotic human leukaemia cells.
2005 Mar
Total flavones of Hippophae rhamnoides promotes early restoration of ultimate stress of healing patellar tendon in a rat model.
2005 May
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 May
Simultaneous determination of quercetin, kaempferol and isorhamnetin accumulated human breast cancer cells, by high-performance liquid chromatography.
2005 Sep 1
Patents

Patents

20010002407
14
JP2003504327A
27
JP2011512798A
9
JPH01213294A
1
JPH0272116A
1
JPH06183940A
2
JPH07165551A
2

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
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:05:49 GMT 2023
Edited
by admin
on Sat Dec 16 20:05:49 GMT 2023
Record UNII
07X3IB4R4Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISORHAMNETIN
INCI   USP-RS  
INCI  
Official Name English
3,4',5,7-TETRAHYDROXY-3'-METHOXYFLAVONE
Systematic Name English
3'-O-METHYLQUERCETIN
Common 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
ISORHAMNETIN [INCI]
Common 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
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
RS_ITEM_NUM
1351800
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-545-5
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
WIKIPEDIA
ISORHAMNETIN
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
CHEBI
6052
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
CHEBI
144055
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
FDA UNII
07X3IB4R4Z
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID10197379
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
CAS
480-19-3
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
Related Record Type Details
LARREA TRIDENTATA WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
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PARENT -> CONSTITUENT ALWAYS PRESENT
PEUMUS BOLDUS LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
ARNICA MONTANA FLOWER
PARENT -> CONSTITUENT ALWAYS PRESENT
GINKGO
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
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