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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
Effect of oral micronized purified flavonoid fraction treatment on leukocyte adhesion molecule expression in patients with chronic venous disease: a pilot study.
2000 Mar
New constituents and antiplatelet aggregation and anti-HIV principles of Artemisia capillaris.
2001 Jan
Kaempferol, isorhamnetin and their glycosides in the flowers of Asclepias syriaca L.
2001 Jul-Aug
Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts.
2001 Nov 1
The impact of different flavonoid classes on colonic CI- secretion in rats.
2001 Oct 15
Simultaneous determination of terpene lactones and flavonoid aglycones in Ginkgo biloba by high-performance liquid chromatography with evaporative light scattering detection.
2002 Aug 22
Polyphenolic compounds from the leaves of Koelreuteria paniculata Laxm.
2002 Dec
Effect of five flavonoid compounds isolated from leaves of Diospyros kaki on stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils.
2002 Dec
Endothelium-independent vasodilator effects of the flavonoid quercetin and its methylated metabolites in rat conductance and resistance arteries.
2002 Jul
Characterisation of new oligoglycosidic compounds in two Chinese medicinal herbs.
2002 Jul-Aug
A new coumaronochromone from Sophora japonica.
2002 Mar
Flavonoid glycosides from Rhazya orientalis.
2002 Mar
Comparative study on the free flavonoid aglycones in herbs of different species of Polygonum L.
2002 Mar-Apr
Flavonoid intake and breast cancer risk: a case--control study in Greece.
2003 Oct 6
Molecular characterization and functional expression of flavonol 6-hydroxylase.
2004 Dec 13
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
Effect of Ginkgo biloba extract on rat hepatic microsomal CYP1A activity: role of ginkgolides, bilobalide, and flavonols.
2004 Jan
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
Urinary excretion of flavonoids reflects even small changes in the dietary intake of fruits and vegetables.
2004 May
Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity.
2004 Sep 13
Flavonol glucoside profile of southern Italian red onion (Allium cepa L.).
2005 Apr 6
Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2.
2005 Feb 15
[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
Synergistic effects of flavonoids and ascorbate on enhancement in DNA degradation induced by a bleomycin-Fe complex.
2005 Mar
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 UTC 2023
Edited
by admin
on Sat Dec 16 20:05:49 UTC 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 UTC 2023 , Edited by admin on Sat Dec 16 20:05:49 UTC 2023
PRIMARY
RS_ITEM_NUM
1351800
Created by admin on Sat Dec 16 20:05:49 UTC 2023 , Edited by admin on Sat Dec 16 20:05:49 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-545-5
Created by admin on Sat Dec 16 20:05:49 UTC 2023 , Edited by admin on Sat Dec 16 20:05:49 UTC 2023
PRIMARY
WIKIPEDIA
ISORHAMNETIN
Created by admin on Sat Dec 16 20:05:49 UTC 2023 , Edited by admin on Sat Dec 16 20:05:49 UTC 2023
PRIMARY
CHEBI
6052
Created by admin on Sat Dec 16 20:05:49 UTC 2023 , Edited by admin on Sat Dec 16 20:05:49 UTC 2023
PRIMARY
CHEBI
144055
Created by admin on Sat Dec 16 20:05:49 UTC 2023 , Edited by admin on Sat Dec 16 20:05:49 UTC 2023
PRIMARY
FDA UNII
07X3IB4R4Z
Created by admin on Sat Dec 16 20:05:49 UTC 2023 , Edited by admin on Sat Dec 16 20:05:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID10197379
Created by admin on Sat Dec 16 20:05:49 UTC 2023 , Edited by admin on Sat Dec 16 20:05:49 UTC 2023
PRIMARY
CAS
480-19-3
Created by admin on Sat Dec 16 20:05:49 UTC 2023 , Edited by admin on Sat Dec 16 20:05:49 UTC 2023
PRIMARY
Related Record Type Details
LARREA TRIDENTATA WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
PRIMULA VERIS FLOWER
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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