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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O12
Molecular Weight 464.3763
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOQUERCETIN

SMILES

OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C4=CC=C(O)C(O)=C4)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=OVSQVDMCBVZWGM-QSOFNFLRSA-N
InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H20O12
Molecular Weight 464.3763
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Isoquercetin is a flavonoid, derivative of quercetin. It was isolated from various plant species including Ammothamnus Lehmanii, Caragana alaica, Cicer baldshuanicum, C. macroconthum, C. pungens, Euphorbia cyparissias, E. helioscapia, E. lathyris, E. lucida, E. purporata and others. It demonstrated radical scavenging activity, inhibitory effects on Na+/K+-ATPase and positive inotropic activity. It is protein disulfide isomerase (PDI) inhibitor. As a PDI inhibitor, this agent blocks PDI-mediated platelet activation, and fibrin generation, which prevents thrombus formation after vascular injury. Isoquercetin inhibited the replication of both influenza A and B viruses at the lowest effective concentration. Isoquercetin activates the ERK1/2-Nrf2 pathway and protects against cerebral ischemia-reperfusion injury in vivo and in vitro. It is being investigated for prevention of thromboembolism in selected cancer patients and as an anti-fatigue agent in kidney cancer patients treated with sunitinib.

Originator

Sources: DOI: 10.1007/978-1-4614-0535-1_485

Approval Year

AUC

AUC

ValueDoseCo-administeredAnalytePopulation
15 μM × h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUERCETIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase.
1995 Apr
A search for anti-viral properties in Panamanian medicinal plants. The effects on HIV and its essential enzymes.
1999 Jan
Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease.
2000 Nov
[HPLC investigation of antioxidant components in Solidago herba].
2004
Isolation of angiotensin converting enzyme (ACE) inhibitory flavonoids from Sedum sarmentosum.
2004 Dec
[Studies on antiproliferative effect of flavones compounds isolated from Yao herb medicines].
2007 Aug
Determination of quercetin and its glucosides in onion by electrochemical methods.
2008 Jun 9
Deconjugation and degradation of flavonol glycosides by pig cecal microbiota characterized by Fluorescence in situ hybridization (FISH).
2008 Mar 26
Camellia japonica suppresses immunoglobulin E-mediated allergic response by the inhibition of Syk kinase activation in mast cells.
2008 May
Light filtering by epidermal flavonoids during the resistant response of cotton to Xanthomonas protects leaf tissue from light-dependent phytoalexin toxicity.
2008 Sep
[Flavones from Helichrysi flos syn].
2009 Jun
Phenolic compounds in leaves of Alchornea triplinervia: anatomical localization, mutagenicity, and antibacterial activity.
2010 Aug
Patents

Sample Use Guides

500 mg or 1000 mg, Once daily, 28 days
Route of Administration: Oral
The protein expression of Nrf2 in rat hippocampal neurons in the 100 ug/ml group increased by 200% compared with the OGD/R (oxygen-glucose deprivation followed by reoxygenation) group.
Substance Class Chemical
Created
by admin
on Thu Jul 06 01:42:26 UTC 2023
Edited
by admin
on Thu Jul 06 01:42:26 UTC 2023
Record UNII
6HN2PC637T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOQUERCETIN
INCI  
Official Name English
QUERCETIN-3-O-.BETA.-D-GLUCOSIDE
Systematic Name English
QUERCETIN 3.BETA.-GLUCOSIDE
Common Name English
ISOQUERCETIN [INCI]
Common Name English
QUERCETIN-3-O-GLUCOSIDE
Common Name English
3',4',5,7-TETRAHYDROXYFLAVONE-3-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-
Common Name English
ISOQUERCITRIN [MI]
Common Name English
NSC-115918
Code English
QUERCETIN-3-.BETA.-GLUCOPYRANOSIDE
Common Name English
QUERCETIN 3-O-GLUCOSIDE
Common Name English
GLUCOSYL-3-QUERCETIN
Common Name English
Quercetin 3-O-glucopyranoside [WHO-DD]
Common Name English
QUERCETIN GLUCOSIDE
Common Name English
3-GLUCOSYLQUERCETIN
Common Name English
QUERCETIN 3-D-GLUCOSIDE
Common Name English
QUERCETIN 3-O-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
3-O-.BETA.-D-GLUCOPYRANOSYLQUERCETIN
Common Name English
QUERCETOL 3-MONOGLUCOSIDE
Common Name English
QUERCETIN 3-O-GLUCOPYRANOSIDE
WHO-DD  
Common Name English
CONTIGOSIDE B
Common Name English
QUERCETIN-3-GLUCOSE
Common Name English
ISOQUERCETIN, (-)-
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2- (3,4-DIHYDROXYPHENYL)-3- (SS-D-GLUCOFURANOSYLOXY)-5,7-DIHYDROXY-
Systematic Name English
QUERCETIN 3-O-GLUCOSIDE (CONSTITUENT OF GINKGO) [DSC]
Common Name English
HIRSUTRIN
Common Name English
RONACARE ISOQUERCETIN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C68457
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
Code System Code Type Description
CHEBI
28299
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
NSC
115918
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
PUBCHEM
5280804
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID3041110
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
FDA UNII
6HN2PC637T
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
MESH
C110309
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
CHEBI
68352
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
CAS
482-35-9
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
NCI_THESAURUS
C117288
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
WIKIPEDIA
ISOQUERCETIN
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
SMS_ID
300000017646
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
MERCK INDEX
M6537
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB12665
Created by admin on Thu Jul 06 01:42:26 UTC 2023 , Edited by admin on Thu Jul 06 01:42:26 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER Flavonoid
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Repeated chromatography of the n-BuOH soluble fraction yielded this flavonoid glucoside. Has shown antimicrobial activiral activity in other studies.
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Secondary metabolite detected in developing cacao seeds.