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Isoquercitrin

PubChem CID
5484006
Structure
Isoquercitrin_small.png
Isoquercitrin_3D_Structure.png
Molecular Formula
Synonyms
  • 21637-25-2
  • Isotrifolin
  • Isoquercitroside
  • 3-(((2S,3R,4R,5R)-5-((R)-1,2-Dihydroxyethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
  • 0YX10VRV6J
Molecular Weight
464.4 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-04
Description
Quercetin 3-O-beta-D-glucofuranoside is a quercetin O-glucoside in which a glucofuranosyl residue is attached at position 3 of quercetin via a beta-glycosidic linkage. It has a role as a metabolite. It is a beta-D-glucoside, a quercetin O-glucoside, a monosaccharide derivative and a tetrahydroxyflavone.
Isoquercitrin is under investigation in clinical trial NCT04622865 (Masitinib Combined With Isoquercetin and Best Supportive Care in Hospitalized Patients With Moderate and Severe COVID-19).
3-(((2S,3R,4R,5R)-5-((R)-1,2-Dihydroxyethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one has been reported in Camellia sinensis, Caragana spinosa, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Isoquercitrin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[(2S,3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C21H20O12/c22-6-12(27)19-16(29)17(30)21(32-19)33-20-15(28)14-11(26)4-8(23)5-13(14)31-18(20)7-1-2-9(24)10(25)3-7/h1-5,12,16-17,19,21-27,29-30H,6H2/t12-,16-,17-,19-,21+/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

OPJZLUXFQFQYAI-GNPVFZCLSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@H](O4)[C@@H](CO)O)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H20O12
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 DrugBank ID

2.3.6 DSSTox Substance ID

2.3.7 Metabolomics Workbench ID

2.3.8 NCI Thesaurus Code

2.3.9 Nikkaji Number

2.3.10 Pharos Ligand ID

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
  • 4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy
  • flavone, 3,3',4',5,7-pentahydroxy-, 3-beta-D-glucofuranoside
  • isoquercetin
  • isoquercitin
  • isoquercitrin
  • isoquercitroside
  • isotrifoliin
  • quercetin 3-(beta-D-glucofuranoside)
  • quercetin 3-O-beta-D-glucofuranoside
  • quercetin-3-glucoside
  • quercetin-3-O-beta-glucoside
  • quercetin-3-O-glucoside
  • trifoliin
  • trifoliin A

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
464.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
0.4
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
464.09547607 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
464.09547607 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
207Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
33
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
758
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
5
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Cosmetics

Antioxidant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

5 Chemical Vendors

6 Pharmacology and Biochemistry

6.1 Biochemical Reactions

7 Use and Manufacturing

7.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125

7.1.1 Use Classification

Cosmetics -> Antioxidant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports. Pictograms displayed are for < 0.1% (0 of 2) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 2 of 2 companies. For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 2 of 2 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 0 notifications provided by 0 of 2 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

8.1.2 Hazard Classes and Categories

Not Classified

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 Chemical Co-Occurrences in Patents

10.3 Chemical-Disease Co-Occurrences in Patents

10.4 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Pathways

12 Biological Test Results

12.1 BioAssay Results

13 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

14 Classification

14.1 MeSH Tree

14.2 NCI Thesaurus Tree

14.3 ChEBI Ontology

14.4 ChemIDplus

14.5 UN GHS Classification

14.6 EPA CPDat Classification

14.7 NORMAN Suspect List Exchange Classification

14.8 EPA DSSTox Classification

14.9 LOTUS Tree

14.10 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    2-(3,4-dihydroxyphenyl)-3-(β-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
    https://echa.europa.eu/substance-information/-/substanceinfo/100.040.429
    2-(3,4-dihydroxyphenyl)-3-(β-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one (EC: 244-488-5)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/120990
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. ChEBI
  8. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    3-(((2S,3R,4R,5R)-5-((R)-1,2-Dihydroxyethyl)-3,4-dihydroxytetrahydrofuran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
    https://www.wikidata.org/wiki/Q27103621
  9. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  10. EPA Chemical and Products Database (CPDat)
  11. Japan Chemical Substance Dictionary (Nikkaji)
  12. Metabolomics Workbench
  13. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  14. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  15. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  16. Wikidata
  17. PubChem
  18. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  19. GHS Classification (UNECE)
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS