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Luteolin 7-O-glucoside

PubChem CID
5280637
Structure
Luteolin 7-O-glucoside_small.png
Luteolin 7-O-glucoside_3D_Structure.png
Molecular Formula
Synonyms
  • Cynaroside
  • Luteoloside
  • 5373-11-5
  • Luteolin 7-glucoside
  • Luteolin-7-glucoside
Molecular Weight
448.4 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Luteolin 7-O-beta-D-glucoside is a glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant and a plant metabolite. It is a beta-D-glucoside, a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a luteolin. It is a conjugate acid of a luteolin 7-O-beta-D-glucoside(1-).
Cynaroside has been reported in Coreopsis lanceolata, Sonchus fruticosus, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Luteolin 7-O-glucoside.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

PEFNSGRTCBGNAN-QNDFHXLGSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

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

2.2 Molecular Formula

C21H20O11
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

26811-41-6

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG ID

2.3.9 Lipid Maps ID (LM_ID)

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 Wikidata

2.3.13 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-
  • cinaroside
  • cynaroside
  • galuteolin
  • luteolin-7-beta-D-glucoside
  • luteolin-7-glucoside
  • luteolin-7-O-beta-D-glucopyranoside
  • luteolin-7-O-glucoside
  • luteolin-7-O-monoglucoside
  • luteoloside
  • nephrocizin
  • nephrocizine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
448.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
11
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
448.10056145 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
448.10056145 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
186 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
32
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
714
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 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Melting Point

256 - 258 °C

3.3 Chemical Classes

3.3.1 Lipids

Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Copyright
Copyright © 2022-2024 Chemical Block, Russia, Leninsky Prospect 47 - Database Compilation Copyright © 2022-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 2
NIST Number
43925
Library
Main library
Total Peaks
259
m/z Top Peak
286
m/z 2nd Highest
60
m/z 3rd Highest
153
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2 of 2
Source of Spectrum
EP-8733-0-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2.2 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

285.0393 100

284.0308 77.96

151.0033 5.43

256.0378 3.47

360.4881 3.40

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2 of 6
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

447.0924 100

285.0398 7.13

284.0295 2.76

239.7738 1.02

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4.2.3 LC-MS

1 of 68
View All
Accession ID
Authors
Plant Biology, The Noble Foundation, Ardmore, OK, US/Dennis Fine, Daniel Wherritt, and Lloyd Sumner
Instrument
Bruker impact HD
Instrument Type
LC-ESI-QTOF
MS Level
MS
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
10 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
324.6 sec
Top 5 Peaks

447.0938 999

448.0966 251

895.1929 249

283.0245 164

893.1776 146

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License
CC BY-NC-SA
2 of 68
View All
Authors
Tohge T, Plant Science Center, RIKEN.
Instrument
UPLC Q-Tof Premier, Waters
Instrument Type
LC-ESI-QTOF
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
5.0 V
Fragmentation Mode
LOW-ENERGY CID
Column Name
ACQUITY UPLC BEH C18 2.1 by 100 mm (Waters, Milford, MA,USA)
Retention Time
9.91 min
Top 5 Peaks

449.1213 999

450.1427 234

447.1109 61

285.056 61

451.0995 50

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License
CC BY-SA

4.2.4 Other MS

1 of 5
View All
Authors
Institute of Bioorganic Chemistry, Polish Academy of Sciences,Poland/Anna Staszków
Instrument
micrOTOF-Q
Instrument Type
ESI-TOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
25 eV
Column Name
Poroshell 120,EC-C18 2.1x100mm,2.7um
Retention Time
308.566 sec
Precursor m/z
447.094
Precursor Adduct
[M-H]-
Top 5 Peaks

285.04 999

286.044 159

412.83 70

287.047 26

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License
CC BY-SA
2 of 5
View All
Authors
Institute of Bioorganic Chemistry, Polish Academy of Sciences,Poland/Anna Staszków
Instrument
micrOTOF-Q
Instrument Type
ESI-TOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15 eV
Column Name
Poroshell 120,EC-C18 2.1x100mm,2.7um
Retention Time
294.633 sec
Precursor m/z
449.109
Precursor Adduct
[M+H]+
Top 5 Peaks

287.055 999

288.059 111

289.062 15

449.105 13

450.111 3

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License
CC BY-SA

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

  • Cytoplasm
  • Extracellular

8.2 Biochemical Reactions

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.

9.1.2 Hazard Classes and Categories

Not Classified

9.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

13.2 Pathways

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

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

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 LIPID MAPS Classification

16.4 KEGG: Lipid

16.5 KEGG: Phytochemical Compounds

16.6 KEGG : Glycosides

16.7 ChemIDplus

16.8 ChEMBL Target Tree

16.9 UN GHS Classification

16.10 NORMAN Suspect List Exchange Classification

16.11 EPA DSSTox Classification

16.12 LOTUS Tree

16.13 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
    2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside
    https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50241242
  2. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  3. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  4. 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/
  5. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. 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)-7-(β-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one
    https://echa.europa.eu/substance-information/-/substanceinfo/100.023.968
    2-(3,4-dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one (EC: 226-365-8)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/3413
  8. 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
  9. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  10. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
    4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-
    https://www.epa.govt.nz/industry-areas/hazardous-substances/guidance-for-importers-and-manufacturers/hazardous-substances-databases/
  11. ChEBI
  12. 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/
  13. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  14. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  15. Japan Chemical Substance Dictionary (Nikkaji)
  16. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  17. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  18. Natural Product Activity and Species Source (NPASS)
  19. MassBank Europe
  20. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  21. Metabolomics Workbench
  22. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-
    http://www.nist.gov/srd/nist1a.cfm
  23. SpectraBase
    LUTEOLIN-7-O-BETA-D-GLUCOPYRANOSIDE
    https://spectrabase.com/spectrum/5ZFcPxphriP
    4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(hexopyranosyloxy)-5-hydroxy-
    https://spectrabase.com/spectrum/DL8TzQPaqUU
  24. Springer Nature
  25. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  26. Wikidata
  27. Wikipedia
  28. PubChem
  29. 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
  30. GHS Classification (UNECE)
  31. 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/
  32. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  33. PATENTSCOPE (WIPO)
  34. NCBI
CONTENTS