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4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl beta-D-glucopyranosiduronic acid

PubChem CID
45782816
Structure
4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl beta-D-glucopyranosiduronic acid_small.png
4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl beta-D-glucopyranosiduronic acid_3D_Structure.png
Molecular Formula
Synonyms
  • 245084-07-5
  • Genistein 4'-O-glucuronide
  • GENISTEIN 4'-BETA-D-GLUCURONIDE
  • (2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxochromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
  • 4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl beta-D-glucopyranosiduronic acid
Molecular Weight
446.4 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2010-06-21
  • Modify:
    2025-02-01
Description
Genistein 4'-O-glucuronide is an acrovestone and an isoflavonoid.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl beta-D-glucopyranosiduronic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxochromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C21H18O11/c22-9-5-12(23)14-13(6-9)30-7-11(15(14)24)8-1-3-10(4-2-8)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21-23,25-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

NHEBJNCJBWUPCK-ZFORQUDYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H18O11
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

245084-07-5

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 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
446.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
6
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
446.08491139 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
446.08491139 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
183 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
746
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)

5 Chemical Vendors

6 Pharmacology and Biochemistry

6.1 Human Metabolite Information

6.1.1 Tissue Locations

  • Kidney
  • Liver

6.1.2 Cellular Locations

  • Cytoplasm
  • Extracellular

7 Safety and Hazards

7.1 Hazards Identification

7.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes

P264, P270, P301+P317, P330, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

7.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

8 Literature

8.1 Consolidated References

8.2 Chemical Co-Occurrences in Literature

8.3 Chemical-Gene Co-Occurrences in Literature

8.4 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

10 Biological Test Results

10.1 BioAssay Results

11 Classification

11.1 ChEBI Ontology

11.2 UN GHS Classification

11.3 EPA DSSTox Classification

11.4 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. ChEBI
  2. 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
  3. EPA DSSTox
    4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl beta-D-glucopyranosiduronic acid
    https://comptox.epa.gov/dashboard/DTXSID00671254
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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
    4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl β-D-Glucopyranosiduronic Acid
    https://echa.europa.eu/substance-information/-/substanceinfo/100.232.478
    4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl β-D-Glucopyranosiduronic Acid (EC: 805-623-9)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/239092
  5. 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
  6. 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
  7. Japan Chemical Substance Dictionary (Nikkaji)
  8. Metabolomics Workbench
  9. Wikidata
    (2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxochromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
    https://www.wikidata.org/wiki/Q76616154
  10. PubChem
  11. GHS Classification (UNECE)
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS