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Salvigenin

PubChem CID
161271
Structure
Salvigenin_small.png
Salvigenin_3D_Structure.png
Salvigenin__Crystal_Structure.png
Molecular Formula
Synonyms
  • Salvigenin
  • 19103-54-9
  • psathyrotin
  • 5-Hydroxy-6,7,4'-trimethoxyflavone
  • 7-O-methylpectolinarigenin
Molecular Weight
328.3 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-28
  • Modify:
    2024-12-28
Description
Salvigenin is a trimethoxyflavone that is scutellarein in which the hydroxy groups at positions 4', 6, and 7 are replaced by methoxy groups. It has a role as an autophagy inducer, an apoptosis inhibitor, an antilipemic drug, an immunomodulator, an antineoplastic agent, a neuroprotective agent, a hypoglycemic agent and a plant metabolite. It is a trimethoxyflavone and a monohydroxyflavone. It is functionally related to a scutellarein.
Salvigenin has been reported in Salvia miltiorrhiza, Mesosphaerum urticoides, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Salvigenin.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 3
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-hydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C18H16O6/c1-21-11-6-4-10(5-7-11)13-8-12(19)16-14(24-13)9-15(22-2)18(23-3)17(16)20/h4-9,20H,1-3H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

QCDYOIZVELGOLZ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COC1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)OC)O
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C18H16O6
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 Lipid Maps ID (LM_ID)

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5-hydroxy-6,7,4'-trimethoxy-flavone
  • 5-hydroxy-6,7,4'-trimethoxyflavone
  • salvigenin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
328.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
328.09468823 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
328.09468823 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
74.2Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
482
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
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 Kovats Retention Index

Semi-standard non-polar
3232.6

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Lipids

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

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Instrument Name
Jeol FX-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 4
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NIST Number
414368
Library
Main library
Total Peaks
235
m/z Top Peak
328
m/z 2nd Highest
313
m/z 3rd Highest
153
Thumbnail
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2 of 4
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NIST Number
58228
Library
Replicate library
Total Peaks
20
m/z Top Peak
328
m/z 2nd Highest
313
m/z 3rd Highest
69
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4.2.2 LC-MS

1 of 2
Authors
Toshimitsu HAYASHI, Ken TANAKA
Instrument
LCMS-IT-TOF
Instrument Type
LC-ESI-ITTOF
MS Level
MS
Ionization Mode
POSITIVE
Column Name
Waters Atlantis T3 (2.1 x 150 mm, 5 um)
Retention Time
23.393333 min
Top 5 Peaks

329.0992 999

330.1111 196

351.0897 41

314.0898 37

331.1071 30

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License
CC BY-SA
2 of 2
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS1
Instrument
LCMS-IT-TOF
Instrument Type
LC-ESI-ITTOF
Ionization Mode
positive
Retention Time
23.393333 min
Top 5 Peaks

329.099200 100

330.111100 19.66

351.089700 4.09

314.089800 3.68

331.107100 2.96

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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 Biochemical Reactions

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Thieme References

9.5 Chemical Co-Occurrences in Literature

9.6 Chemical-Gene Co-Occurrences in Literature

9.7 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

10.5 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Chemical-Target Interactions

11.2 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 ChEBI Ontology

14.3 LIPID MAPS Classification

14.4 ChemIDplus

14.5 ChEMBL Target Tree

14.6 EPA DSSTox Classification

14.7 LOTUS Tree

14.8 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. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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
  5. 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
  6. ChEBI
  7. 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/
  8. 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
  9. 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
  10. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  11. The Cambridge Structural Database
  12. 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
  13. Japan Chemical Substance Dictionary (Nikkaji)
  14. KNApSAcK Species-Metabolite Database
  15. Natural Product Activity and Species Source (NPASS)
  16. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  17. MassBank Europe
  18. 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
  19. Metabolomics Workbench
  20. 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, 5-hydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-
    http://www.nist.gov/srd/nist1a.cfm
  21. SpectraBase
    4H-1-Benzopyran-4-one, 5-hydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-
    https://spectrabase.com/spectrum/5aUoatVlkUW
    4H-1-Benzopyran-4-one, 5-hydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-
    https://spectrabase.com/spectrum/95ye3NaajHQ
  22. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  23. Springer Nature
  24. SpringerMaterials
  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. PubChem
  28. 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
  29. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  30. PATENTSCOPE (WIPO)
CONTENTS