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Baicalein

PubChem CID
5281605
Structure
Baicalein_small.png
Baicalein_3D_Structure.png
Baicalein__Crystal_Structure.png
Molecular Formula
Synonyms
  • baicalein
  • 491-67-8
  • 5,6,7-Trihydroxyflavone
  • Noroxylin
  • 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one
Molecular Weight
270.24 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Baicalein is a trihydroxyflavone with the hydroxy groups at positions C-5, -6 and -7. It has a role as an antioxidant, a hormone antagonist, a prostaglandin antagonist, an EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a radical scavenger, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an anti-inflammatory agent, a plant metabolite, a ferroptosis inhibitor, an anticoronaviral agent, an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, an angiogenesis inhibitor, an antineoplastic agent, an EC 4.1.1.17 (ornithine decarboxylase) inhibitor, an antibacterial agent, an antifungal agent, an apoptosis inducer and a geroprotector. It is a conjugate acid of a baicalein(1-).
Baicalein is under investigation in clinical trial NCT03830684 (A Randomized, Double-blind, Placebo-controlled, Multicenter and Phase ⅡA Clinical Trial for the Effectiveness and Safety of Baicalein Tablets in the Treatment of Improve Other Aspects of Healthy Adult With Influenza Fever).
Baicalein has been reported in Lepisorus ussuriensis, Scutellaria prostrata, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Baicalein.png

1.2 3D Conformer

1.3 Crystal Structures

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CCDC Number
Associated Article
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5,6,7-trihydroxy-2-phenylchromen-4-one
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

FXNFHKRTJBSTCS-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H10O5
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 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 KEGG ID

2.3.9 Lipid Maps ID (LM_ID)

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 NSC Number

2.3.14 Pharos Ligand ID

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

baicalein

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
270.24 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
1.7
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
270.05282342 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
270.05282342 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
87 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
412
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
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 Collision Cross Section

153.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

167.9 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

153.12 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

182.55 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

149.4 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

3.3 Chemical Classes

3.3.1 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

3.3.2 Lipids

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

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
465119
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 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 © 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 2
Source of Spectrum
CD-312-0-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
G4-61-1414-2
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2.2 MS-MS

1 of 2
NIST Number
1118598
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M-H]-
Precursor m/z
269.0455
Total Peaks
44
m/z Top Peak
251.1
m/z 2nd Highest
241.1
m/z 3rd Highest
223.1
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2 of 2
NIST Number
1118599
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
271.0601
Total Peaks
33
m/z Top Peak
253.1
m/z 2nd Highest
271
m/z 3rd Highest
225.1
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4.2.3 LC-MS

1 of 29
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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
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
40 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
685.8 sec
Precursor m/z
269.0452
Precursor Adduct
[M-H]-
Top 5 Peaks

137.0073 999

139.0234 365

111.0094 237

171.0668 225

223.0479 225

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License
CC BY-NC-SA
2 of 29
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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
685.8 sec
Top 5 Peaks

267.0305 999

269.0459 860

239.0351 126

268.0334 122

270.0491 109

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License
CC BY-NC-SA

4.2.4 Other MS

1 of 5
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Authors
CASMI2013 organizers
Instrument
LC-IT-TOF (Shimadzu)
Instrument Type
ESI-ITTOF
MS Level
MS
Ionization Mode
NEGATIVE
Ionization
ESI
Top 5 Peaks

269.0449 999

270.0397 87

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License
CC BY-SA
2 of 5
View All
Authors
CASMI2013 organizers
Instrument
LC-IT-TOF (Shimadzu)
Instrument Type
ESI-ITTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
80 % by Ar 50 %
Precursor m/z
269.04445
Precursor Adduct
[M-H]-
Top 5 Peaks

251.0347 999

241.0529 441

223.0396 193

252.0391 152

169.0675 82

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License
CC BY-SA

4.3 IR Spectra

4.3.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Indofine Chemical Company, Inc.
Catalog Number
B-101
Lot Number
40212
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Indofine Chemical Company, Inc.
Catalog Number
B-101
Lot Number
040212
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

7.2 Clinical Trials

7.2.1 ClinicalTrials.gov

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

Antioxidants
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)
Enzyme Inhibitors
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)
Prostaglandin Antagonists
Compounds that inhibit the action of prostaglandins. (See all compounds classified as Prostaglandin Antagonists.)

9.2 Biochemical Reactions

10 Use and Manufacturing

10.1 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

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (95.8%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (95.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (93.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

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

ECHA C&L Notifications Summary

Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

11.1.2 Hazard Classes and Categories

Skin Irrit. 2 (95.8%)

Eye Irrit. 2 (95.8%)

STOT SE 3 (93.8%)

11.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Baicalein: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Nature Journal References

13.5 Chemical Co-Occurrences in Literature

13.6 Chemical-Gene Co-Occurrences in Literature

13.7 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15.2 Chemical-Target Interactions

15.3 Pathways

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

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

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 LIPID MAPS Classification

18.4 KEGG: Lipid

18.5 KEGG: Phytochemical Compounds

18.6 ChemIDplus

18.7 ChEMBL Target Tree

18.8 UN GHS Classification

18.9 EPA CPDat Classification

18.10 NORMAN Suspect List Exchange Classification

18.11 CCSBase Classification

18.12 EPA DSSTox Classification

18.13 LOTUS Tree

18.14 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. BindingDB
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    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. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  3. Therapeutic Target Database (TTD)
  4. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  5. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  6. DrugBank
    LICENSE
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    https://www.drugbank.ca/legal/terms_of_use
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    https://www.cancer.gov/policies/copyright-reuse
  8. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  9. 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
  10. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  11. 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/
  12. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  13. ChEBI
  14. 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/
  15. NCI Thesaurus (NCIt)
    LICENSE
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    https://www.cancer.gov/policies/copyright-reuse
  16. Open Targets
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    https://platform-docs.opentargets.org/licence
  17. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  18. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  19. 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/
  20. The Cambridge Structural Database
  21. EPA Chemical and Products Database (CPDat)
  22. 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
  23. Japan Chemical Substance Dictionary (Nikkaji)
  24. 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
  25. KNApSAcK Species-Metabolite Database
  26. Natural Product Activity and Species Source (NPASS)
  27. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  28. MassBank Europe
  29. 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
  30. Metabolomics Workbench
  31. Nature Chemical Biology
  32. 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
  33. 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/
  34. 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
  35. Protein Data Bank in Europe (PDBe)
  36. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  37. SpectraBase
  38. Springer Nature
  39. Wikidata
  40. Wikipedia
  41. PubChem
  42. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  43. GHS Classification (UNECE)
  44. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  45. PATENTSCOPE (WIPO)
  46. NCBI
CONTENTS