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Umbelliferone

PubChem CID
5281426
Structure
Umbelliferone_small.png
Umbelliferone_3D_Structure.png
Umbelliferone__Crystal_Structure.png
Molecular Formula
Synonyms
  • Umbelliferone
  • 7-hydroxycoumarin
  • 93-35-6
  • 7-Hydroxy-2H-chromen-2-one
  • Hydrangin
Molecular Weight
162.14 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Umbelliferone is a hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7. It has a role as a fluorescent probe, a plant metabolite and a food component.
Umbelliferone has been reported in Hydrangea serrata, Caragana frutex, and other organisms with data available.
See also: Chamomile (part of).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Umbelliferone.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 2
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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

7-hydroxychromen-2-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C1=CC(=CC2=C1C=CC(=O)O2)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C9H6O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

93-35-6

2.3.2 Deprecated CAS

1391-97-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 NSC Number

2.3.13 Pharos Ligand ID

2.3.14 Wikidata

2.3.15 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 7-hydroxycoumarin
  • 7-hydroxycoumarin sulfate
  • 7-hydroxycoumarin, 14C-labeled
  • umbelliferone

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
162.14 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.6
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
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
162.031694049 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
162.031694049 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
46.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
222
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 Physical Description

Solid; [Merck Index] White or pale yellow powder; [Alfa Aesar MSDS]
Solid

3.2.2 Melting Point

230 - 232 °C

3.2.3 Collision Cross Section

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

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

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

154.46 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

130.56 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

130.1 Ų [M-H]-

153.5 Ų [M+Na]+

S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.2.4 Kovats Retention Index

Standard non-polar
1789 , 1795 , 1797 , 1828
Semi-standard non-polar
1852.5 , 1828 , 1836

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Dyes -> Coumarin Dyes
UV filter
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60D
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
H24003
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
Source of Sample
M. Loutfy, Riyad University, Riyad, Saudi Arabia
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
BRUKER AM-400
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 12
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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

162.0 99.99

134.0 91

78.0 42.30

51.0 33.30

105.0 28.20

Thumbnail
Thumbnail
Notes
instrument=HITACHI RMU-7L
2 of 12
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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

162.0 99.99

78.0 21.70

105.0 18.60

77.0 13.20

67.0 10.20

Thumbnail
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Notes
instrument=HITACHI RMU-6E

4.2.2 MS-MS

1 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

163.0392 100

107.0493 31.18

119.0493 17.45

164.0425 11.12

135.0444 3.95

Thumbnail
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2 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

163.0392 100

164.0425 10.22

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4.2.3 LC-MS

1 of 38
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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
236.4 sec
Top 5 Peaks

161.0246 999

162.0276 72

700.0316 35

133.0296 18

701.035 13

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 38
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
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
20 eV
Column Name
Waters Acquity BEH C18 1.7um x 2.1 x 150 mm
Retention Time
235.8 sec
Precursor m/z
161.0247
Precursor Adduct
[M-H]-
Top 5 Peaks

161.0247 999

133.0297 607

117.035 85

162.0279 57

134.0324 31

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License
CC BY-NC-SA

4.2.4 Other MS

1 of 5
View All
Authors
NAKAYAMA M, MASS SPECTROSCOPY SOC. OF JAPAN (MSSJ)
Instrument
HITACHI RMU-7L
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

162 999

134 910

78 423

51 333

105 282

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 5
View All
Authors
YAMAMOTO M, DEP. CHEMISTRY, FAC. SCIENCE, NARA WOMEN'S UNIV.
Instrument
HITACHI RMU-6E
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

162 999

78 217

105 186

77 132

67 102

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.3 UV Spectra

4.3.1 UV-VIS Spectra

1 of 2
Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Fluka Chemie AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Technique
KBr WAFER
Source of Sample
COLUMBIA ORGANIC CHEMICALS COMPANY, INC., COLUMBIA, SOUTH CAROLINA
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Inc.
Catalog Number
H24003
Lot Number
92997PJV
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
H24003
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company Llc
Catalog Number
<a href=https://www.sigmaaldrich.com/US/en/product/aldrich/H24003>H24003</a>
Lot Number
91997PJV
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Metabolism / Metabolites

7-Hydroxycoumarin is a known human metabolite of 7-ethoxycoumarin, coumarin, and 7-methoxycoumarin.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

8.2 Human Metabolite Information

8.2.1 Cellular Locations

  • Cytoplasm
  • Extracellular

8.3 Biochemical Reactions

8.4 Transformations

9 Use and Manufacturing

9.1 Uses

Sources/Uses
Found in many plants; Used in sunscreens, as intracellular and pH sensitive fluorescent indicator, and blood-brain barrier probe; [Merck Index] Active metabolite of coumarin. [ChemIDplus]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
Synthetic Polymer MALDI Matrix Compounds

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
Pictograms displayed are for 98.8% (163 of 165) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 1.2% (2 of 165) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (98.8%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (98.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (98.2%): 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 165 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 2 of 165 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 7 notifications provided by 163 of 165 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.

10.1.2 Hazard Classes and Categories

Skin Irrit. 2 (98.8%)

Eye Irrit. 2 (98.8%)

STOT SE 3 (98.2%)

10.1.3 Hazards Summary

Causes liver effects, effects on plasma proteins, hypoglycemia, and changes in clotting factors in 45-day intermittent intraperitoneal studies of rats; [RTECS] An irritant; [Alfa Aesar MSDS] See Coumarin.

10.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 2H-1-Benzopyran-2-one, 7-hydroxy-
New Zealand EPA Inventory of Chemical Status
2H-1-Benzopyran-2-one, 7-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Nature Journal References

13.7 Chemical Co-Occurrences in Literature

13.8 Chemical-Gene Co-Occurrences in Literature

13.9 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
S29 | PHYTOTOXINS | Toxic Plant Phytotoxin (TPPT) Database | DOI:10.5281/zenodo.2652993

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 KEGG: Phytochemical Compounds

18.4 ChemIDplus

18.5 ChEMBL Target Tree

18.6 UN GHS Classification

18.7 NORMAN Suspect List Exchange Classification

18.8 CCSBase Classification

18.9 EPA DSSTox Classification

18.10 NIST Synthetic Polymer MALDI Recipes Database Classification

18.11 LOTUS Tree

18.12 EPA Substance Registry Services Tree

18.13 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DTP/NCI
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    https://www.cancer.gov/policies/copyright-reuse
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. 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
  7. 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
  8. Human Metabolome Database (HMDB)
    LICENSE
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    http://www.hmdb.ca/citing
  9. 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/
  10. 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
  11. 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
  12. 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
  13. Therapeutic Target Database (TTD)
  14. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  15. 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/
    7-Hydroxycoumarin
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  16. ChEBI
  17. 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/
  18. 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
  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. 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
  21. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
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    https://haz-map.com/About
  22. NIST Synthetic Polymer MALDI Recipes Database
    LICENSE
    Formerly known as NIST Standard Reference Database 172
    https://www.nist.gov/disclaimer
    7-hydroxycoumarin
    https://maldi.nist.gov/
  23. 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
  24. 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
  25. SpectraBase
    2H-1-BENZOPYRAN-2-ONE, 7-HYDROXY-
    https://spectrabase.com/spectrum/BW7EVFBnj86
  26. Japan Chemical Substance Dictionary (Nikkaji)
  27. 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
  28. KNApSAcK Species-Metabolite Database
  29. Natural Product Activity and Species Source (NPASS)
  30. MassBank Europe
  31. Metabolomics Workbench
  32. Nature Chemical Biology
  33. Nature Chemistry
  34. Nature Synthesis
  35. NMRShiftDB
  36. 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
  37. Protein Data Bank in Europe (PDBe)
  38. 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
  39. Rhea - Annotated Reactions Database
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    https://www.rhea-db.org/help/license-disclaimer
  40. Springer Nature
  41. SpringerMaterials
  42. The Cambridge Structural Database
  43. Thieme Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc-nd/4.0/
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  46. Wiley
  47. PubChem
  48. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  49. GHS Classification (UNECE)
  50. EPA Substance Registry Services
  51. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  52. PATENTSCOPE (WIPO)
  53. NCBI
CONTENTS