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Icosapent

PubChem CID
446284
Structure
Icosapent_small.png
Icosapent_3D_Structure.png
Molecular Formula
Synonyms
  • Eicosapentaenoic acid
  • Timnodonic acid
  • Icosapent
  • 10417-94-4
  • Icosapentaenoic acid
Molecular Weight
302.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11
Description
All-cis-5,8,11,14,17-icosapentaenoic acid is an icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17. It has a role as a nutraceutical, a micronutrient, an antineoplastic agent, an antidepressant, a Daphnia galeata metabolite, a mouse metabolite, an anticholesteremic drug and a fungal metabolite. It is an icosapentaenoic acid and an omega-3 fatty acid. It is a conjugate acid of an all-cis-5,8,11,14,17-icosapentaenoate.
Important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families.
Eicosapentaenoic acid has been reported in Mortierella alpina, Tornabea scutellifera, and other organisms with data available.
See also: Icosapent Ethyl (active moiety of); Fish Oil (is active moiety of); Eicosapentaenoic Acid (subclass of) ... View More ...

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Icosapent.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

JAZBEHYOTPTENJ-JLNKQSITSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C20H30O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

25377-48-4

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 KEGG ID

2.3.11 Lipid Maps ID (LM_ID)

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 PharmGKB ID

2.3.15 RXCUI

2.3.16 Wikidata

2.3.17 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5,8,11,14,17-Eicosapentaenoic Acid
  • 5,8,11,14,17-Icosapentaenoic Acid
  • Acid, Eicosapentanoic
  • Eicosapentaenoic Acid
  • eicosapentanoic acid
  • Icosapent
  • omega 3 Eicosapentaenoic Acid
  • omega-3-Eicosapentaenoic Acid
  • Timnodonic Acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
302.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
5.6
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
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
13
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
302.224580195 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
302.224580195 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
398
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
5
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

Liquid

3.2.2 LogP

6.1

3.2.3 Collision Cross Section

180.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
178.53 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

3.2.4 Kovats Retention Index

Semi-standard non-polar
2334.2 , 2327.7

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.4.1.1 Human Drugs
Paediatric drug

3.4.2 Cosmetics

Emollient; Skin conditioning
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

3.4.3 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

3.4.4 Lipids

Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]

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
277851
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.
Thumbnail
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
277851
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 5
View All
Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

79.0 1

91.0 0.57

117.0 0.33

80.0 0.28

105.0 0.27

Thumbnail
Thumbnail
2 of 5
View All
MS Category
Experimental
MS Type
GC-MS
Instrument Type
GC-MS
Top 5 Peaks

79.0 1

91.0 0.57

117.0 0.33

80.0 0.28

105.0 0.27

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4.2.2 MS-MS

1 of 8
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

303.2319 100

285.2212 6.14

267.2104 1.80

175.1493 1.04

Thumbnail
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2 of 8
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

303.2321 100

175.1491 10.04

285.2217 9.68

221.1544 8.32

93.069 6.60

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4.2.3 LC-MS

1 of 18
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6560 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
40 eV
Fragmentation Mode
CID
Retention Time
0.187 min
Precursor m/z
301.2173
Precursor Adduct
[M-H]-
Top 5 Peaks

217.0647 999

91.0201 775

99.0797 430

149.0067 337

199.022 315

Thumbnail
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License
CC BY
2 of 18
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6560 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Retention Time
0.187 min
Precursor m/z
301.2173
Precursor Adduct
[M-H]-
Top 5 Peaks

301.2166 999

257.2262 288

203.1774 141

273.1818 54

187.145 41

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License
CC BY

4.2.4 Other MS

1 of 2
MS Category
In-Silico
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
301.21676
Instrument
SCIEX 5600
Instrument Type
in-silico QTOF
Ionization Mode
negative
Collision Energy
45 V
Retention Time
3.46
Top 5 Peaks
301.2168 100
Thumbnail
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2 of 2
MS Category
In-Silico
MS Type
Other
Precursor Type
[M-H]-
Precursor m/z
301.2173
Ionization Mode
negative
Retention Time
5.52
Top 5 Peaks
301.2173 100
Thumbnail
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4.3 IR Spectra

4.3.1 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
277851
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

EPA can be used for lowering elevated triglycerides in those who are hyperglyceridemic. In addition, EPA may play a therapeutic role in patients with cystic fibrosis by reducing disease severity and may play a similar role in type 2 diabetics in slowing the progression of diabetic nephropathy.
Treatment of Familial Adenomatous Polyposis

7.2 FDA National Drug Code Directory

7.3 Drug Labels

Drug and label
Active ingredient and drug

7.4 Clinical Trials

7.4.1 ClinicalTrials.gov

7.4.2 EU Clinical Trials Register

7.4.3 NIPH Clinical Trials Search of Japan

7.5 EMA Drug Information

Type
Paediatric investigation
Active Substance
Therapeutic Area
Gastroentology-Hepatology
Drug Form
Gastro-resistant capsule, Capsule, soft
Administration Route
Oral use
Decision Type
W: decision granting a waiver in all age groups for all conditions or indications
Decision Date
2011-11-28

7.6 Biomarker Information

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Pharmacodynamics

Eicosanoids are chemical messengers derived from 20-carbon polyunsaturated fatty acids that play critical roles in immune and inflammatory responses. Both 20-carbon omega-6 fatty acids (arachidonic acid) and 20-carbon omega-3 fatty acids (EPA) can be found in cell membranes. During an inflammatory response, arachidonic acid and EPA are metabolized by enzymes known as cyclooxygenases and lipoxygenases to form eicosanoids. Increasing omega-3 fatty acid intake increases the EPA content of cell membranes and decreases the arachidonic acid content, resulting in higher proportions of eicosanoids derived from EPA. Physiologic responses to arachidonic acid-derived eicosanoids differ from responses to EPA-derived eicosanoids. In general, eicosanoids derived from EPA are less potent inducers of inflammation, blood vessel constriction, and clotting than eicosanoids derived from arachidonic acid.

9.2 Metabolism / Metabolites

Eicosapentaenoic acid has known human metabolites that include Juniperonic acid.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

9.3 Mechanism of Action

The anti-inflammatory, antithrombotic and immunomodulatory actions of EPA is probably due to its role in eicosanoid physiology and biochemistry. Most eicosanoids are produced by the metabolism of omega-3 fatty acids, specifically, arachidonic acid. These eicosanoids, leukotriene B4 (LTB4) and thromboxane A2 (TXA2) stimulate leukocyte chemotaxis, platelet aggregation and vasoconstriction. They are thrombogenic and artherogenic. On the other hand, EPA is metabolized to leukotriene B5 (LTB5) and thromboxane A3 (TXA3), which are eicosanoids that promote vasodilation, inhibit platelet aggregation and leukocyte chemotaxis and are anti-artherogenic and anti-thrombotic. The triglyceride-lowering effect of EPA results from inhibition of lipogenesis and stimulation of fatty acid oxidation. Fatty acid oxidation of EPA occurs mainly in the mitochondria. EPA is a substrate for Prostaglandin-endoperoxide synthase 1 and 2. It also appears to affect the function and bind to the Carbohydrate responsive element binding protein (ChREBP) and to a fatty acid receptor (G-coupled receptor) known as GP40.

9.4 Human Metabolite Information

9.4.1 Tissue Locations

  • Adipose Tissue
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Kidney
  • Leukocyte
  • Liver
  • Placenta
  • Platelet
  • Skeletal Muscle

9.4.2 Cellular Locations

  • Extracellular
  • Membrane

9.4.3 Metabolite Pathways

9.5 Biochemical Reactions

9.6 Transformations

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

Use (kg; approx.) in Germany (2009): >5000

Consumption (g per capita; approx.) in Germany (2009): 0.0611

Calculated removal (%): 99.9

10.1.1 Use Classification

Human Drugs -> EU pediatric investigation plans
Cosmetics -> Emollient; Skin conditioning
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Pictogram(s)
Corrosive
Signal
Danger
GHS Hazard Statements
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
Precautionary Statement Codes

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, 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 92 reports by companies from 1 notifications to the ECHA C&L Inventory.

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 Corr. 1B (100%)

11.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-: 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

Disease
Colorectal cancer
References

PubMed: 7482520, 22148915, 19006102, 23940645, 24424155, 20156336, 19678709, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Major depressive disorder
References
Disease
Essential hypertension
References
Disease
Isovaleric acidemia
References

PubMed: 15615815, 12837870, 11978597, 17850781, 19343532, 27329611, 1246461

Isovaleric acidemia: Therapeutic response to supplementation with glycine, /react-text l react-text: 82 -carnitine, or both in combination and a 10-year. follow-up case study. Molecular Genetics and Metabolism Reports. Volume 11, June 2017, Pages 2-5

MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Nature Journal References

13.6 Chemical Co-Occurrences in Literature

13.7 Chemical-Gene Co-Occurrences in Literature

13.8 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 Drug-Drug Interactions

15.4 Pathways

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us

18 Classification

18.1 MeSH Tree

18.2 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 LIPID MAPS Classification

18.5 KEGG: Metabolite

18.6 KEGG: Lipid

18.7 KEGG: Phytochemical Compounds

18.8 ChemIDplus

18.9 ChEMBL Target Tree

18.10 UN GHS Classification

18.11 EPA CPDat Classification

18.12 NORMAN Suspect List Exchange Classification

18.13 CCSBase Classification

18.14 EPA DSSTox Classification

18.15 Consumer Product Information Database Classification

18.16 LOTUS Tree

18.17 CCS Classification - Baker Lab

18.18 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Baker Lab, Chemistry Department, The University of North Carolina at Chapel Hill
    FA 20:5
    CCS Classification - Baker Lab
    https://tarheels.live/bakerlab/
  2. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  3. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  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. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  7. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  8. 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
  9. 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
  10. 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
  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. ChEBI
    All-cis-5,8,11,14,17-icosapentaenoic acid
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28364
  13. 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/
  14. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  15. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  16. 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
  17. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  18. 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
  19. 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
  20. Therapeutic Target Database (TTD)
  21. DailyMed
  22. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  23. ECI Group, LCSB, University of Luxembourg
    LICENSE
    Data: CC-BY 4.0; Code: Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Timnodonic acid
  24. KNApSAcK Species-Metabolite Database
  25. Natural Product Activity and Species Source (NPASS)
  26. West Coast Metabolomics Center-UC Davis
    FA 20:5; (eicosapentaenoic acid)
  27. EPA Chemical and Products Database (CPDat)
  28. 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/
    EICOSAPENTAENOIC ACID
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  29. EU Clinical Trials Register
  30. 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
    (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate
    https://foodb.ca/compounds/FDB030126
  31. 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
  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
    5,8,11,14,17-Eicosapentaenoic acid
    http://www.nist.gov/srd/nist1a.cfm
  33. SpectraBase
    5,8,11,14,17-EICOSAPENTAENOIC-ACID;C20:5OMEGA3;EPA;FJ-2
    https://spectrabase.com/spectrum/5FNu7UswwB9
    cis-5,8,11,14,17-Eicosapentaenoic acid
    https://spectrabase.com/spectrum/90ewcjiPV1S
    cis-5,8,11,14,17-Eicosapentaenoic acid
    https://spectrabase.com/spectrum/xoBkDyzJcF
    cis-5,8,11,14,17-Eicosapentaenoic acid
    https://spectrabase.com/spectrum/12SexKJM9aM
  34. Japan Chemical Substance Dictionary (Nikkaji)
  35. 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
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    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  37. MassBank Europe
  38. National Drug Code (NDC) Directory
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  39. Nature Chemistry
  40. NIPH Clinical Trials Search of Japan
  41. NLM RxNorm Terminology
    LICENSE
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  42. PharmGKB
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    https://www.pharmgkb.org/page/policies
  43. Protein Data Bank in Europe (PDBe)
  44. 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
  45. Springer Nature
  46. SpringerMaterials
  47. 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/
  48. Wikidata
  49. Wikipedia
  50. Medical Subject Headings (MeSH)
    LICENSE
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    https://www.nlm.nih.gov/copyright.html
  51. PubChem
  52. GHS Classification (UNECE)
  53. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  54. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  55. PATENTSCOPE (WIPO)
  56. NCBI
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