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Lutein

PubChem CID
5281243
Structure
Lutein_small.png
Lutein_3D_Structure.png
Molecular Formula
Synonyms
  • Lutein
  • XANTHOPHYLL
  • 127-40-2
  • Bo-Xan
  • Vegetable lutein
Molecular Weight
568.9 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-04
Description
Lutein is a carotenol. It has a role as a food colouring and a plant metabolite. It derives from a hydride of a (6'R)-beta,epsilon-carotene.
Lutein is an xanthophyll and one of 600 known naturally occurring carotenoids. Lutein is synthesized only by plants and like other xanthophylls is found in high quantities in green leafy vegetables such as spinach, kale and yellow carrots. In green plants, xanthophylls act to modulate light energy and serve as non-photochemical quenching agents to deal with triplet chlorophyll (an excited form of chlorophyll), which is overproduced at very high light levels, during photosynthesis.
Lutein has been reported in Erythrophleum fordii, Nephrolepis cordifolia, and other organisms with data available.
See also: Calendula Officinalis Flower (part of); Corn (part of); Chicken; lutein (component of).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Lutein.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

KBPHJBAIARWVSC-RGZFRNHPSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H]2C(=C[C@@H](CC2(C)C)O)C)/C)/C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C40H56O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

127-40-2

2.3.2 Deprecated CAS

1407-74-5, 148124-35-0, 25312-96-3, 28368-07-2, 34026-62-5, 34445-91-5

2.3.3 European Community (EC) Number

204-840-0

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 Metabolomics Workbench ID

2.3.13 NCI Thesaurus Code

2.3.14 Nikkaji Number

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • beta,epsilon-Carotene-3, 3'-Diol, (3R,3'R,6'S)-
  • beta,epsilon-Carotene-3,3'-diol, (3S,3'R,6'S)-
  • gamma Lutein
  • Lutein
  • Lutein F
  • Lutein G
  • Lutein, gamma

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
568.9 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
11
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
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
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
568.42803102 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
568.42803102 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
40.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
42
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1270
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
3
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
9
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

Dark, yellowish brown liquid
Solid

3.2.2 Melting Point

196 °C
PhysProp
196 °C

3.2.3 Solubility

Insoluble

3.2.4 LogP

7.9

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

3.3.2 Food Additives

Foods -> FDA Regulatory Status of Color Additives
Use unspecified -> FDA Substance added to food

3.3.3 Lipids

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C40 isoprenoids (tetraterpenes) [PR0107]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 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 © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 4
View All
NIST Number
26538
Library
Main library
Total Peaks
518
m/z Top Peak
91
m/z 2nd Highest
105
m/z 3rd Highest
119
Thumbnail
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2 of 4
View All
NIST Number
100414
Library
Replicate library
Total Peaks
211
m/z Top Peak
41
m/z 2nd Highest
56
m/z 3rd Highest
54
Thumbnail
Thumbnail

4.2.2 MS-MS

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

338.26 100

568.427 92.04

476.364 61.63

569.43 57.28

145.101 40.73

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

568.427 100

338.26 95.83

476.365 91.33

569.43 58.71

145.101 48.34

Thumbnail
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4.2.3 LC-MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
567
Instrument
Esquire
Instrument Type
QIT
Ionization
ESI
Ionization Mode
negative
Collision Energy
43.2->8V
Top 5 Peaks
567 100
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Thumbnail
2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
569
Instrument
Esquire 4000
Instrument Type
QIT
Ionization
ESI
Ionization Mode
positive
Collision Energy
20->10V
Top 5 Peaks

463 100

533 100

551 100

Thumbnail
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4.2.4 Other MS

1 of 2
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M]+*
Precursor m/z
568.43
Instrument
JMS-HX/HX 110A, JEOL
Instrument Type
FAB-EBEB
Ionization
FAB
Ionization Mode
positive
Collision Energy
3 kV
Top 5 Peaks

568.4209 99.96

105.0856 66.10

119.0823 62.01

145.0845 54.54

91.0674 54.23

Thumbnail
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License
CC BY-SA
2 of 2
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS1
Instrument
JMS-HX/HX 110A, JEOL
Instrument Type
EI-EBEB
Ionization
EI
Ionization Mode
positive
Top 5 Peaks

550.0000 91.63

568.0000 55.48

551.0000 40.46

569.0000 24.43

552.0000 11.34

Thumbnail
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License
CC BY-SA

4.3 UV Spectra

Maximum in chloroform/ethanol (1:9) at ca. 445 nm

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Xanthophylls are taken for nutritional supplementation, and also for treating dietary shortage or imbalance.

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 Biomarker Information

8 Food Additives and Ingredients

8.1 Food Additive Classes

JECFA Functional Classes
Food Additives -> COLOUR; NUTRIENT_SUPPLEMENT;
JECFA Functional Classes
Food Additives -> COLOUR;
JECFA Functional Classes
COLOUR;

8.2 Food Additive Definition

EU Food Additive Definition
Lutein is obtained by solvent extraction of the strains of edible fruits and plants, grass, lucerne (alfalfa) andTagetes erecta. The main colouring principle consists of carotenoids of which lutein and its fatty acid esters account for the major part. Variable amounts of carotenes will also be present. Lutein may contain fats, oils and waxes naturally occurring in the plant material.; Only the following solvents may be used for the extraction: methanol, ethanol, propan-2-ol, hexane, acetone, methyl ethyl ketone and carbon dioxide

8.3 FDA Substances Added to Food

Substance
Used for (Technical Effect)
Use unspecified
Document Number (21 eCFR)

8.4 Color Additive Status

Color Additive
Use
Foods
End Note
1 - The color additives Antarctic krill meal, Astaxanthin, Astaxanthin dimethyldisuccinate, Ultramarine blue, Canthaxanthin, Haematococcus algae meal, Synthetic iron oxide, Dried algae meal, Tagetes (Aztec marigold) meal and extract, Corn endosperm oil, Paracoccus pigment, and Phaffia yeast are approved for specific uses in animal food (see 21 CFR 73.32. 73.35, 73.37, 73.50, 73.75, 73.185, 73.200, 73.275, 73.295, 73.315, 73.352, and 73.355, respectively).
Color additive regulations in 21 eCFR

8.5 Associated Foods

8.6 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

1 of 3
Chemical Name
BO-XAN
Evaluation Year
2018
ADI
NOT SPECIFIED (group ADI for lutein from Tagetes erecta, lutein esters from Tagetes erecta and zeaxanthin (synthetic))
Comments
Based on the absence of toxicity in a wide range of studies, the Committee at it's 86th meeting established a group ADI "not specified" for lutein from Tagetes erecta, lutein esters from Tagetes erecta and zeaxanthin (synthetic).
Tox Monograph
2 of 3
Chemical Name
XANTHOPHYLLS
Evaluation Year
1977
ADI
NO ADI ALLOCATED
Comments
JECFA noted that no toxicity data were available, thus no evaluation could be made nor could an ADI be established.
Tox Monograph
3 of 3
Chemical Name
LUTEIN from TAGETES ERECTA
Evaluation Year
2018
ADI
NOT SPECIFIED (group ADI for lutein from Tagetes erecta, lutein esters from Tagetes erecta and zeaxanthin (synthetic))
Comments
Based on the absence of toxicity in a wide range of studies, the Committee at it's 86th meeting established a group ADI "not specified" for lutein from Tagetes erecta, lutein esters from Tagetes erecta and zeaxanthin (synthetic).
Tox Monograph

9 Pharmacology and Biochemistry

9.1 Pharmacodynamics

Lutein was found to be present in a concentrated area of the macula, a small area of the retina responsible for central vision. The hypothesis for the natural concentration is that lutein helps protect from oxidative stress and high-energy light. Several studies show that an increase in macula pigmentation decreases the risk for eye diseases such as Age-related Macular Degeneration (AMD).

9.2 Mechanism of Action

Xanthophylls have antioxidant activity and react with active oxygen species, producing biologically active degradation products. They also can inhibit peroxidation of membrane phospholipids and reduce lipofuscin formation, both of which contribute to their antioxidant properties. Lutein is naturally present in the macula of the human retina. It filters out potentially phototoxic blue light and near-ultraviolet radiation from the macula. The protective effect is due in part, to the reactive oxygen species quenching ability of these carotenoids. Lutein is more stable to decomposition by pro-oxidants than are other carotenoids such as beta-carotene and lycopene. Lutein is abundant in the region surrounding the fovea, and lutein is the predominant pigment at the outermost periphery of the macula. Zeaxanthin, which is fully conjugated (lutein is not), may offer somewhat better protection than lutein against phototoxic damage caused by blue and near-ultraviolet light radiation. Lutein is one of only two carotenoids that have been identified in the human lens, may be protective against age-related increases in lens density and cataract formation. Again, the possible protection afforded by lutein may be accounted for, in part, by its reactive oxygen species scavenging abilities. Carotenoids also provide protection from cancer. One of the mechanisms of this is by increasing the expression of the protein connexin-43, thereby stimulating gap junctional communication and preventing unrestrained cell proliferation.

9.3 Human Metabolite Information

9.3.1 Tissue Locations

  • Adipose Tissue
  • Adrenal Gland
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Neuron
  • Ovary
  • Placenta
  • Retina
  • Spleen
  • Testis

9.3.2 Cellular Locations

  • Extracellular
  • Membrane

9.4 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

10.1.1 Use Classification

Food additives
Food Additives -> COLOUR; NUTRIENT_SUPPLEMENT; -> JECFA Functional Classes
Food Additives -> COLOUR; -> JECFA Functional Classes
COLOUR; -> JECFA Functional Classes

10.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
.beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-: ACTIVE

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 95% (134 of 141) of all reports. Pictograms displayed are for 5% (7 of 141) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 134 of 141 companies (only 5% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 141 reports by companies from 4 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 134 of 141 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 2 notifications provided by 7 of 141 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.

11.1.2 Hazard Classes and Categories

Not Classified

11.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: .beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-
New Zealand EPA Inventory of Chemical Status
.beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-: 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
Diabetes mellitus type 1
References

PubMed: 12067838, 22279428, 16452910

Lorena Ivona ŞTEFAN, Alina NICOLESCU, Simona POPA, Maria MOŢA, Eugenia KOVACS and Calin DELEANU. 1H-NMR URINE METABOLIC PROFILING IN TYPE 1 DIABETES MELLITUS. Rev. Roum. Chim., 2010, 55(11-12), 1033-1037

Disease
Obesity
References

PubMed: 15899597, 17264178, 16253646, 2401584, 1783639, 26505825, 17408529, 18997681, 24740590, 23108202, 26910390

Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

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

15.2 Chemical-Target Interactions

15.3 Drug-Food Interactions

Take with foods containing vitamin C. Taking lutein with vitamin C may increase the rate of absorption of lutein. Taking lutein with carotenoids or naringenin may reduce lutein absorption.

15.4 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 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 LIPID MAPS Classification

18.5 KEGG: Lipid

18.6 KEGG: Phytochemical Compounds

18.7 ChemIDplus

18.8 ChEMBL Target Tree

18.9 UN GHS Classification

18.10 EPA CPDat Classification

18.11 NORMAN Suspect List Exchange Classification

18.12 EPA DSSTox Classification

18.13 EPA TSCA and CDR Classification

18.14 LOTUS Tree

18.15 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    .beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-
    https://services.industrialchemicals.gov.au/search-inventory/
  2. EU Food Improvement Agents
  3. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. DrugBank
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    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
  6. EPA Chemicals under the TSCA
    .beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  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)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  10. Human Metabolome Database (HMDB)
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    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
  13. LOTUS - the natural products occurrence database
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    https://lotus.nprod.net/
  14. NCI Thesaurus (NCIt)
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  15. Open Targets
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  16. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  17. ClinicalTrials.gov
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    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. DailyMed
  20. EPA Chemical and Products Database (CPDat)
  21. EU Clinical Trials Register
  22. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence.
    https://www.who.int/about/policies/publishing/copyright
  23. FDA Regulatory Status of Color Additives
  24. FDA Substances Added to Food
    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
  25. FooDB
    LICENSE
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    https://foodb.ca/about
  26. 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
  27. Japan Chemical Substance Dictionary (Nikkaji)
  28. 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
  29. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  30. Natural Product Activity and Species Source (NPASS)
  31. MarkerDB
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    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  32. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  33. Metabolomics Workbench
  34. National Drug Code (NDC) Directory
    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
  35. Nature Chemical Biology
  36. NIPH Clinical Trials Search of Japan
  37. SpectraBase
    (all-E,3R,3'R,6'R)-beta,xi-Carotene-3,3'-diol
    https://spectrabase.com/spectrum/5SI4xlx1kgb
    LUTEIN;(3R,3'R,6'R)-BETA,EPSILON-CAROTENE-3,3'-DIOL
    https://spectrabase.com/spectrum/HeYwsds5BJK
  38. 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/
    Lutein
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  39. 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
  40. 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
  41. Springer Nature
  42. 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/
  43. Wikidata
  44. Wikipedia
  45. 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
  46. PubChem
  47. GHS Classification (UNECE)
  48. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  49. PATENTSCOPE (WIPO)
CONTENTS