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DL-Alanine

PubChem CID
602
Structure
DL-Alanine_small.png
DL-Alanine_3D_Structure.png
Molecular Formula
Synonyms
  • DL-ALANINE
  • 302-72-7
  • alanine
  • 2-Aminopropanoic acid
  • DL-2-Aminopropionic acid
Molecular Weight
89.09 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-04
Description
Alanine is an alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2. It has a role as a fundamental metabolite. It is functionally related to a propionic acid. It is a conjugate base of an alaninium. It is a conjugate acid of an alaninate. It is a tautomer of an alanine zwitterion.
Alanine is a non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and the central nervous system.
DL-Alanine has been reported in Drosophila melanogaster, Populus tremula, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
DL-Alanine.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-DL-Ala-OH
Sequence
A
PLN
H-A-OH
HELM
PEPTIDE1{(A,[dA])}$$$$V2.0
IUPAC
DL-alanine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

2-aminopropanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

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

3.1.4 SMILES

CC(C(=O)O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C3H7NO2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

302-72-7
56-41-7
338-69-2

3.3.3 European Community (EC) Number

3.3.4 UNII

3.3.5 ChEBI ID

3.3.6 ChEMBL ID

3.3.7 DrugBank ID

3.3.8 DSSTox Substance ID

3.3.9 FEMA Number

3.3.10 HMDB ID

3.3.11 JECFA Number

1437

3.3.12 KEGG ID

3.3.13 Metabolomics Workbench ID

3.3.14 NCI Thesaurus Code

3.3.15 Nikkaji Number

3.3.16 NSC Number

3.3.17 RXCUI

3.3.18 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • Abufène
  • Alanine
  • Alanine, L Isomer
  • Alanine, L-Isomer
  • L Alanine
  • L-Alanine
  • L-Isomer Alanine

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
89.09 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-3
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
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
89.047678466 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
89.047678466 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
63.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
6
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
61.8
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
1
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)

4.2 Experimental Properties

4.2.1 Physical Description

Solid; [Merck Index] White odorless solid; [HSDB] White crystalline solid; [Sigma-Aldrich MSDS]
Solid; [Merck Index] White powder; [Sigma-Aldrich MSDS]
White crystalline powder; odourless

4.2.2 Melting Point

300 dec °C
PhysProp

4.2.3 Solubility

164000 mg/L (at 25 °C)
YALKOWSKY,SH & DANNENFELSER,RM (1992)
Solublein water
Slightly soluble (in ethanol)

4.2.4 Vapor Pressure

0.00000011 [mmHg]

4.2.5 LogP

-2.85
SANGSTER (1994)

4.2.6 Dissociation Constants

pKa
2.34 (at 25 °C)
KORTUM,G ET AL (1961)

4.3 Chemical Classes

Biological Agents -> Amino Acids and Derivatives

4.3.1 Cosmetics

Cosmetic ingredients (Alanine) -> CIR (Cosmetic Ingredient Review)
Antistatic
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

4.3.2 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 1H NMR Spectra

1 of 4
View All
Spectra ID
Frequency
600 MHz
Solvent
H2O
Shifts [ppm]
2.30
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2 of 4
View All
Spectra ID
Instrument Type
JEOL
Frequency
400 MHz
Solvent
D2O
Shifts [ppm]:Intensity
1.47:962.00, 3.81:92.00, 3.78:297.00, 3.80:293.00, 1.49:1000.00, 3.76:99.00
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5.1.2 13C NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
JEOL
Frequency
22.5 MHz
Solvent
D2O
pH
6.38
Shifts [ppm]:Intensity
176.60:218.00, 51.66:740.00, 17.26:1000.00
Thumbnail
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2 of 3
View All
Source of Sample
MCB Manufacturing Chemists, Norwood, Ohio
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.1.3 17O NMR Spectra

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

5.2.1 GC-MS

1 of 11
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

44.0 99.99

18.0 25.52

28.0 14.89

42.0 12.09

15.0 5.83

Thumbnail
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Notes
instrument=HITACHI M-80A
2 of 11
View All
Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

116.0 100

147.0 19.12

117.0 12.41

100.0 7.01

103.0 4.60

Thumbnail
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Notes
instrument=Leco Pegasus IV

5.2.2 MS-MS

1 of 9
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

90.056 100

44.049 60.96

Thumbnail
Thumbnail
2 of 9
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

44.0486 100

44.9959 15.03

42.0333 9.51

43.0397 2.64

55.0149 1.78

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5.2.3 LC-MS

1 of 9
View All
Authors
Boettcher C, Institute of Plant Biochemistry, Halle, Germany
Instrument
API QSTAR Pulsar i
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Precursor Adduct
[M+H]+
Top 5 Peaks

90.056 999

44.049 609

Thumbnail
Thumbnail
License
CC BY-SA
2 of 9
View All
Authors
Sawada Y, Matsuda F, and Hirai MY. Plant Science Center, RIKEN
Instrument
TQD, Waters
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10
Precursor m/z
90.06
Top 5 Peaks

44 999

90 723

43 289

89 164

Thumbnail
Thumbnail
License
CC BY-NC
Reference
Sawada, Y.; Akiyama, K.; Sakata, A.; Kuwahara, A.; Otsuki, H.; Sakurai, T.; Saito, K.; Hirai, M. Y. Widely Targeted Metabolomics Based on Large-Scale MS/MS Data for Elucidating Metabolite Accumulation Patterns in Plants. Plant and Cell Physiology 2008, 50 (1), 37-47. DOI:10.1093/pcp/pcn183

5.2.4 Other MS

Authors
TAJIMA S, GUNMA COLLEGE OF TECHNOLOGY
Instrument
HITACHI M-80A
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

44 999

18 255

28 149

42 121

15 58

Thumbnail
Thumbnail
License
CC BY-NC-SA

5.3 IR Spectra

5.3.1 FTIR Spectra

1 of 2
Technique
SPLIT MULL
Source of Sample
The Matheson Company, Inc., East Rutherford, New Jersey
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker IFS 85
Technique
KBr-Pellet
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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5.3.2 ATR-IR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Spectrochem Pvt. Ltd.
Catalog Number
101137
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
135224
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.4 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Spectrochem Pvt. Ltd., India
Catalog Number
101137
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Catalog Number
135224
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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7 Chemical Vendors

8 Drug and Medication Information

8.1 Drug Indication

Used for protein synthesis.

8.2 FDA National Drug Code Directory

8.3 Drug Labels

Active ingredient and drug

8.4 Clinical Trials

8.4.1 ClinicalTrials.gov

8.4.2 EU Clinical Trials Register

8.4.3 NIPH Clinical Trials Search of Japan

9 Food Additives and Ingredients

9.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

9.2 FDA Substances Added to Food

Substance
Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
Document Number (21 eCFR)
FEMA Number
3818
GRAS Number
18, 25
JECFA Flavor Number
1437

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

Chemical Name
DL-ALANINE
Evaluation Year
2004
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

10 Pharmacology and Biochemistry

10.1 Pharmacodynamics

Is an important source of energy for muscle tissue, the brain and central nervous system; strengthens the immune system by producing antibodies; helps in the metabolism of sugars and organic acids.

10.2 Mechanism of Action

L-Alanine is a non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and the central nervous system. BCAAs are used as a source of energy for muscle cells. During prolonged exercise, BCAAs are released from skeletal muscles and their carbon backbones are used as fuel, while their nitrogen portion is used to form another amino acid, Alanine. Alanine is then converted to Glucose by the liver. This form of energy production is called the Alanine-Glucose cycle, and it plays a major role in maintaining the body's blood sugar balance.

10.3 Biochemical Reactions

11 Use and Manufacturing

11.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Alanine
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
Sources/Uses
A non-essential amino acid; [Merck Index] Used in microbiological and biochemical research and as a dietary supplement; [HSDB] Used as a flavoring agent; [FDA]
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.
Sources/Uses
A non-essential amino acid; [Merck Index] Used as a flavoring agent or adjuvant; [FDA]
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.

Use (kg; approx.) in Germany (2009): >25000

Consumption (g per capita; approx.) in Germany (2009): 0.305

Calculated removal (%): 92.1

11.1.1 Use Classification

Food additives -> Flavoring Agents
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Cosmetics -> Antistatic
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

11.1.2 Household Products

Household & Commercial/Institutional Products

Information on 33 consumer products that contain Alanine in the following categories is provided:

• Personal Care

11.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Alanine: ACTIVE

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 98.9% (258 of 261) of all reports. Pictograms displayed are for 1.1% (3 of 261) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 258 of 261 companies (only 1.1% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 261 reports by companies from 4 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 258 of 261 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 3 notifications provided by 3 of 261 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.

12.1.2 Hazard Classes and Categories

Not Classified

12.1.3 Hazards Summary

May cause irritation; [Sigma-Aldrich MSDS]
Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Sigma-Aldrich MSDS]

12.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: DL-Alanine
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Alanine: Does not have an individual approval but may be used under an appropriate group standard

12.3 Other Safety Information

Chemical Assessment

IMAP assessments - DL-Alanine: Environment tier I assessment

Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health

13 Associated Disorders and Diseases

Disease
Pregnancy
References

PubMed: 2994907, 663967, 12698507, 17061063, 3252730, 12833386, 17704099, 16925883, 22420377, 18059417, 22494326, 23159745, 23313728, 23535240, 24704061

The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Wiley References

14.6 Chemical Co-Occurrences in Literature

14.7 Chemical-Gene Co-Occurrences in Literature

14.8 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Protein Bound 3D Structures

16.2 Chemical-Target Interactions

16.3 Pathways

17 Biological Test Results

17.1 BioAssay Results

18 Taxonomy

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

19 Classification

19.1 MeSH Tree

19.2 NCI Thesaurus Tree

19.3 ChEBI Ontology

19.4 KEGG: Risk Category of Japanese OTC Drugs

19.5 ChemIDplus

19.6 UN GHS Classification

19.7 EPA CPDat Classification

19.8 NORMAN Suspect List Exchange Classification

19.9 EPA DSSTox Classification

19.10 Consumer Product Information Database Classification

19.11 EPA TSCA and CDR Classification

19.12 LOTUS Tree

19.13 EPA Substance Registry Services Tree

19.14 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
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    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DrugBank
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  6. EPA Chemicals under the 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)
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    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
    (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein)
    http://www.hmdb.ca/metabolites/HMDB0062251
  11. New Zealand Environmental Protection Authority (EPA)
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    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. Consumer Product Information Database (CPID)
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    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/
  19. Cosmetic Ingredient Review (CIR)
  20. EPA Chemical and Products Database (CPDat)
  21. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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  22. NORMAN Suspect List Exchange
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    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    ALANINE
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  23. DailyMed
  24. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
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    https://www.who.int/about/policies/publishing/copyright
  25. IUPAC Digitized pKa Dataset
  26. EU Clinical Trials Register
  27. EU Food Improvement Agents
  28. FDA Substances Added to Food
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  29. Flavor and Extract Manufacturers Association (FEMA)
  30. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  31. NIST Mass Spectrometry Data Center
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    https://www.nist.gov/srd/public-law
  32. SpectraBase
  33. Japan Chemical Substance Dictionary (Nikkaji)
  34. 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
    Risk category of Japanese OTC drugs
    http://www.genome.jp/kegg-bin/get_htext?br08312.keg
  35. Natural Product Activity and Species Source (NPASS)
  36. MassBank Europe
  37. Metabolomics Workbench
  38. 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
  39. NIPH Clinical Trials Search of Japan
  40. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  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. Wiley
  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. EPA Substance Registry Services
  49. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  50. PATENTSCOPE (WIPO)
CONTENTS