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Heptadecanoic acid

PubChem CID
10465
Structure
Heptadecanoic acid_small.png
Heptadecanoic acid_3D_Structure.png
Heptadecanoic acid__Crystal_Structure.png
Molecular Formula
Synonyms
  • HEPTADECANOIC ACID
  • 506-12-7
  • Margaric acid
  • n-Heptadecanoic acid
  • Margarinic acid
Molecular Weight
270.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-02-01
Description
Heptadecanoic acid is a C17 saturated fatty acid and trace component of fats in ruminants. It has a role as a mammalian metabolite, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a margarate.
Margaric acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Heptadecanoic acid has been reported in Hoya crassipes, Hoya pseudolanceolata, and other organisms with data available.
See also: Fatty acids, C14-22 (annotation moved to); Fatty acids, C16-18 (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Heptadecanoic acid.png

1.2 3D Conformer

1.3 Crystal Structures

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

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

heptadecanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CCCCCCCCCCCCCCCCC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C17H34O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

506-12-7
63399-94-0
67701-03-5
68424-37-3

2.3.3 Deprecated CAS

28829-31-4, 45237-51-2, 45237-52-3
1000206-53-0, 1051372-93-0, 1338-46-1, 1588986-68-8, 176435-16-8, 2102098-08-6, 2135640-81-0, 2368179-17-1, 39390-60-8, 52051-63-5, 67255-22-5, 736166-71-5, 7722-21-6, 8000-11-1, 8034-56-8, 8034-57-9, 8034-58-0, 8037-82-9, 8043-36-5
37231-04-2

2.3.4 European Community (EC) Number

2.3.5 UNII

2.3.6 ChEBI ID

2.3.7 ChEMBL ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 Lipid Maps ID (LM_ID)

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 NSC Number

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • heptadecanoic acid
  • margaric acid
  • margaric acid, 1-(11)C-labeled
  • margaric acid, nickel (2+) salt
  • margaric acid, potassium salt
  • margaric acid, sodium salt
  • omega I-123 heptadecanoic acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
270.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
6.9
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
15
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
270.255880323 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
270.255880323 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
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
190
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

Liquid, Other Solid
Solid; [Merck Index]
Solid

3.2.2 Boiling Point

363.00 to 364.00 °C. @ 760.00 mm Hg
The Good Scents Company Information System

3.2.3 Melting Point

61.3 °C

3.2.4 Solubility

4.2 mg/L @ 25 °C (exp)
The Good Scents Company Information System

3.2.5 Collision Cross Section

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

173.1 Ų [M-H]-

171.9 Ų [M+Cl]-

189.6 Ų [M+H]+

172.8 Ų [M-H]-

164.1 Ų [M-H]-

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

3.2.6 Kovats Retention Index

Standard non-polar
2038 , 2039 , 2038 , 2039 , 2047 , 2044 , 2059 , 351.5 , 351.7
Semi-standard non-polar
2080 , 2086 , 2069 , 2022 , 2077 , 2068 , 2077 , 2070 , 2071 , 2080 , 2065 , 337
Standard polar
3027 , 2975 , 2968 , 3035.9 , 2974 , 2988.4 , 2979 , 2981

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Biological Agents -> Fatty Acids and Fats

3.4.1 Lipids

Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 4
View All
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
CDCl3
pH
Not Applic
Shifts [ppm]:Intensity
1.29:6.28, 2.34:8.13, 1.63:4.93, 1.28:7.94, 1.25:100.00, 2.35:12.81, 1.30:5.18, 1.62:3.80, 0.89:8.37, 0.87:10.07, 1.34:1.62, 0.88:21.21, 1.64:3.26, 1.35:1.63, 1.33:2.35, 2.36:7.51, 1.32:2.83, 1.31:3.39, 1.61:1.60, 1.66:1.16, 1.34:2.71
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Spectra ID
Instrument Type
JEOL
Frequency
90 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
2.35:30.00, 1.26:1000.00, 2.26:23.00, 0.88:59.00
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4.1.2 13C NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
Varian
Frequency
25.16 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
14.12:166.00, 29.40:286.00, 29.28:230.00, 29.10:207.00, 29.46:295.00, 29.72:1000.00, 22.72:166.00, 34.14:161.00, 24.71:166.00, 180.49:253.00, 31.97:175.00
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Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
CDCl3
pH
Not Applic
Shifts [ppm] (F2:F1):Intensity
1.34:29.18:0.05, 1.63:24.67:0.07, 1.25:31.87:0.07, 2.35:33.85:0.11, 0.88:14.28:0.01, 1.29:22.68:0.03, 1.26:29.55:1.00
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 13
View All
Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

117.0 100

132.0 47.75

129.0 46.45

145.0 23.42

131.0 16.02

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Notes
instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies
2 of 13
View All
Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

117.0 1

129.0 0.44

132.0 0.39

145.0 0.22

327.0 0.15

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4.3.2 MS-MS

1 of 7
View All
Spectra ID
Instrument Type
LC-ESI-QTOF
Ionization Mode
positive
Top 5 Peaks

240.2293 26.38

240.2249 8.43

240.2271 6.82

240.2227 6.59

271.272 5.30

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Notes
adduct_type [M+H]+ original_collision_energy 35 eV CannabisDB spectra from MoNa 2020 June SCIEX TripleTOF 6600 Fiehn HILIC Library
2 of 7
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

240.22925 100

271.27197 20.10

95.0733 5.02

254.23558 5.02

109.09554 5.02

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4.3.3 LC-MS

1 of 15
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
0.146 min
Precursor m/z
269.2486
Precursor Adduct
[M-H]-
Top 5 Peaks

81.0344 999

121.1205 203

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License
CC BY
2 of 15
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
0.147 min
Precursor m/z
269.2486
Precursor Adduct
[M-H]-
Top 5 Peaks

269.2489 999

107.1446 1

110.2244 1

108.1543 1

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License
CC BY

4.3.4 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Instrument Type
ESI-TOF
Ionization Mode
negative
Top 5 Peaks

269.2495 100

270.2525 15.62

369.1742 5.31

430.0095 2.90

271.2553 1.70

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2 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Instrument Type
ESI-TOF
Ionization Mode
negative
Top 5 Peaks

269.2495 100

270.2525 15.62

369.1742 5.31

430.0095 2.90

279.0094 1.70

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4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
Recrystallized layer between CsI
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.4.2 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
Acros Organics
Catalog Number
329740010
Lot Number
A0381921
Copyright
Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
H1000
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
H1000
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Acros Organics
Catalog Number
329740010
Lot Number
A0381921
Copyright
Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Catalog Number
H1000
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 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 Human Metabolite Information

8.1.1 Tissue Locations

  • Adipose Tissue
  • Placenta
  • Prostate
  • Skeletal Muscle

8.1.2 Cellular Locations

  • Cytoplasm
  • Extracellular
  • Membrane

9 Use and Manufacturing

9.1 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

9.1.1 Use Classification

EPA Safer Chemical Functional Use Classes -> Surfactants
Safer Chemical Classes -> Green circle Green circle - The chemical has been verified to be of low concern

9.1.2 Industry Uses

  • Lubricants and lubricant additives
  • Adhesives and sealant chemicals
  • Finishing agents
  • Agricultural chemicals (non-pesticidal)
  • Surface active agents

9.1.3 Consumer Uses

  • Agricultural chemicals (non-pesticidal)
  • Adhesives and sealant chemicals

9.2 U.S. Production

Aggregated Product Volume

2019: 1,000,000 lb - <20,000,000 lb

2018: 1,000,000 lb - <20,000,000 lb

2017: 1,000,000 lb - <20,000,000 lb

2016: 1,000,000 lb - <20,000,000 lb

9.3 General Manufacturing Information

Industry Processing Sectors
  • Paper Manufacturing
  • Plastics Product Manufacturing
  • All Other Basic Organic Chemical Manufacturing
  • Food, beverage, and tobacco product manufacturing
  • Miscellaneous Manufacturing
EPA TSCA Commercial Activity Status
Heptadecanoic acid: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
Pictograms displayed are for 52.1% (73 of 140) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 47.9% (67 of 140) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (52.1%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (52.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (41.4%): 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 140 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 67 of 140 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 6 notifications provided by 73 of 140 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 (52.1%)

Eye Irrit. 2A (52.1%)

STOT SE 3 (41.4%)

10.1.3 EPA Safer Chemical

Chemical: Heptadecanoic acid

Green circle Green circle - The chemical has been verified to be of low concern based on experimental and modeled data.

10.1.4 Hazards Summary

Causes convulsions in intravenous lethal-dose studies of mice (LD50 = 36 mg/kg); [RTECS] A skin and strong eye irritant; [Sigma-Aldrich MSDS]

10.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Heptadecanoic acid
REACH Restricted Substance

Restricted substance: Lead(2+) heptadecanoate

EC: 264-123-3

Restriction condition document: PDF link

New Zealand EPA Inventory of Chemical Status
Heptadecanoic acid: Does not have an individual approval but may be used under an appropriate group standard

10.3 Other Safety Information

Chemical Assessment

IMAP assessments - Heptadecanoic acid: Human health tier I assessment

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

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

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

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

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
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 EPA Safer Choice

18.6 ChemIDplus

18.7 UN GHS Classification

18.8 EPA CPDat Classification

18.9 NORMAN Suspect List Exchange Classification

18.10 CCSBase Classification

18.11 EPA DSSTox Classification

18.12 The Natural Products Atlas Classification

18.13 EPA TSCA and CDR Classification

18.14 LOTUS Tree

18.15 EPA Substance Registry Services Tree

18.16 CCS Classification - Baker Lab

18.17 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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  5. EPA Chemical Data Reporting (CDR)
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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)
    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. Baker Lab, Chemistry Department, The University of North Carolina at Chapel Hill
    FA 17:0a
    CCS Classification - Baker Lab
    https://tarheels.live/bakerlab/
  13. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  14. 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/
    FA (17:0)
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  15. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  16. ChEBI
  17. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  18. 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/
  19. 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
  20. Yeast Metabolome Database (YMDB)
    LICENSE
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    http://www.ymdb.ca/downloads
  21. 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
  22. Comparative Toxicogenomics Database (CTD)
    LICENSE
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    http://ctdbase.org/about/legal.jsp
  23. KNApSAcK Species-Metabolite Database
  24. Natural Product Activity and Species Source (NPASS)
  25. The Natural Products Atlas
    LICENSE
    The Natural Products Atlas is licensed under a Creative Commons Attribution 4.0 International License.
    https://www.npatlas.org/terms
    The Natural Products Atlas Classification
    https://www.npatlas.org/
  26. West Coast Metabolomics Center-UC Davis
    FA 17:0; (margaric acid)
  27. EPA Chemical and Products Database (CPDat)
  28. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). 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://haz-map.com/About
  29. EPA Safer Choice
    EPA Safer Chemical Ingredients Classification
    https://www.epa.gov/saferchoice
  30. FooDB
    LICENSE
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    https://foodb.ca/about
  31. MassBank Europe
  32. 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
  33. 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
  34. SpectraBase
  35. Japan Chemical Substance Dictionary (Nikkaji)
  36. Metabolomics Workbench
  37. Nature Chemical Biology
  38. Protein Data Bank in Europe (PDBe)
  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. 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/
  44. Wikidata
  45. Wikipedia
  46. PubChem
  47. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  48. GHS Classification (UNECE)
  49. EPA Substance Registry Services
  50. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  51. PATENTSCOPE (WIPO)
  52. NCBI
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