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Colfosceril palmitate

PubChem CID
452110
Structure
Colfosceril palmitate_small.png
Molecular Formula
Synonyms
  • 63-89-8
  • Colfosceril palmitate
  • 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine
  • DPPC
  • diPalmitoylphosphatidylcholine
Molecular Weight
734.0 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-19
  • Modify:
    2025-01-18
Description
1,2-dihexadecanoyl-sn-glycero-3-phosphocholine is a phosphatidylcholine 32:0 in which the 1- and 2-acyl groups are specified as hexadecanoyl (palmitoyl). A synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of pulmonary surfactants. It has a role as a surfactant and a mouse metabolite. It is a phosphatidylcholine 32:0 and a 1-acyl-2-hexadecanoyl-sn-glycero-3-phosphocholine. It is functionally related to a hexadecanoic acid. It is a conjugate base of a 1,2-di-O-palmitoyl-sn-glycero-3-phosphocholine.
Colfosceril palmitate is a synthetic pulmonary surfactant administered in infants with respiratory distress syndrome. It was part of the first generation of commercially available artificial surfactants. It was developed by Burroughs Wellcome and it was FDA approved on August 6, 1990. Nowadays colfosceril palmitate is under the state of canceled post-marketing.
Colfosceril palmitate has been reported in Homo sapiens, Lycoris radiata, and Trypanosoma brucei with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Colfosceril palmitate.png

1.2 3D Status

Conformer generation is disallowed since too flexible

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R)-2,3-di(hexadecanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

KILNVBDSWZSGLL-KXQOOQHDSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C40H80NO8P
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

875249-75-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 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 RXCUI

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,2-dipalmitoyl-sn-glycero-3-phosphocholine
  • colfosceril palmitate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
734.0 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
13.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
40
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
733.56215551 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
733.56215551 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
111 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
50
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
826
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
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Boiling Point

60.5-61.5ºC at 760 mmHg
'MSDS'

3.2.3 Melting Point

-63ºC
'MSDS'

3.2.4 Solubility

Very poor solubility
Li, et al. Asian Journal of Pharmaceutical Sciences. Vol. 10. Issue 2. (2015)

3.2.5 LogP

1.97
'MSDS'

3.2.6 Collision Cross Section

285.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]

283.9 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]

289.2 Ų [M+CH3COO]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]

283.19 Ų [M+CH3COO]- [CCS Type: TIMS; Method: single field calibrated]

281.91 Ų [M+H]+ [CCS Type: TIMS; Method: single field calibrated]

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Human drug -> Active ingredient (COLFOSCERIL PALMITATE)

3.3.2 Lipids

Lipids -> Unambiguous Lipids
Lipids -> Glycerophospholipids [GP] -> Glycerophosphocholines [GP01] -> Diacylglycerophosphocholines [GP0101]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
CDCl3
pH
Not Applic
Shifts [ppm]:Intensity
4.55:0.54, 3.94:2.55, 1.01:12.55, 1.71:2.90, 5.34:1.35, 4.06:0.60, 5.36:0.42, 3.93:2.08, 3.50:32.03, 1.00:5.92, 4.46:1.27, 4.52:0.74, 2.39:2.60, 4.28:1.00, 4.24:0.89, 4.46:1.26, 1.02:5.42, 1.39:100.00, 2.42:4.67, 4.27:1.05, 2.44:2.22, 4.07:0.76, 4.08:1.40, 4.54:0.60, 4.07:0.91, 4.10:1.20, 5.35:1.31, 2.41:4.95, 1.71:3.06, 4.26:1.03, 4.09:1.23, 4.11:0.97, 5.32:0.49, 4.52:0.73
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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
7.00
Shifts [ppm] (F2:F1):Intensity
0.88:14.10:0.01, 4.29:59.43:0.06, 1.28:29.22:0.16, 3.76:66.42:0.05, 2.28:34.29:0.06, 3.33:54.38:0.31, 1.58:24.92:0.06, 1.25:31.97:0.07, 5.19:70.54:0.03, 4.12:63.04:0.02, 1.29:22.70:0.03, 4.39:62.97:0.01, 1.25:29.75:1.00, 3.92:63.45:0.02
Thumbnail
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4.3 Mass Spectrometry

4.3.1 MS-MS

1 of 7
View All
Spectra ID
Instrument Type
IT
Ionization Mode
negative
Top 5 Peaks

255.0 40.12

718.0 39.71

768.0 12.35

481.0 6.24

462.0 1.17

Thumbnail
Thumbnail
Notes
adduct_type [M+Cl]- original_collision_energy 40 CannabisDB spectra from NIST14 2020 June ABI 4000 QTRAP
2 of 7
View All
Spectra ID
Instrument Type
QqQ
Ionization Mode
positive
Top 5 Peaks

184.0 96.67

735.0 1.66

86.0 1.66

Thumbnail
Thumbnail
Notes
adduct_type [M+H]+ original_collision_energy -1 nominal CannabisDB spectra from NIST14 2020 June Finnigan MAT TSQ 7000

4.3.2 LC-MS

1 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+HAc-H]-
Precursor m/z
792.575
Instrument
qTof
Ionization Mode
negative
Top 5 Peaks

255.231750 100

718.536804 88.24

719.541931 43.80

716.577026 21.89

256.234222 15.09

Thumbnail
Thumbnail
2 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-CH3]-
Precursor m/z
718.537
Instrument
qTof
Ionization Mode
negative
Top 5 Peaks

303.232788 100

722.511230 48.77

723.514832 20.67

304.236115 19.88

436.282593 14.59

Thumbnail
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Colfosceril palmitate is indicated for the treatment of respiratory distress syndrome (RDS) in premature infants. The official label is referred as a intratracheal suspension for prophylactic treatment of infants of less than 1350 grams of birth weight under risk of developing RDS, or in infants with birth weight greater than 1350 grams with pulmonary immaturity, or as rescue treatment of infants that already developed RDS. The central feature of RDS is a surfactant deficiency due to lung immaturity. This lung condition is more frequently presented due to risk factors like prematurity, delayed lung maturation caused by maternal diabetes or male gender, or surfactant dysfuntion due to perinatal asphyxia, pulmonary infection or delivery without labor.

7.2 FDA Approved Drugs

7.3 FDA Orange Book

7.4 Clinical Trials

7.4.1 EU Clinical Trials Register

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Pharmacodynamics

Colfosceril palmitate has shown to significantly reduce the risk of pneumothoraces, pulmonary interstitial emphysema and mortality. Unlike naturals surfactants, colfosceril palmitate reduces the risk of bronchopulmonary dysplasia, intraventricular hemorrhage and patent ductus arteriosus. In clinical placebo-controlled trials, there was a significant reduction in the number of deaths attributed to hyaline membrane disease, the incidence of pulmonary air leaks, oxygen requirements and mean airway pressure. Some reports have indicated a lack of therapeutic effect due to the absence of surfactant protein.

9.2 ATC Code

R - Respiratory system

R07 - Other respiratory system products

R07A - Other respiratory system products

R07AA - Lung surfactants

R07AA01 - Colfosceril palmitate

9.3 Absorption, Distribution and Excretion

Absorption
The absorption is done directly in the alveolus into the lung tissue. As the lung surfactant is distributed in the bronchi, bronchioles and alveoli, its highest concentration is at the alveolar air-fluid interface where it remains as a monolayer.
Route of Elimination
After 5 days, most of the administered dose (56%) is distributed throughout the body with renal and fecal excretion being the minor elimination pathway representing the 4 and 2% of the eliminated dose respectively. The major route of elimination is by expelled air which accounts for 28% of the administered dose.
Volume of Distribution
Colfosceril palmitate is distributed uniformly to all lobes of the lung, distal airways and alveolar spaces. It will not enter the systemic circulation in healthy lungs, however when the integrity of the tissue is distrupted colfosceril can reach systemic circulation. Even 5 days after administration, there are traces of colfosceril palmitate retained in the body that represented 72% of the administered dose which by then have entered pathways of lipid metabolism to become tissue associated.
Clearance
After 5 days of drug administration, the lung and liver would contain 10% of the administered dose and the elimination via renal excretion accounts only for 8% of the administered dose. This proved a very small renal clearance and confirmed that the major elimination route is by expired air.

9.4 Metabolism / Metabolites

Colfosceril palmitate is catabolized and reutilized for further synthesis and secretion in lung tissues.

9.5 Biological Half-Life

The half-life of colfosceril palmitate is registered to be in the range of 20-36 hours.

9.6 Mechanism of Action

Treatment with colfosceril palmitate aims to reinflate a collapsed area of the lung, improve compliance and reduce intrapulmonary shunting. The actions of colfosceril palmitate are perfomed by replacing the defficient or innefective endogenous lung surfactant and thus, reducing the tension and stabilizing the alveoli from collapsing. Colfosceril palmitate will form a very thin film that will cover the surface of the alveolar cells and therefore it will reduce surface tension.

9.7 Human Metabolite Information

9.7.1 Tissue Locations

Placenta

9.7.2 Cellular Locations

  • Cytoplasm
  • Extracellular
  • Membrane

9.7.3 Metabolite Pathways

9.8 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

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.

11.1.2 Hazard Classes and Categories

Not Classified

11.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Colfosceril palmitate: 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 Toxicity

12.1 Toxicological Information

12.1.1 Protein Binding

Colfosceril palmitate stays and gets metabolized in the pulmunar tissue, thus it is not able to bind to plasma proteins.

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.

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

Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Wiley References

14.5 Nature Journal 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

16.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

16.2 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 LIPID MAPS Classification

19.5 KEGG: ATC

19.6 WHO ATC Classification System

19.7 ChemIDplus

19.8 ChEMBL Target Tree

19.9 UN GHS Classification

19.10 EPA CPDat Classification

19.11 CCSBase Classification

19.12 EPA DSSTox Classification

19.13 LOTUS Tree

19.14 CCS Classification - Baker Lab

19.15 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. Baker Lab, Chemistry Department, The University of North Carolina at Chapel Hill
    PC(16:0/16:0)
    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/
    1,2-Dipalmitoyl-sn-glycero-3-phosphocholine
    https://commonchemistry.cas.org/detail?cas_rn=63-89-8
  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
    (R)-(4-oxido-10-oxo-7-palmitoyl-3,5,9-trioxa-4-phosphapentacosyl)trimethylammonium 4-oxide
    https://echa.europa.eu/substance-information/-/substanceinfo/100.000.516
    (R)-(4-oxido-10-oxo-7-palmitoyl-3,5,9-trioxa-4-phosphapentacosyl)trimethylammonium 4-oxide (EC: 200-567-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/65162
  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
    1,2-dihexadecanoyl-sn-glycero-3-phosphocholine
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:72999
  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
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    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. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  17. 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
  18. Drugs@FDA
    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
  19. EPA Chemical and Products Database (CPDat)
  20. EU Clinical Trials Register
  21. FDA Orange Book
    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
  22. FooDB
    LICENSE
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    https://foodb.ca/about
  23. 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
    1,2-Dihexadecanoyl-sn-glycero-3-phosphocholine
    http://www.nist.gov/srd/nist1a.cfm
  24. 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
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  25. Natural Product Activity and Species Source (NPASS)
  26. 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
  27. Metabolomics Workbench
  28. Nature Chemistry
  29. 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
  30. Therapeutic Target Database (TTD)
  31. Protein Data Bank in Europe (PDBe)
  32. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
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    https://www.rcsb.org/pages/policies
  33. Rhea - Annotated Reactions Database
    LICENSE
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    https://www.rhea-db.org/help/license-disclaimer
  34. Springer Nature
  35. WHO Anatomical Therapeutic Chemical (ATC) Classification
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    https://www.whocc.no/copyright_disclaimer/
  36. Wikidata
  37. Wikipedia
  38. Wiley
  39. PubChem
  40. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  41. GHS Classification (UNECE)
  42. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  43. PATENTSCOPE (WIPO)
  44. NCBI
CONTENTS