An official website of the United States government

Pyridoxal phosphate

PubChem CID
1051
Structure
Pyridoxal phosphate_small.png
Pyridoxal phosphate_3D_Structure.png
Molecular Formula
Synonyms
  • pyridoxal phosphate
  • 54-47-7
  • Codecarboxylase
  • pyridoxal 5-phosphate
  • pyridoxal 5'-phosphate
Molecular Weight
247.14 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-02-01
Description
Pyridoxal 5'-phosphate is the monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal. It has a role as a coenzyme, a human metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a mouse metabolite, an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor and a cofactor. It is a vitamin B6 phosphate, a member of methylpyridines, a monohydroxypyridine and a pyridinecarbaldehyde. It is functionally related to a pyridoxal. It is a conjugate acid of a pyridoxal 5'-phosphate(2-).
This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine).
Medicure's MC-1 drug is a cardio-protectant, designed to reduce the damage to the heart when arteries are blocked and when they are subsequently reopened after bypass surgery.
See also: Pyridoxal (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Pyridoxal phosphate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CC1=NC=C(C(=C1O)C=O)COP(=O)(O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H10NO6P
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

1071665-72-9, 52064-48-9, 52441-27-7
52441-27-7

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 NSC Number

2.3.14 PharmGKB ID

2.3.15 Pharos Ligand ID

2.3.16 Wikidata

2.3.17 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Phosphate, Pyridoxal
  • Pyridoxal 5 Phosphate
  • Pyridoxal 5-Phosphate
  • Pyridoxal P
  • Pyridoxal Phosphate
  • Pyridoxal-P

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
247.14 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
247.02457404 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
247.02457404 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
117 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
16
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
292
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

Solid

3.2.2 Melting Point

255 °C
PhysProp
255 °C

3.2.3 Solubility

Appreciable
28 mg/mL

3.2.4 LogP

-1.2

3.2.5 Dissociation Constants

3.2.6 Collision Cross Section

160.8 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

149.4 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

151.3 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

153.2 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

161.4 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

150.8 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

151.94 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

146.34 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

151.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

165.05 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

154.76 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

150.54 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

150.1 Ų [M-H]-

161.4 Ų [M+Na]+

162.4 Ų [M+Na]+

152.4 Ų [M+H]+

151.7 Ų [M+H]+

149.4 Ų [M-H]-

153.2 Ų [M-2H+Na]-

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

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

3.3.2 Cosmetics

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

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
2.50:100.00, 4.94:2.65, 5.17:23.95, 7.77:46.52, 10.43:37.85, 5.16:23.20, 4.95:2.60
Thumbnail
Thumbnail
2 of 3
View All
Spectra ID
Instrument Type
Bruker
Solvent
D2O
pH
7.4
Shifts [ppm]:Intensity
10.42:2.97, 6.24:0.50, 2.46:7.12, 7.75:2.31, 5.10:2.15, 7.74:0.59, 2.43:1.23, 5.08:2.20
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
Bruker
Solvent
D2O
pH
7.4
Shifts [ppm]:Intensity
91.47:17.37, 138.99:16.32, 154.28:49.19, 64.42:62.38, 128.87:20.84, 198.79:23.69, 18.73:100.63, 139.07:15.43, 126.77:20.06, 64.45:58.67, 198.75:12.46
Thumbnail
Thumbnail
2 of 3
View All
Copyright
Database Compilation Copyright © 2021-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 2D NMR Spectra

4.2.1 1H-1H NMR Spectra

2D NMR Spectra Type
1H-1H TOCSY
Spectra ID
Shifts [ppm] (F2:F1)
4.88:4.88, 7.76:5.11, 5.09:5.09, 7.76:5.09, 5.10:7.76, 7.76:7.76, 10.45:6.25, 2.29:2.30, 4.81:4.78, 2.17:4.83, 2.44:2.44, 4.73:5.08, 5.09:4.88, 2.46:2.47, 5.10:2.47, 9.44:4.82, 2.46:5.09, 5.20:4.82, 3.22:4.83, 4.89:4.89, 2.40:2.39, 5.09:4.82, 2.46:5.10, 6.25:10.43, 2.80:2.46, 5.42:5.08, 10.45:10.43, 6.25:6.25, 4.82:4.82, 2.62:2.63, 4.81:4.79, 3.33:4.81
Thumbnail
Thumbnail

4.2.2 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
5.10:64.42:1.00, 10.58:198.58:0.15, 10.26:198.58:0.14, 2.49:18.58:0.11, 7.75:125.98:0.66
Thumbnail
Thumbnail

4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 6
View All
Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

219.0 1

251.0 0.67

211.0 0.55

243.0 0.51

133.0 0.40

Thumbnail
Thumbnail
2 of 6
View All
Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

178.0 100

147.0 89.39

179.0 80.48

119.0 58.96

211.0 52.25

Thumbnail
Thumbnail
Notes
instrument=Leco Pegasus IV

4.3.2 MS-MS

1 of 7
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

248.0 100

150.0 68.29

122.0 3.14

168.0 3.11

94.0 1.71

Thumbnail
Thumbnail
Notes
delivery=Flow_Injectionanalyzer=Triple_Quad
2 of 7
View All
Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

94.0 100

150.0 94.86

122.0 58.83

67.0 53.04

106.0 19.80

Thumbnail
Thumbnail
Notes
delivery=Flow_Injectionanalyzer=Triple_Quad

4.3.3 LC-MS

1 of 25
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
10 V
Precursor m/z
246
Precursor Adduct
[M-H]-
Top 5 Peaks

246.3 999

164.4 80

96.9 55

228.4 14

79 11

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 25
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
20 V
Precursor m/z
246
Precursor Adduct
[M-H]-
Top 5 Peaks

164.2 999

97 922

79 181

246.1 68

146.9 63

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.3.4 Other MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
246.19
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
negative
Collision Energy
40
Top 5 Peaks
205 100
Thumbnail
Thumbnail
2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
248.22
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
positive
Collision Energy
30
Top 5 Peaks

150 100

122 15.93

94 8.84

93 6.81

149 4.32

Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

For nutritional supplementation and for treating dietary shortage or imbalance.
Investigated for use/treatment in coronary artery disease.

7.2 FDA National Drug Code Directory

7.3 Drug Labels

Active ingredient and drug

7.4 Clinical Trials

7.4.1 ClinicalTrials.gov

7.4.2 NIPH Clinical Trials Search of Japan

7.5 Biomarker Information

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Pharmacodynamics

The two major forms of vitamin B6 are pyridoxine and pyridoxamine. In the liver they are converted to pyridoxal phosphate (PLP) which is a cofactor in many reactions of amino acid metabolism. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen. Pyroluria is one potential cause of vitamin B6 deficiency.

9.2 MeSH Pharmacological Classification

Vitamin B Complex
A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)

9.3 ATC Code

A - Alimentary tract and metabolism

A11 - Vitamins

A11H - Other plain vitamin preparations

A11HA - Other plain vitamin preparations

A11HA06 - Pyridoxal phosphate

9.4 Mechanism of Action

Pyridoxal Phosphate is a coenzyme of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. Pyridoxal phosphate acts as a coenzyme in all transamination reactions, and in some oxylation and deamination reactions of amino acids. The aldehyde group of pyridoxal phosphate forms a Schiff-base linkage with the epsilon-amino group of a specific lysine group of the aminotransferase enzyme. The alpha-amino group of the amino acid substrate displaces the epsilon-amino group of the active-site lysine residue. The resulting aldimine becomes deprotonated to become a quinoid intermediate, which in turn accepts a proton at a different position to become a ketimine. Ketimine becomes hydrolyzed so that the amino group remains on the protein complex.
MC-1 is a biologically active natural product which can be regarded as a chemical entity that has been evolutionarily selected and validated for binding to particular protein domains. Thus, its underlying structural architecture, or scaffold, has already been biologically established as safe and active, providing a powerful guiding principle for novel drug and library development.

9.5 Human Metabolite Information

9.5.1 Tissue Locations

  • Erythrocyte
  • Kidney
  • Liver
  • Neuron
  • Skeletal Muscle

9.5.2 Cellular Locations

Mitochondria

9.5.3 Metabolite Pathways

9.6 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

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

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

12 Associated Disorders and Diseases

Disease
Rheumatoid arthritis
References

PubMed: 6589104, 16277678, 15338487, 10361015, 15249323

Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70: https://link.springer.com/article/10.1007/s11306-016-1000-2

Disease
Hypophosphatasia
References
Disease
Odontohypophosphatasia
References
PubMed: 23093139
Disease
Pyridoxamine 5-prime-phosphate oxidase deficiency
References
Disease
Epilepsy, early-onset, vitamin B6-dependent
References
PubMed: 27912044

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Nature Journal References

13.7 Chemical Co-Occurrences in Literature

13.8 Chemical-Gene Co-Occurrences in Literature

13.9 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15.2 Chemical-Target Interactions

15.3 Pathways

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 KEGG: Metabolite

18.4 KEGG: ATC

18.5 WHO ATC Classification System

18.6 ChemIDplus

18.7 ChEMBL Target Tree

18.8 UN GHS Classification

18.9 EPA CPDat Classification

18.10 NORMAN Suspect List Exchange Classification

18.11 CCSBase Classification

18.12 EPA DSSTox Classification

18.13 EPA TSCA and CDR Classification

18.14 LOTUS Tree

18.15 EPA Substance Registry Services Tree

18.16 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. 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/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. 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
  4. DTP/NCI
    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
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. 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
  7. 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
  8. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  9. 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/
    MAGNESIUM PYRIDOXAL 5-PHOSPHATE GLUTAMATE
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  10. ChEBI
  11. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  12. 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/
  13. 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
  14. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  15. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  16. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  17. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  18. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  19. Therapeutic Target Database (TTD)
  20. DailyMed
  21. ECI Group, LCSB, University of Luxembourg
    LICENSE
    Data: CC-BY 4.0; Code: Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    pyridoxal 5'-phosphate
  22. KNApSAcK Species-Metabolite Database
  23. Natural Product Activity and Species Source (NPASS)
  24. EPA Chemical and Products Database (CPDat)
  25. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  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. 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
  28. SpectraBase
  29. IUPAC Digitized pKa Dataset
  30. Japan Chemical Substance Dictionary (Nikkaji)
  31. 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
  32. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
    Pyridoxal 5'-phosphate
    https://markerdb.ca/chemicals/631
  33. MassBank Europe
  34. Metabolomics Workbench
  35. 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
  36. Nature Chemical Biology
  37. NIPH Clinical Trials Search of Japan
  38. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  39. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  40. Protein Data Bank in Europe (PDBe)
  41. 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
  42. Springer Nature
  43. 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/
  44. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  45. Wikidata
  46. Wikipedia
  47. Wiley
  48. 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
  49. PubChem
  50. GHS Classification (UNECE)
  51. EPA Substance Registry Services
  52. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  53. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  54. PATENTSCOPE (WIPO)
  55. NCBI
CONTENTS