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Pregnenolone

PubChem CID
8955
Structure
Pregnenolone_small.png
Pregnenolone_3D_Structure.png
Pregnenolone__Crystal_Structure.png
Molecular Formula
Synonyms
  • pregnenolone
  • 145-13-1
  • 3beta-Hydroxypregn-5-en-20-one
  • Arthenolone
  • Pregnetan
Molecular Weight
316.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-01
  • Modify:
    2025-01-18
Description
Pregnenolone is a 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20. It has a role as a human metabolite and a mouse metabolite. It is a 20-oxo steroid, a C21-steroid and a 3beta-hydroxy-Delta(5)-steroid. It derives from a hydride of a pregnane.
A 21-carbon steroid, derived from cholesterol and found in steroid hormone-producing tissues. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids.
Pregnenolone has been reported in Abedus herberti, Locusta migratoria, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Pregnenolone.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 3
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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

1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

ORNBQBCIOKFOEO-QGVNFLHTSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H32O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

116907-59-6

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 Nikkaji Number

2.3.15 PharmGKB ID

2.3.16 Pharos Ligand ID

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5 Pregnen 3 beta ol 20 one
  • 5-Pregnen-3-beta-ol-20-one
  • Pregnenolone

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
316.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
4.2
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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
316.240230259 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
316.240230259 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
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
550
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
7
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

192 °C

3.2.3 Solubility

0.00706 mg/mL at 37 °C

3.2.4 LogP

4.22
HANSCH,C ET AL. (1995)

3.2.5 Collision Cross Section

172.95 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

178.26 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

180.92 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

174.28 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

171.8 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

175.44 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

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

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

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

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

176.1 Ų [M+H]+

214.8 Ų [M+Na]+

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

3.2.6 Kovats Retention Index

Semi-standard non-polar
2775.2

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Drugs

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

3.4.2 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

3.4.3 Lipids

Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 3
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Spectra ID
Instrument Type
JEOL
Frequency
400 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
2.17:35.00, 1.84:68.00, 1.01:633.00, 0.99:37.00, 2.30:44.00, 2.28:42.00, 1.00:35.00, 1.66:51.00, 2.13:1000.00, 2.14:38.00, 1.62:58.00, 2.30:42.00, 1.48:46.00, 1.00:37.00, 2.56:37.00, 1.66:56.00, 2.19:40.00, 2.03:33.00, 1.12:30.00, 1.88:51.00, 2.16:31.00, 1.51:67.00, 1.49:51.00, 1.66:49.00, 2.27:32.00, 1.09:34.00, 1.16:30.00, 5.35:42.00, 1.25:54.00, 5.35:43.00, 1.63:32.00, 1.60:30.00, 1.68:57.00, 2.05:38.00, 1.58:38.00, 1.46:48.00, 1.45:59.00, 1.83:46.00, 1.54:33.00, 1.03:32.00, 2.02:31.00, 1.99:165.00, 1.69:34.00, 1.67:38.00, 2.04:33.00, 1.53:63.00, 2.03:32.00, 3.53:35.00, 2.03:35.00, 2.06:40.00, 1.52:39.00, 2.54:76.00, 0.63:662.00, 2.04:47.00, 1.50:79.00, 5.34:56.00, 1.45:45.00, 1.61:39.00, 2.24:33.00, 1.84:69.00, 2.20:42.00, 0.98:37.00, 1.53:49.00, 1.19:30.00, 1.62:50.00, 1.47:126.00, 2.07:55.00, 5.36:59.00, 1.13:34.00, 1.57:30.00, 1.87:67.00, 5.34:31.00, 1.21:38.00, 1.61:40.00, 1.65:47.00, 2.24:37.00, 2.00:39.00, 1.64:41.00, 1.10:40.00, 1.17:36.00, 2.27:30.00, 2.52:33.00, 2.29:44.00, 2.17:46.00, 1.54:58.00
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Instrument Name
Varian A-60
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 3
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Spectra ID
Frequency
50.18 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
209.36:614.00, 50.11:827.00, 44.00:787.00, 31.83:879.00, 31.65:974.00, 31.94:1000.00, 13.23:901.00, 42.31:859.00, 57.00:966.00, 63.74:818.00, 140.91:699.00, 31.45:817.00, 22.95:922.00, 71.65:822.00, 38.92:897.00, 19.42:780.00, 24.53:813.00, 37.35:819.00, 121.29:818.00, 36.59:955.00, 21.14:768.00
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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 Mass Spectrometry

4.2.1 GC-MS

1 of 6
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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

316.0 99.99

283.0 76

231.0 71.30

213.0 39.10

187.0 39

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Notes
instrument=HITACHI M-52
2 of 6
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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-52
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

316 99.99

283 76

231 71.30

213 39.10

187 39

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License
CC BY-NC-SA

4.2.2 MS-MS

1 of 2
NIST Number
1006637
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
317.2475
Total Peaks
32
m/z Top Peak
281
m/z 2nd Highest
199
m/z 3rd Highest
159
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2 of 2
NIST Number
1054029
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
317.2475
Total Peaks
45
m/z Top Peak
299.3
m/z 2nd Highest
281.4
m/z 3rd Highest
273.3
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4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
E. MERCK AG, DARMSTADT, GERMANY
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bio-Rad FTS
Technique
KBr1 0.57mg
Source of Spectrum
Forensic Spectral Research
Source of Sample
Steraloids
Catalog Number
Q5500-000
Lot Number
H251
Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.2 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II) ground
Source of Spectrum
Forensic Spectral Research
Source of Sample
Steraloids Inc.
Catalog Number
Q5500-000
Lot Number
H251
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.3 Vapor Phase IR Spectra

Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 Raman Spectra

1 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Steraloids Inc.
Catalog Number
Q5500-000
Lot Number
H251
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Sigma-Aldrich Company Llc.
Catalog Number
P9129
Lot Number
061M1158V
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

7.2 FDA National Drug Code Directory

7.3 Clinical Trials

7.3.1 ClinicalTrials.gov

7.4 Biomarker Information

8 Pharmacology and Biochemistry

8.1 Metabolism / Metabolites

Pregnenolone has known human metabolites that include 1-(3,16-Dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, 2-Hydroxy-1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, and Pregn-5-en-20-on-3b-yl sulfurate.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

8.2 Human Metabolite Information

8.2.1 Tissue Locations

  • Adrenal Cortex
  • Adrenal Gland
  • Brain
  • Kidney
  • Neuron
  • Ovary
  • Placenta
  • Testis

8.2.2 Cellular Locations

  • Cytoplasm
  • Endoplasmic reticulum
  • Extracellular
  • Membrane
  • Mitochondria

8.2.3 Metabolite Pathways

8.3 Biochemical Reactions

8.4 Transformations

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Note
Pictograms displayed are for 87% (20 of 23) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 13% (3 of 23) of reports.
Pictogram(s)
Irritant
Health Hazard
Signal
Warning
GHS Hazard Statements

H302 (87%): Harmful if swallowed [Warning Acute toxicity, oral]

H312 (87%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H332 (87%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H351 (87%): Suspected of causing cancer [Warning Carcinogenicity]

H361 (87%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Precautionary Statement Codes

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, 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 23 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 3 of 23 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 2 notifications provided by 20 of 23 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.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (87%)

Acute Tox. 4 (87%)

Acute Tox. 4 (87%)

Carc. 2 (87%)

Repr. 2 (87%)

9.2 Regulatory Information

REACH Registered Substance

10 Toxicity

10.1 Toxicological Information

10.1.1 Acute Effects

11 Associated Disorders and Diseases

Disease
Premenstrual dysphoric disorder
References
PubMed: 12215085
Disease
Prepartum depression
References
PubMed: 11739473
Disease
Postpartum depression
References
PubMed: 11739473
Disease
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
References
PubMed: 18182448

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Wiley References

12.6 Nature Journal References

12.7 Chemical Co-Occurrences in Literature

12.8 Chemical-Gene Co-Occurrences in Literature

12.9 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

14.2 Chemical-Target Interactions

14.3 Drug-Drug Interactions

14.4 Pathways

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

Zebrafish Pathway Metabolite MetFrag Local CSV (Beta) | DOI:10.5281/zenodo.3457553
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 LIPID MAPS Classification

17.5 KEGG: Metabolite

17.6 KEGG: Lipid

17.7 ChemIDplus

17.8 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

17.9 ChEMBL Target Tree

17.10 UN GHS Classification

17.11 NORMAN Suspect List Exchange Classification

17.12 CCSBase Classification

17.13 EPA DSSTox Classification

17.14 LOTUS Tree

17.15 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
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    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
  6. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Human Metabolome Database (HMDB)
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    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/
    Pregnenolone
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  10. ChEBI
  11. 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/
  12. NCI Thesaurus (NCIt)
    LICENSE
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    https://www.cancer.gov/policies/copyright-reuse
  13. Open Targets
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    https://platform-docs.opentargets.org/licence
  14. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  15. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  16. 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
  17. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  18. Therapeutic Target Database (TTD)
  19. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  20. ECI Group, LCSB, University of Luxembourg
    LICENSE
    Data: CC-BY 4.0; Code: Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Pregnenolone
  21. Natural Product Activity and Species Source (NPASS)
  22. 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
  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
  24. SpectraBase
  25. Japan Chemical Substance Dictionary (Nikkaji)
  26. 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
  27. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  28. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  29. Metabolomics Workbench
  30. National Drug Code (NDC) Directory
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  31. Nature Chemical Biology
  32. PharmGKB
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    https://www.pharmgkb.org/page/policies
  33. Pharos
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    https://pharos.nih.gov/about
  34. Protein Data Bank in Europe (PDBe)
  35. RCSB Protein Data Bank (RCSB PDB)
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  36. Rhea - Annotated Reactions Database
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    https://www.rhea-db.org/help/license-disclaimer
  37. Springer Nature
  38. SpringerMaterials
    1-((3S,8S,10R,13S,17S)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone
    https://materials.springer.com/substanceprofile/docs/smsid_atjubwkftxcqmvrf
  39. The Cambridge Structural Database
  40. Thieme Chemistry
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  45. PubChem
  46. GHS Classification (UNECE)
  47. IUPHAR/BPS Guide to PHARMACOLOGY
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  48. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  49. PATENTSCOPE (WIPO)
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