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Androstanedione

PubChem CID
222865
Structure
Androstanedione_small.png
Androstanedione_3D_Structure.png
Molecular Formula
Synonyms
  • Androstanedione
  • 846-46-8
  • 5alpha-Androstane-3,17-dione
  • 5alpha-Androstan-3,17-dione
  • 5a-Androstanedione
Molecular Weight
288.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-04
Description
5alpha-androstane-3,17-dione is the 5alpha-stereoisomer of androstane-3,17-dione. It has a role as a mouse metabolite. It is a 3-oxo-5alpha-steroid and an androstane-3,17-dione.
Androstanedione has been reported in Arabidopsis thaliana and Homo sapiens with data available.
Androstanedione is a steroid hormone that is a mixture of alpha and beta isomers, which have different orientations for the hydrogen group at position 5. 5alpha-androstanedione is a metabolic precursor for both testosterone and estrone.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Androstanedione.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RAJWOBJTTGJROA-WZNAKSSCSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C19H28O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

358657-76-8

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 NSC Number

2.3.16 Pharos Ligand ID

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3,17-dioxy-5 alpha-androstane
  • 5 alpha-androstane-3,17-dione
  • 5 alpha-androstanedione
  • 5 beta-androstane-3,17-dione
  • androstane-3,17-dione
  • androstane-3,17-dione, (2-3(H)-labeled, (2alpha,5beta))-isomer
  • androstane-3,17-dione, (2-3(H)-labeled, (2beta,5beta))-isomer
  • androstane-3,17-dione, (4-(3)H-labeled, (4alpha,5beta))-isomer
  • androstane-3,17-dione, (4-(3)H-labeled, (4beta,5beta))-isomer
  • androstane-3,17-dione, (5alpha)-isomer
  • androstane-3,17-dione, (5beta)-isomer

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
288.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.6
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
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
288.208930132 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
288.208930132 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
34.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
21
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
496
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
6
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

133.5 - 134.0 °C

3.2.3 Collision Cross Section

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

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

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

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

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

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

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

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

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

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] -> C19 steroids (androgens) and derivatives [ST0202]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
CDCl3
pH
7.00
Shifts [ppm]:Intensity
2.29:13.83, 1.33:6.15, 1.98:3.99, 2.03:5.61, 1.01:5.90, 1.38:15.83, 1.82:6.05, 2.14:8.56, 1.60:8.43, 1.95:5.19, 1.59:4.65, 2.33:8.32, 0.81:7.81, 1.30:11.86, 2.47:7.00, 1.94:4.22, 2.41:6.06, 1.35:7.64, 1.44:8.17, 1.71:3.20, 2.07:8.24, 1.51:4.69, 1.97:4.53, 1.87:5.94, 1.65:1.90, 1.64:1.82, 1.53:9.70, 2.30:3.68, 1.71:2.91, 2.04:4.82, 1.86:10.15, 2.05:5.25, 1.28:11.10, 1.41:16.05, 1.03:6.89, 1.37:14.52, 1.93:3.58, 2.31:3.71, 1.43:7.55, 1.69:6.12, 1.57:26.48, 1.51:5.40, 1.00:5.39, 1.84:7.53, 1.27:13.29, 1.55:6.37, 0.83:7.02, 1.05:100.00, 1.73:4.85, 2.39:6.33, 2.13:9.52, 1.32:7.00, 1.96:5.55, 2.34:7.70, 1.63:5.44, 1.61:7.20, 1.26:5.63, 2.09:8.41, 1.72:5.06, 1.35:8.27, 2.10:5.50, 2.49:6.42, 1.70:6.14, 2.42:3.29, 1.31:11.44, 2.37:6.25, 1.83:10.78, 0.90:99.61, 2.26:10.33, 2.38:6.16, 1.62:5.42, 1.54:5.85, 2.32:8.02, 2.43:9.85, 2.31:4.34, 1.26:6.16, 1.85:8.24, 2.11:14.40, 1.83:11.41, 1.40:16.98, 2.34:7.32, 2.02:4.76, 1.40:11.88, 1.55:7.84, 0.99:2.16, 1.25:4.69, 2.45:8.23, 2.14:6.63, 2.02:5.25, 1.29:11.17, 1.42:5.43, 2.03:5.71, 2.05:9.88, 0.98:1.78, 1.53:3.80, 1.85:10.29, 1.96:3.97
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2 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
M. L. Lewbart, Crozer-Chester Medical Center Chester, Pennsylvania
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. 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
7.00
Shifts [ppm] (F2:F1):Intensity
1.96:21.70:0.47, 1.04:11.50:0.41, 1.71:20.68:0.76, 1.55:46.67:0.43, 1.40:28.47:1.00, 1.52:21.77:0.48, 1.01:30.51:0.41, 2.12:44.49:0.70, 2.08:35.89:0.35, 1.41:20.75:0.29, 1.83:31.31:0.41, 1.29:51.26:0.91, 2.32:38.01:0.63, 0.81:53.88:0.82, 2.39:38.08:0.54, 1.37:38.37:0.91, 2.45:35.75:0.37, 1.84:30.51:0.58, 1.27:31.31:0.45, 1.61:34.87:0.68, 2.04:38.37:0.90, 2.28:44.27:0.29, 0.89:13.76:0.27
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4.3 Mass Spectrometry

4.3.1 GC-MS

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

288.0 99.99

244.0 39.91

217.0 36.41

124.0 24.28

289.0 20.61

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Notes
instrument=HITACHI M-80
2 of 11
View All
Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

79.0 1

315.0 0.79

91.0 0.72

77.0 0.59

82.0 0.46

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4.3.2 MS-MS

1 of 6
View All
Spectra ID
Instrument Type
Linear Ion Trap
Ionization Mode
negative
Top 5 Peaks

257.219202 30.77

269.232286 18.83

243.171851 13.36

283.260877 11.01

259.225002 10.55

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Notes
instrument=Thermo Finnigan LTQ
2 of 6
View All
Spectra ID
Instrument Type
Linear Ion Trap
Ionization Mode
positive
Top 5 Peaks

266.201009 84.65

287.762462 16.01

294.216088 8.81

293.013262 8.68

265.156007 8.66

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Notes
instrument=Thermo Finnigan LTQ

4.3.3 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+Na]+
Precursor m/z
311.1981506347656
Instrument
Thermo Q Exactive HF
Instrument Type
ESI-QFT
Ionization Mode
positive
Collision Energy
65HCD
Top 5 Peaks

98.975706 100

116.986077 75.45

134.996433 26.90

59.061078 19.24

56.965503 16.98

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2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+Na]+
Precursor m/z
311.1981506347656
Instrument
Thermo Q Exactive HF
Instrument Type
ESI-QFT
Ionization Mode
positive
Collision Energy
45HCD
Top 5 Peaks

98.975698 100

194.999719 82.06

116.986069 72.29

176.989184 56.55

59.061076 42.40

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4.3.4 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
[M+H]+
Precursor m/z
289.2162066
Instrument
Agilent 6560
Ionization Mode
positive
Collision Energy
20
Retention Time
11.5988
Top 5 Peaks

253.19624 100

271.20517 79.40

197.13245 73.11

289.22867 42.72

106.08595 41.92

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2 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
[M+H]+
Precursor m/z
289.2162066
Instrument
Agilent 6560
Ionization Mode
positive
Collision Energy
40
Retention Time
11.59982
Top 5 Peaks

93.07083 100

131.08534 53.87

143.08607 53.61

95.08442 46.31

183.11618 43.70

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4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
M. L. LEWBART, CROZER-CHESTER MEDICAL CENTER, CHESTER, PENNSYLVANIA
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 0.66mg
Source of Spectrum
Forensic Spectral Research
Source of Sample
Steraloids
Catalog Number
A1630-000
Lot Number
H603
Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Steraloids Inc.
Catalog Number
A1630-000
Lot Number
H603
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Steraloids Inc.
Catalog Number
A1630-000
Lot Number
H603
Copyright
Copyright © 2013-2024 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

Testis

8.1.2 Cellular Locations

  • Endoplasmic reticulum
  • Extracellular
  • Membrane

8.1.3 Metabolite Pathways

8.2 Biochemical Reactions

8.3 Transformations

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

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Thieme References

10.5 Chemical Co-Occurrences in Literature

10.6 Chemical-Gene Co-Occurrences in Literature

10.7 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Protein Bound 3D Structures

12.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

12.2 Chemical-Target Interactions

12.3 Pathways

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

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

15 Classification

15.1 MeSH Tree

15.2 NCI Thesaurus Tree

15.3 ChEBI Ontology

15.4 LIPID MAPS Classification

15.5 KEGG: Lipid

15.6 ChemIDplus

15.7 ChEMBL Target Tree

15.8 EPA CPDat Classification

15.9 NORMAN Suspect List Exchange Classification

15.10 CCSBase Classification

15.11 EPA DSSTox Classification

15.12 LOTUS Tree

15.13 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
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    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
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  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
  7. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  9. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  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)
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    https://www.cancer.gov/policies/copyright-reuse
  13. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  14. Therapeutic Target Database (TTD)
  15. EPA Chemical and Products Database (CPDat)
  16. 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
  17. MassBank of North America (MoNA)
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    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  18. 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
    Androstane-3,17-dione, (5.alpha.)-
    http://www.nist.gov/srd/nist1a.cfm
  19. SpectraBase
  20. Japan Chemical Substance Dictionary (Nikkaji)
  21. 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
  22. KNApSAcK Species-Metabolite Database
  23. Natural Product Activity and Species Source (NPASS)
    (5S,8R,9S,10S,13S,14S)-10,13-Dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-Dodecahydro-1H-Cyclopenta[A]Phenanthrene-3,17-Dione
    https://bidd.group/NPASS/compound.php?compoundID=NPC288296
  24. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  25. Metabolomics Workbench
  26. 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/
    Androstanedione
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  27. 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
  28. Protein Data Bank in Europe (PDBe)
  29. 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
  30. Rhea - Annotated Reactions Database
    LICENSE
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    https://www.rhea-db.org/help/license-disclaimer
  31. Springer Nature
  32. SpringerMaterials
    (5S,8R,10S,13S)-10,13-Dimethyl-tetradecahydro-cyclopenta[a]phenanthrene-3,17-dione
    https://materials.springer.com/substanceprofile/docs/smsid_hmkjopmnphmfalaj
  33. 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/
  34. Wikidata
  35. Wikipedia
  36. PubChem
  37. 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
  38. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  39. PATENTSCOPE (WIPO)
  40. NCBI
CONTENTS