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Cholestanol

PubChem CID
6665
Structure
Cholestanol_small.png
Cholestanol_3D_Structure.png
Molecular Formula
Synonyms
  • Dihydrocholesterol
  • 80-97-7
  • beta-Cholestanol
  • 5alpha-Cholestan-3beta-ol
  • CHOLESTANOL
Molecular Weight
388.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-19
  • Modify:
    2025-01-18
Description
(5alpha)-cholestan-3beta-ol is a cholestanoid that is (5alpha)-cholestane substituted by a beta-hydroxy group at position 3. It is a cholestanoid and a 3beta-hydroxy steroid. It derives from a hydride of a 5alpha-cholestane.
Dihydrocholesterol has been reported in Zea mays, Ipheion uniflorum, and other organisms with data available.
A cholesterol derivative found in human feces, gallstones, eggs, and other biological matter.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cholestanol.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

QYIXCDOBOSTCEI-QCYZZNICSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H](C4)O)C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C27H48O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

118167-50-3, 2089495-76-9, 29466-38-4, 471920-77-1
118167-50-3, 2089495-76-9, 2962807-81-2, 471920-77-1

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 Lipid Maps ID (LM_ID)

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5 alpha Cholestan 3 alpha ol
  • 5 alpha Cholestan 3 beta ol
  • 5 alpha-Cholestan-3 alpha-ol
  • 5 alpha-Cholestan-3 beta-ol
  • 5 beta Cholestan 3 beta ol
  • 5 beta-Cholestan-3 alpha-ol
  • 5 beta-Cholestan-3 beta-ol
  • beta Cholestanol
  • beta-Cholestan-3 beta-ol, 5
  • beta-Cholestanol
  • beta-ol, 5 beta-Cholestan-3
  • Cholestan 3 ol
  • Cholestan-3-ol
  • Cholestanol
  • Cholestanol, (3alpha, 5beta)-Isomer
  • Coprostanol
  • Coprosterol
  • Dihydrocholesterol

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
388.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
9.4
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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
388.370516150 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
388.370516150 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
20.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
28
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
540
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
9
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

140.0 - 142.0 °C

3.2.3 Ionization Efficiency

Ionization mode
Positive
logIE
0.04
pH
2.7
Instrument
Agilent XCT
Ion source
Electrospray ionization
Additive
formic acid (5.3nM)
Organic modifier
MeCN (80%)
Reference
DOI:

3.2.4 Collision Cross Section

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

3.3 Chemical Classes

3.3.1 Cosmetics

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

3.3.2 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

3.3.3 Lipids

Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]

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
CDCl3
pH
7.00
Shifts [ppm]:Intensity
1.05:11.33, 1.00:21.30, 0.97:16.70, 1.02:13.22, 1.52:11.58, 1.65:8.01, 1.48:9.14, 0.66:97.39, 1.55:24.51, 1.53:12.46, 1.26:25.23, 1.82:10.26, 1.66:5.37, 1.98:7.65, 1.85:3.72, 0.87:85.22, 1.00:16.95, 1.29:18.28, 1.12:26.96, 0.81:100.00, 1.81:10.11, 1.65:8.23, 0.94:11.79, 0.95:12.99, 1.69:6.33, 0.91:59.65, 1.11:23.74, 0.86:76.74, 0.87:84.09, 1.13:22.77, 1.98:5.62, 1.27:28.60, 1.28:28.06, 1.73:6.00, 1.79:8.51, 1.73:8.41, 1.99:5.22, 1.95:4.52, 1.37:21.09, 1.30:23.72, 1.64:4.87, 1.83:7.38, 1.50:9.86, 1.36:21.28, 3.59:4.72, 0.88:86.81, 1.07:15.20, 1.29:18.42, 1.14:20.59, 1.69:4.92, 1.72:6.06, 1.51:13.30, 1.25:17.39, 1.39:13.82, 1.68:7.61, 1.33:28.76, 1.84:4.73, 1.25:14.80, 1.80:9.01, 1.78:4.55, 1.81:11.13, 1.96:7.62, 0.90:57.04, 1.71:6.84, 1.04:11.33, 1.34:23.03, 1.66:5.40, 1.67:7.68, 1.47:8.52, 1.02:14.45, 1.79:10.22, 1.06:10.54, 0.97:19.89, 1.12:21.11, 0.99:15.76, 1.09:22.46, 1.58:66.68, 1.96:5.60, 1.70:9.06, 1.35:23.03
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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 2
Source of Sample
Eastman Organic Chemicals, Rochester, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Copyright
Database Compilation Copyright © 2021-2024 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
7.00
Shifts [ppm] (F2:F1):Intensity
1.07:56.13:0.15, 0.62:54.33:0.22, 1.80:31.40:0.17, 1.10:44.74:0.16, 1.55:38.21:0.20, 1.13:39.53:0.17, 0.68:12.09:0.14, 1.28:38.21:0.06, 1.40:31.61:0.12, 1.34:35.92:0.35, 1.65:32.10:0.14, 1.26:28.76:0.45, 0.90:18.62:0.53, 0.86:32.17:0.09, 1.97:39.98:0.15, 1.13:23.97:0.11, 0.98:36.47:0.08, 1.81:28.28:0.14, 1.48:21.33:0.22, 0.97:56.48:0.10, 1.22:28.35:0.12, 0.86:22.86:1.00, 1.71:37.10:0.11, 0.77:12.23:0.14, 1.55:24.18:0.16, 0.61:12.02:0.11, 1.09:39.60:0.15, 1.51:28.00:0.15, 0.84:12.23:0.21, 3.59:71.42:0.21, 1.28:21.26:0.09, 1.33:23.69:0.16
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 15
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

215.0 99.99

233.0 87.70

165.0 52.30

234.0 46.70

107.0 45.90

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Notes
instrument=SHIMADZU LKB-9000B
2 of 15
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

388.0 99.99

234.0 79.20

233.0 47.60

44.0 36.80

215.0 32.50

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Notes
instrument=JEOL JMS-01-SG-2

4.3.2 MS-MS

1 of 5
View All
Spectra ID
Instrument Type
EI-B (SHIMADZU LKB-9000B)
Ionization Mode
Positive
Top 5 Peaks

215.0 1

233.0 0.88

165.0 0.52

234.0 0.47

107.0 0.46

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2 of 5
View All
Spectra ID
Instrument Type
EI-B (JEOL JMS-01-SG-2)
Ionization Mode
Positive
Top 5 Peaks

388.0 1

234.0 0.79

233.0 0.48

44.0 0.37

215.0 0.33

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4.3.3 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+K]+
Precursor m/z
427.3336486816406
Instrument
Thermo Q Exactive HF
Instrument Type
ESI-QFT
Ionization Mode
positive
Collision Energy
65HCD
Top 5 Peaks

240.908873 100

98.975727 76.95

116.986111 63.79

222.898451 51.36

61.011358 39.44

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2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+K]+
Precursor m/z
427.3336486816406
Instrument
Thermo Q Exactive HF
Instrument Type
ESI-QFT
Ionization Mode
positive
Collision Energy
45HCD
Top 5 Peaks

306.919324 100

98.975744 90.93

59.061088 72.10

116.986105 70.23

264.908932 66.93

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4.3.4 Other MS

1 of 2
Authors
HAYASHI A, DEPT. OF CHEMISTRY, FAC. OF SCI. AND TECHNOLOGY, KINKI UNIV.
Instrument
SHIMADZU LKB-9000B
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

215 999

233 877

165 523

234 467

107 459

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License
CC BY-NC-SA
2 of 2
Authors
KOGA M, UNIV. OF OCCUPATIONAL AND ENVIRONMENTAL HEALTH
Instrument
JEOL JMS-01-SG-2
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 75 eV
Top 5 Peaks

388 999

234 792

233 476

44 368

215 325

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License
CC BY-NC-SA

4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Technique
KBr0
Source of Spectrum
Forensic Spectral Research
Source of Sample
Matheson Coleman & Bell Laboratory Chemicals
Catalog Number
8599
Lot Number
CX1525
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
FILM (CAST FROM CHCl3)
Source of Sample
EASTMAN ORGANIC CHEMICALS, ROCHESTER, NEW YORK
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Matheson Coleman & Bell Laboratory Chemicals
Catalog Number
8599
Lot Number
CX1525
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Sigma-Aldrich Company Llc.
Catalog Number
D6128
Lot Number
030M1686V
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.3 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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4.5 Raman Spectra

1 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Matheson Coleman & Bell Laboratory Chemicals
Catalog Number
8599
Lot Number
CX1525
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
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
D6128
Lot Number
030M1686V
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 Biomarker Information

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Human Metabolite Information

9.1.1 Tissue Locations

  • Brain
  • Eye Lens
  • Fibroblasts
  • Liver

9.1.2 Cellular Locations

  • Extracellular
  • Membrane

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

10.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Cholestan-3-ol, (3.beta.,5.alpha.)-: INACTIVE

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

12 Associated Disorders and Diseases

Disease
Cerebrotendinous xanthomatosis
References
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

15.2 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

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 LIPID MAPS Classification

18.4 ChemIDplus

18.5 ChEMBL Target Tree

18.6 UN GHS Classification

18.7 EPA CPDat Classification

18.8 NORMAN Suspect List Exchange Classification

18.9 CCSBase Classification

18.10 EPA DSSTox Classification

18.11 EPA TSCA and CDR Classification

18.12 LOTUS Tree

18.13 EPA Substance Registry Services Tree

18.14 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. EPA Chemicals under the TSCA
    Cholestan-3-ol, (3.beta.,5.alpha.)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  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)
    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. ChEBI
  10. 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/
  11. 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
  12. 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
  13. 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/
  14. EPA Chemical and Products Database (CPDat)
  15. 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
  16. 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
  17. 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
  18. SpectraBase
  19. Japan Chemical Substance Dictionary (Nikkaji)
  20. Kruve Lab, Ionization & Mass Spectrometry, Stockholm University
    5-alpha-cholestan-3-beta-ol
  21. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  22. Natural Product Activity and Species Source (NPASS)
    (3S,5S,10S,13R,17R)-17-((R)-1,5-Dimethyl-Hexyl)-10,13-Dimethyl-Hexadecahydro-Cyclopenta[A]Phenanthren-3-Ol
    https://bidd.group/NPASS/compound.php?compoundID=NPC71460
  23. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  24. MassBank Europe
  25. Metabolomics Workbench
  26. Nature Chemical Biology
  27. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  28. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  29. Springer Nature
  30. 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/
  31. Wikidata
  32. 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
  33. PubChem
  34. GHS Classification (UNECE)
  35. EPA Substance Registry Services
  36. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  37. PATENTSCOPE (WIPO)
  38. NCBI
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