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Clionasterol

PubChem CID
457801
Structure
Clionasterol_small.png
Clionasterol_3D_Structure.png
Molecular Formula
Synonyms
  • Clionasterol
  • GAMMA-SITOSTEROL
  • 83-47-6
  • beta-Dihydrofucosterol
  • 22,23-Dihydroporiferasterol
Molecular Weight
414.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-01
  • Modify:
    2025-01-18
Description
Clionasterol is a member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3. It has a role as a plant metabolite and a marine metabolite. It is a 3beta-sterol, a member of phytosterols and a 3beta-hydroxy-Delta(5)-steroid. It derives from a hydride of a poriferastane.
Clionasterol has been reported in Polygala tenuifolia, Hydropuntia edulis, and other organisms with data available.
See also: Phytosterols (annotation moved to).

1 Structures

1.1 2D Structure

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

2.1.2 InChI

InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

KZJWDPNRJALLNS-FBZNIEFRSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC[C@@H](CC[C@@H](C)[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)C(C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C29H50O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

83-46-5

2.3.2 Deprecated CAS

11027-08-0, 4736-89-4, 8005-42-3

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG 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

  • 24-ethylcholest-5-en-3 beta-ol
  • 24-ethylcholesterol
  • 3beta-sitosterol
  • 3beta-stigmast-5-en-3-ol
  • beta-sitosterol
  • clionasterol
  • gamma-sitosterol
  • Harzol
  • sitosterol
  • sitosterol, (3beta)-isomer
  • sitosterol, (3beta,24xi)-isomer
  • sitosterol, 26-(14)C-labeled
  • stigmast-5-en-3-ol, (3beta,24S)-

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
414.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
9.3
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
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
414.386166214 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
414.386166214 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
30
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
634
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

147 °C

3.2.3 Kovats Retention Index

Semi-standard non-polar
3351.3 , 3290

3.3 Chemical Classes

3.3.1 Lipids

Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Stigmasterols and C24-ethyl derivatives [ST0104]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. 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 Mass Spectrometry

4.2.1 GC-MS

1 of 5
View All
NIST Number
151558
Library
Main library
Total Peaks
297
m/z Top Peak
43
m/z 2nd Highest
55
m/z 3rd Highest
57
Thumbnail
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2 of 5
View All
NIST Number
253210
Library
Replicate library
Total Peaks
152
m/z Top Peak
43
m/z 2nd Highest
55
m/z 3rd Highest
41
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 FDA National Drug Code Directory

7.2 Drug Labels

Active ingredient and drug

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Hypolipidemic Agents
Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS. (See all compounds classified as Hypolipidemic Agents.)

8.2 Human Metabolite Information

8.2.1 Cellular Locations

  • Extracellular
  • Membrane

8.3 Biochemical Reactions

9 Safety and Hazards

9.1 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Stigmast-5-en-3-ol, (3.beta.)-
New Zealand EPA Inventory of Chemical Status
Stigmast-5-en-3-ol, (3.beta.)-: Does not have an individual approval but may be used under an appropriate group standard
New Zealand EPA Inventory of Chemical Status
Stigmast-5-en-3-ol, (3.beta.,24S)-: 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.

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 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 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 ChEBI Ontology

15.3 LIPID MAPS Classification

15.4 KEGG: Metabolite

15.5 KEGG: Phytochemical Compounds

15.6 ChemIDplus

15.7 NORMAN Suspect List Exchange Classification

15.8 EPA DSSTox Classification

15.9 LOTUS Tree

15.10 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. 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/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  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. 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/
  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. 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/
  12. DailyMed
  13. Japan Chemical Substance Dictionary (Nikkaji)
  14. 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
  15. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  16. Natural Product Activity and Species Source (NPASS)
  17. Metabolomics Workbench
  18. 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
  19. 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
  20. SpectraBase
    STIGMAST-5-EN-3-OL, (3.BETA.,24S)-
    https://spectrabase.com/spectrum/C3nOrovWri2
    (24S)-24-ETHYLCHOLEST-5-EN-3-BETA-OL
    https://spectrabase.com/spectrum/9K8y84CPvIO
  21. Springer Nature
  22. Wikidata
  23. PubChem
  24. 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
  25. 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/
  26. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  27. PATENTSCOPE (WIPO)
CONTENTS