Clionasterol
PubChem CID
457801
Structure
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).
Chemical Structure Depiction
(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)
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)
KZJWDPNRJALLNS-FBZNIEFRSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
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)
C29H50O
Computed by PubChem 2.2 (PubChem release 2021.10.14)
83-46-5
11027-08-0, 4736-89-4, 8005-42-3
- 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)-
- Clionasterol
- GAMMA-SITOSTEROL
- 83-47-6
- beta-Dihydrofucosterol
- 22,23-Dihydroporiferasterol
- Poriferast-5-en-3beta-ol
- (3beta,24S)-Stigmast-5-en-3-ol
- .gamma.-Sitosterol
- 24beta-Ethylcholesterol
- .beta.-Dihydrofucosterol
- 24.beta.-Ethylcholesterol
- Fucosterol, .beta.-dihydro-
- Stigmast-5-en-3-ol, (3.beta.,24S)-
- 5LI01C78DD
- 24-ethylcholest-5-en-3 beta-ol
- 24S-Ethylcholest-5-en-3.beta.-ol
- Stigmast-5-en-3.beta.-ol, (24S)-
- (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
- .beta.-Sitosterin
- .beta.-Sitosterol
- 5-Stigmasten-3beta-ol
- 24.alpha.-Ethylcholesterol
- Stigmast-5-en-3.beta.-ol
- UNII-5LI01C78DD
- g-Sitosterol
- Stigmast-5-en-3-ol, (3.beta.)-
- b-Dihydrofucosterol
- EINECS 201-481-1
- 24b-Ethylcholesterol
- Stigmast-5-en-3-ol, (3beta,24S)-
- bmse000477
- SCHEMBL219424
- 24b-Ethylcholest-5-en-3b-ol
- 24S-Ethylcholest-5-en-3b-ol
- .GAMMA.-SITOSTEROL [MI]
- (24S)-stigmast-5-en-3beta-ol
- 24S-Ethylcholest-5-en-3beta-ol
- CHEBI:132823
- KZJWDPNRJALLNS-FBZNIEFRSA-N
- DTXSID801015721
- 24beta-Ethyl-5-cholesten-3beta-ol
- LMST01040122
- AKOS025401337
- 24.beta.-Ethyl-5-cholesten-3.beta.-ol
- AC-11107
- AC-34227
- (24S)-STIGMAST-5-EN-3.BETA.-OL
- NS00076592
- (3.BETA.,24S)-STIGMAST-5-EN-3-OL
- C19654
- 24.BETA.-ETHYLCHOLEST-5-EN-3.BETA.-OL
- Q27262523
- 8295076E-C876-4B41-ADF5-02A644EEA34F
Property Name
Property Value
Reference
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)
Solid
147 °C
Semi-standard non-polar
3351.3 , 3290
Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Stigmasterols and C24-ethyl derivatives [ST0104]
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
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
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Phytosterols (annotation moved to)
PubMed Count
Active ingredient and drug
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.)
- Extracellular
- Membrane
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.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=KZJWDPNRJALLNS-FBZNIEFRSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- Australian Industrial Chemicals Introduction Scheme (AICIS)Stigmast-5-en-3-ol, (3.beta.)-https://services.industrialchemicals.gov.au/search-inventory/
- CAS Common ChemistryLICENSEThe 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/
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSToxgamma-Sitosterolhttps://comptox.epa.gov/dashboard/DTXSID801015721CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- European Chemicals Agency (ECHA)LICENSEUse 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(3β,24S)-stigmast-5-en-3-olhttps://echa.europa.eu/substance-information/-/substanceinfo/100.001.347
- FDA Global Substance Registration System (GSRS)LICENSEUnless 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.GAMMA.-SITOSTEROLhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/5LI01C78DD
- Human Metabolome Database (HMDB)LICENSEHMDB 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/citingClionasterolhttp://www.hmdb.ca/metabolites/HMDB0000649
- New Zealand Environmental Protection Authority (EPA)LICENSEThis work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.https://www.epa.govt.nz/about-this-site/general-copyright-statement/
- ChEBI
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Clionasterolhttps://www.wikidata.org/wiki/Q27262523LOTUS Treehttps://lotus.naturalproducts.net/
- Crystallography Open Database (COD)LICENSEAll 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/
- DailyMed
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlCompounds with biological roleshttp://www.genome.jp/kegg-bin/get_htext?br08001.kegPhytochemical compoundshttp://www.genome.jp/kegg-bin/get_htext?br08003.keg
- LIPID MAPSLipid Classificationhttps://www.lipidmaps.org/
- Natural Product Activity and Species Source (NPASS)
- Metabolomics Workbench
- National Drug Code (NDC) DirectoryLICENSEUnless 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
- NIST Mass Spectrometry Data CenterLICENSEData covered by the Standard Reference Data Act of 1968 as amended.https://www.nist.gov/srd/public-law.gamma.-Sitosterolhttp://www.nist.gov/srd/nist1a.cfm
- SpectraBasegamma-sitosterolhttps://spectrabase.com/spectrum/6M2uCcoDjueSTIGMAST-5-EN-3-OL, (3.BETA.,24S)-https://spectrabase.com/spectrum/C3nOrovWri2BETA-SITOSTEROLhttps://spectrabase.com/spectrum/ElXMPcwjwR1(24S)-24-ETHYLCHOLEST-5-EN-3-BETA-OLhttps://spectrabase.com/spectrum/9K8y84CPvIO
- Springer Nature
- Wikidataγ-sitosterolhttps://www.wikidata.org/wiki/Q27262523
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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.htmlgamma-sitosterolhttps://www.ncbi.nlm.nih.gov/mesh/67025473Hypolipidemic Agentshttps://www.ncbi.nlm.nih.gov/mesh/68000960
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/NORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 403430134https://pubchem.ncbi.nlm.nih.gov/substance/403430134
CONTENTS