20-Hydroxycholesterol
PubChem CID
121935
Structure
Molecular Formula
Synonyms
- 20-hydroxycholesterol
- 20(S)-hydroxycholesterol
- 516-72-3
- 20alpha-Hydroxycholesterol
- (20S)-20-Hydroxycholesterol
Molecular Weight
402.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-08-08
- Modify:2025-01-18
Description
20-hydroxycholesterol is an oxysterol that is cholesterol substituted by a hydroxy group at position 20. It has a role as a human metabolite and a mouse metabolite. It is a 20-hydroxy steroid, an oxysterol and a 3beta-hydroxy-Delta(5)-steroid.
20-Hydroxycholesterol has been reported in Bombyx mori and Homo sapiens with data available.
Chemical Structure Depiction
(3S,8S,9S,10R,13S,14S,17S)-17-[(2S)-2-hydroxy-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/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
MCKLJFJEQRYRQT-APGJSSKUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CC(C)CCC[C@@](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)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C27H46O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)
17364-43-1
- (20S)-20-hydroxycholesterol
- (20S)-cholest-5-ene-3 beta,20-diol
- 20 alpha-hydroxycholesterol
- 20-hydroxycholesterol
- 20-hydroxycholesterol, (3beta,20 xi)-isomer
- 20-hydroxycholesterol, 3H-labeled, (3beta,20 xi)-isomer
- 20alpha-hydroxycholesterol
- 20R-hydroxycholesterol
- 20-hydroxycholesterol
- 20(S)-hydroxycholesterol
- 516-72-3
- 20alpha-Hydroxycholesterol
- (20S)-20-Hydroxycholesterol
- 20alpha-hydroxy cholesterol
- 20?-Hydroxy Cholesterol
- (3S,8S,9S,10R,13S,14S,17S)-17-[(2S)-2-hydroxy-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
- cholest-5-en-3beta,20-diol
- CHEBI:1296
- 30060WAL99
- (3alpha,8alpha)-Cholest-5-Ene-3,20-Diol
- 20S-hydroxycholesterol
- UNII-30060WAL99
- Cholest-5-ene-3beta,20alpha-diol
- HCD
- 20S-Cholest-5-ene-3beta,20-diol
- (20S)-Cholest-5-ene-3beta,20-diol
- Cholest-5-ene-3,20-diol, (3.beta.)-
- SCHEMBL288274
- nat-20(S)-Hydroxycholesterol
- 20 alpha -Hydroxy Cholesterol
- CHEMBL173898
- cholest-5-ene-3beta,20-diol
- BDBM20175
- DTXSID70862096
- 5-Cholestene-3beta,20alpha-diol
- MCKLJFJEQRYRQT-APGJSSKUSA-N
- 3beta-Cholest-5-ene-3,20-diol
- Cholest-5-en-3beta,20alpha-diol
- (3beta)-cholest-5-ene-3,20-diol
- 20.ALPHA.-HYDROXYCHOLESTEROL
- HY-12316R
- LMST01010201
- MFCD16661190
- 20(S)-Hydroxycholesterol (Standard)
- AKOS040732269
- Cholest-5-ene-3,20-diol, (3beta)-
- DA-49337
- HY-12316
- PD053694
- Cholest-5-ene-3beta,20-diol, (20S)-
- CS-0011056
- 20alpha-Hydroxycholesterol, analytical standard
- 20S-CHOLEST-5-ENE-3.BETA.,20-DIOL
- C05500
- CHOLEST-5-ENE-3.BETA.,20.ALPHA.-DIOL
- CHOLEST-5-ENE-3.BETA.,20-DIOL, (20S)-
- Q27067423
- (1S,2R,5S,10S,11S,14S,15S)-14-[(2S)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-7-en-5-ol
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
402.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
6.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
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
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
402.349780706 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
402.349780706 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
40.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
29
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
638
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
8
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)
Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
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 Isotope Count
Same Parent, Connectivity Count
Same Parent, Isotope Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
New Zealand EPA Inventory of Chemical Status
Cholest-5-ene-3,20-diol, (3.beta.)-: Does not have an individual approval but may be used under an appropriate group standard
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=MCKLJFJEQRYRQT-APGJSSKUSA-N
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
- BindingDBLICENSEAll data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).https://www.bindingdb.org/rwd/bind/info.jsp(1S,2R,5S,10S,11S,14S,15S)-14-[(2S)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-olhttps://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=20175
- Comparative Toxicogenomics Database (CTD)LICENSEIt 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.jsp20-hydroxycholesterolhttps://ctdbase.org/detail.go?type=chem&acc=C025813
- 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/4.0/20α-Hydroxycholesterolhttps://commonchemistry.cas.org/detail?cas_rn=516-72-3
- ChemIDplus20-Hydroxycholesterolhttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000516723ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_use20-hydroxycholesterolhttps://www.drugbank.ca/drugs/DB04704
- EPA DSSTox3beta-Cholest-5-ene-3,20-diolhttps://comptox.epa.gov/dashboard/DTXSID70862096CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- 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#linking20.ALPHA.-HYDROXYCHOLESTEROLhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/30060WAL99
- 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/Cholest-5-ene-3,20-diol, (3.beta.)-https://www.epa.govt.nz/industry-areas/hazardous-substances/guidance-for-importers-and-manufacturers/hazardous-substances-databases/
- ChEBI20-hydroxycholesterolhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:1296
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/20-Hydroxycholesterolhttps://www.wikidata.org/wiki/Q27067423LOTUS Treehttps://lotus.naturalproducts.net/
- ChEMBLLICENSEAccess 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.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- ECI Group, LCSB, University of Luxembourg20alpha-Hydroxycholesterol
- Natural Product Activity and Species Source (NPASS)20(S)-Hydroxycholesterolhttps://bidd.group/NPASS/compound.php?compoundID=NPC318495
- 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.html
- LIPID MAPSLipid Classificationhttps://www.lipidmaps.org/
- Metabolomics Workbench20S-hydroxycholesterolhttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=3443520-hydroxycholesterolhttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=3448920alpha-hydroxy cholesterolhttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=34499
- Nature Chemical Biology
- PharosLICENSEData 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/about20alpha-hydroxycholesterolhttps://pharos.nih.gov/ligands/3XQ564BDL1FS20alpha-hydroxycholesterolhttps://pharos.nih.gov/ligands/3XQCTU225RPL
- Protein Data Bank in Europe (PDBe)
- RCSB Protein Data Bank (RCSB PDB)LICENSEData 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
- SpectraBase20alpha-Hydroxycholesterolhttps://spectrabase.com/spectrum/APOG8BR1KUX20alpha-Hydroxycholesterolhttps://spectrabase.com/spectrum/BnkNFCw16EE
- Springer Nature
- Wikidata20α-hydroxycholesterolhttps://www.wikidata.org/wiki/Q27067423
- Wikipedia20S-Hydroxycholesterolhttps://en.wikipedia.org/wiki/20S-Hydroxycholesterol
- 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.html20-hydroxycholesterolhttps://www.ncbi.nlm.nih.gov/mesh/67025813
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 403601417https://pubchem.ncbi.nlm.nih.gov/substance/403601417
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