Cholesterol beta-epoxide
PubChem CID
108109
Structure
Molecular Formula
Synonyms
- 4025-59-6
- Cholesterol beta-epoxide
- 5beta,6beta-Epoxycholestan-3beta-ol
- Cholesterol 5beta,6beta-epoxide
- Cholesterol-5beta,6beta-epoxide
Molecular Weight
402.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-06-24
- Modify:2025-01-18
Description
Cholesterol beta-epoxide is 5,6beta-epoxy-5beta-cholestan-3beta-ol It is a 3beta-hydroxy steroid, an oxysterol and an epoxy steroid. It derives from a hydride of a 5beta-cholestane.
Chemical Structure Depiction
(1S,2R,5S,7S,9R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-ol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
PRYIJAGAEJZDBO-DTLXENBRSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H]4[C@]5([C@@]3(CC[C@@H](C5)O)C)O4)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C27H46O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 5,6-epoxycholesterol
- 5alpha,6alpha-epoxycholesterol
- 5beta,6beta-epoxycholesterol
- 4025-59-6
- Cholesterol beta-epoxide
- 5beta,6beta-Epoxycholestan-3beta-ol
- Cholesterol 5beta,6beta-epoxide
- Cholesterol-5beta,6beta-epoxide
- (3-beta,5-beta,6-beta)-5,6-Epoxycholestan-3-ol
- 5,6beta-epoxy-5beta-cholestan-3beta-ol
- 5beta,6beta-epoxy-cholestanol
- 5beta,6beta-epoxy-cholesterol
- PFD65A4X36
- CHEBI:28164
- 5beta,6beta-epoxy-cholestan-3beta-ol
- (1S,2R,5S,7S,9R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-ol
- (3S,4AS,5aR,6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol
- Cholestan-5beta,6beta-epoxy-3beta-ol
- CCRIS 2835
- Cholesterol 5-beta,6-beta-epoxide
- NSC 148940
- UNII-PFD65A4X36
- NSC-148940
- 5,6-Epoxy cholestanol
- 5,6beta-epoxy-cholesterol
- 5-beta-Cholestan-3-beta-ol, 5,6-beta-epoxy-
- 5Beta,6Beta-Epoxycholesterol
- SCHEMBL288394
- CHEMBL497439
- Cholestan-3-ol, 5,6-epoxy-, (3beta,5beta,6beta)-
- PRYIJAGAEJZDBO-DTLXENBRSA-
- Cholestan-3-ol, 5,6-epoxy-, (3-beta,5-beta,6-beta)-
- 5I(2),6I(2)-Epoxycholesterol
- Cholestan-3-ol, 5,6-epoxy-, (3.beta.,5.beta.,6.beta.)-
- CHOLESTEROL .BETA.-EPOXIDE
- DTXSID501314152
- 5,6.BETA.-EPOXYCHOLESTEROL
- 5beta-6beta-Epoxycholestan-3beta-ol
- LMST01010010
- MFCD00201258
- 5,beta6beta-epoxy-cholestan-3beta-ol
- Cholesterol 5 beta ,6 beta -epoxide
- 5.BETA.,6.BETA.-EPOXYCHOLESTEROL
- PD085552
- CHOLESTEROL-5.BETA.,6.BETA.-OXIDE
- 5,6-beta-epoxy-5-beta-cholestan-3-beta-ol
- CHOLESTEROL 5.BETA.,6.BETA.-EPOXIDE
- C05418
- G83424
- 5.BETA.,6.BETA.-EPOXYCHOLESTAN-3.BETA.-OL
- Q7115899
- 5,6.BETA.-EPOXY-5.BETA.-CHOLESTAN-3.BETA.-OL
- 5.BETA.-CHOLESTAN-3.BETA.-OL, 5,6.BETA.-EPOXY-
- 5beta,6beta-epoxycholestanol, cholestanol, 5beta,6beta-epoxy, powder
- InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1
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-AA
Property Value
8
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
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
32.8 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
630
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
10
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]
1D NMR Spectra
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)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=PRYIJAGAEJZDBO-DTLXENBRSA-N
- 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/4.0/5β,6β-Epoxycholesterolhttps://commonchemistry.cas.org/detail?cas_rn=4025-59-6
- ChemIDplusCholesterol beta-epoxidehttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0004025596ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSTox5β,6β-Epoxycholesterolhttps://comptox.epa.gov/dashboard/DTXSID501314152CompTox 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#linkingCHOLESTEROL .BETA.-EPOXIDEhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/PFD65A4X36
- ChEBICholesterol beta-epoxidehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28164
- 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.html
- 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 Workbench5beta,6beta-epoxy-cholesterolhttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=34370
- NMRShiftDB
- Rhea - Annotated Reactions DatabaseLICENSERhea 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
- SpectraBase(5,6-BETA)-EPOXY-5-BETA-CHOLESTAN-3-BETA-OLhttps://spectrabase.com/spectrum/49JLRVV7jxt
- Springer Nature
- Wikidatacholesterol β-epoxidehttps://www.wikidata.org/wiki/Q7115899
- 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.html5,6-epoxycholesterolhttps://www.ncbi.nlm.nih.gov/mesh/67119784
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 389785574https://pubchem.ncbi.nlm.nih.gov/substance/389785574
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