Page last updated: 2024-12-08

cholesterol alpha-oxide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

cholesterol alpha-oxide: RN given refers to (3beta,5alpha,6alpha)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID227037
CHEMBL ID497438
CHEBI ID49305
SCHEMBL ID289077
MeSH IDM0042986

Synonyms (63)

Synonym
unii-3uq9pf5xbd
5-17-04-00143 (beilstein handbook reference)
3uq9pf5xbd ,
5-alpha-cholestan-3-beta-ol, 5,6-alpha-epoxy-
cholesterol 5-alpha,6-alpha-epoxide
5alpha,6alpha-epoxycholestan-3beta-ol
cholestan-3beta-ol, 5alpha,6alpha-epoxy-
cholesterol-alpha-epoxide
einecs 215-007-6
ccris 880
cholestan-3-ol, 5,6-epoxy-, (3beta,5alpha,6alpha)-
cholestan-3-ol, 5,6-epoxy-, (3-beta,5-alpha,6-alpha)-
cholesterol alpha-oxide
5,6-alpha-epoxy-5-alpha-cholestan-3-beta-ol
brn 0089511
cholesterol epoxide
5-alpha,6-alpha-epoxycholestanol
cholesterol .alpha.-oxide
1250-95-9
5.alpha.,6.alpha.-epoxycholestan-3.beta.-ol
cholesterol .alpha.-epoxide
cholestan-3.beta.-ol,6.alpha.-epoxy-
cholestan-3-ol,6-epoxy-, (3.beta.,5.alpha.,6.alpha.)-
5.alpha.-cholestan-3.beta.-ol,6.alpha.-epoxy-
nsc-18176
nsc18176
5,6alpha-epoxy-cholestanol
LMST01010011
5,6alpha-epoxy-cholesterol
5alpha,6alpha-epoxy-5alpha-cholestan-3beta-ol
5,6alpha-epoxy-5alpha-cholestan-3beta-ol
cholesterol-5alpha,6alpha-epoxide
cholesterol 5alpha,6alpha-epoxide
5,6alpha epoxy-cholesterol
CHEBI:49305 ,
5alpha,6alpha-epoxycholesterol
CHEMBL497438
cholesterol alpha-epoxide
C1222
3beta-hydroxy-5alpha,6alpha-epoxycholestane
3.beta.-hydroxycholestane 5.alpha.,6.alpha.-epoxide
5,6.alpha.-epoxy-5.alpha.-cholestan-3.beta.-ol
3.beta.-hydroxy-5,6.alpha.-epoxy-5.alpha.-cholestane
AKOS025294227
SCHEMBL289077
PRYIJAGAEJZDBO-ZEQHCUNVSA-N
mfcd00046980
J-005193
(1s,2r,5s,7r,9s,11s,12s,15r,16r)-2,16-dimethyl-15-[(2r)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.0(2),?.0?,?.0(1)(2),(1)?]octadecan-5-ol
AS-64044
F17595
cholesterol 5-alfa,6-alfa-epoxide
(1s,2r,5s,7r,9s,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
Q27121609
cholesterol 5 alpha ,6 alpha -epoxide
5a,6a-epoxycholesterol
BAA25095
cholesterol-5+/-,6+/--epoxide
DTXSID101030546
CS-0136120
PD088539
cholesterol-5|a,6|a-epoxide
HY-133971

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The order of cytotoxic potency of these cholesterol oxides is: cholestane triol greater than cholesterol-beta-epoxide greater than cholesterol-alpha-epoxide, with LD50 concentrations ranging from 23 to greater than 150 microM in confluent cells."( Uptake, metabolism, and cytotoxicity of isomeric cholesterol-5,6-epoxides in rabbit aortic endothelial cells.
Berliner, J; Peterson, H; Sevanian, A, 1991
)
0.28
" Both beta-epox and alpha-epox were more toxic to HepG2 cells than to Caco-2 cells after the 48-h exposure."( Toxicity of cholesterol oxidation products to Caco-2 and HepG2 cells: modulatory effects of alpha- and gamma-tocopherol.
O'Brien, NM; O'Callaghan, YC; O'Sullivan, AJ; Woods, JA,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
3beta-hydroxy steroidA 3-hydroxy steroid in which the 3-hydroxy substituent is in the beta-position.
oxysterolAn oxygenated derivative of cholesterol
epoxy steroidAny steroid whose structure includes an epoxy group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
7-oxo-C and 7-beta-HC pathways1513
Oxysterols derived from cholesterol3831

Bioassays (11)

Assay IDTitleYearJournalArticle
AID375536Cytotoxicity against human HT-29 cells after 48 hrs by Alamar Blue assay2009Journal of medicinal chemistry, Jul-09, Volume: 52, Issue:13
Efficient chemoenzymatic synthesis, cytotoxic evaluation, and SAR of epoxysterols.
AID444826Induction of dendrite out growth in IL-4/GMCSF-stimulated mouse P19 cells assessed as dendrite length at 100 nM after 48 hrs by light microscopy2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Synthesis of new alkylaminooxysterols with potent cell differentiating activities: identification of leads for the treatment of cancer and neurodegenerative diseases.
AID444824Induction of dendrite out growth in IL-4/GMCSF-stimulated human U937 cells assessed as dendrite length at 100 nM after 48 hrs by light microscopy2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Synthesis of new alkylaminooxysterols with potent cell differentiating activities: identification of leads for the treatment of cancer and neurodegenerative diseases.
AID537061Chemical stability of the compound in 0.1 M aqueous phosphate buffer assessed as hydrolysis at pH 7.4 after 96 hrs2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Sterols as anticancer agents: synthesis of ring-B oxygenated steroids, cytotoxic profile, and comprehensive SAR analysis.
AID537065Chemical stability of the compound in 0.1 M aqueous phosphate buffer assessed as hydrolysis at pH 5.7 after 96 hrs2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Sterols as anticancer agents: synthesis of ring-B oxygenated steroids, cytotoxic profile, and comprehensive SAR analysis.
AID444823Plasma concentration healthy human2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Synthesis of new alkylaminooxysterols with potent cell differentiating activities: identification of leads for the treatment of cancer and neurodegenerative diseases.
AID537062Chemical stability of the compound in 0.1 M aqueous phosphate buffer assessed as hydrolysis at pH 6.7 after 96 hrs2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Sterols as anticancer agents: synthesis of ring-B oxygenated steroids, cytotoxic profile, and comprehensive SAR analysis.
AID537051Cytotoxicity against human HT-29 cells after 96 hrs by Alamar blue assay2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Sterols as anticancer agents: synthesis of ring-B oxygenated steroids, cytotoxic profile, and comprehensive SAR analysis.
AID444827Cytotoxicity against mouse P19 cells after 3 days by trypan blue exclusion assay2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Synthesis of new alkylaminooxysterols with potent cell differentiating activities: identification of leads for the treatment of cancer and neurodegenerative diseases.
AID444825Cytotoxicity against human U937 cells after 3 days by trypan blue exclusion assay2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Synthesis of new alkylaminooxysterols with potent cell differentiating activities: identification of leads for the treatment of cancer and neurodegenerative diseases.
AID537050Cytotoxicity against human HT-29 cells after 48 hrs by Alamar blue assay2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Sterols as anticancer agents: synthesis of ring-B oxygenated steroids, cytotoxic profile, and comprehensive SAR analysis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (71)

TimeframeStudies, This Drug (%)All Drugs %
pre-199027 (38.03)18.7374
1990's20 (28.17)18.2507
2000's13 (18.31)29.6817
2010's11 (15.49)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.94

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index9.94 (24.57)
Research Supply Index4.34 (2.92)
Research Growth Index4.28 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.94)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.33%)5.53%
Reviews5 (6.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other69 (92.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]