Page last updated: 2024-12-07

cholest-5-en-3 beta,7 alpha-diol

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

Description

7alpha-hydroxycholesterol : The 7alpha-hydroxy derivative of cholesterol. [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]

Cross-References

ID SourceID
PubMed CID107722
CHEMBL ID497207
CHEBI ID17500
SCHEMBL ID281941
MeSH IDM0058248

Synonyms (47)

Synonym
7alpha-hydroxy-cholesterol
CHEBI:17500 ,
7 alpha-hydroxycholesterol
cholest-5-en-3beta,7alpha-diol
LMST01010013
566-26-7
7alpha-hydroxycholesterol
C03594
cholest-5-ene-3beta,7alpha-diol
5-cholesten-3beta,7alpha-diol
7-hydroxycholesterol
7alpha-cholesterol
7|a-hydroxy cholesterol
CHEMBL497207
(3s,7s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-3,7-diol
unii-95d0i22i0v
7-alpha-hydroxycholesterol
95d0i22i0v ,
cholest-5-ene-3,7-diol, (3beta,7alpha)-
7|a-hydroxycholesterol
gtpl4351
7-alpha-ohc
cholest-5-ene-3,7-diol, (3.beta.,7.alpha.)-
7.alpha.-hydroxycholesterol
cholest-5-ene-3.beta.,7.alpha.-diol
7.alpha.-hydroxycholest-5-en-3.beta.-ol
SCHEMBL281941
7alpha-hydroxy cholesterol
5jk ,
7-a-hydroxycholesterol
AS-60936
(3beta,7alpha,9beta,14beta)-cholest-5-ene-3,7-diol
5-cholesten-3-beta,7-alpha-diol
7-alpha-hydroxy cholesterol
DTXSID40903965
CS-0111004
HY-N7264
Q155744
5-cholesten-3-beta, 7-alpha-diol
7 alpha -hydroxy cholesterol
(3beta,7alpha)-cholest-5-ene-3,7-diol
7alpha-hydroxycholest-5-en-3betaol
AKOS037645470
7(c) paragraph sign-hydroxycholesterol
7?-hydroxy cholesterol
A937396
PD046603

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In general, the oxysterols were more toxic to cancer cells and a set of compounds (9, 14, 21, 28, 45) with very high selectivity was identified."( Selective cytotoxicity of oxysterols through structural modulation on rings A and B. Synthesis, in vitro evaluation, and SAR.
Carvalho, JF; Moreira, JN; Sá E Melo, ML; Silva, MM; Simões, S, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role 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]

Drug Classes (3)

ClassDescription
7alpha-hydroxy steroidA 7-hydroxy steroid in which the hydroxy group at position 7 has an alpha-configuration.
oxysterolAn oxygenated derivative of cholesterol
3beta-hydroxy-Delta(5)-steroidAny 3beta-hydroxy-steroid that contains a double bond between positions 5 and 6.
[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 (20)

PathwayProteinsCompounds
Metabolism14961108
Metabolism of lipids500463
Metabolism of steroids111135
Bile acid and bile salt metabolism3171
Synthesis of bile acids and bile salts2068
Synthesis of bile acids and bile salts via 7alpha-hydroxycholesterol1644
Biological oxidations150276
Phase I - Functionalization of compounds69175
Cytochrome P450 - arranged by substrate type30110
Endogenous sterols1838
Steroids metabolism ( Steroids metabolism )1627
NADPH + Cholesterol + O2 = NADP+ + 7-Hydroxy-cholesterol + H2O ( Steroids metabolism )14
Cholesterol metabolism with Bloch and Kandutsch-Russell pathways039
Disorders of bile acid synthesis and biliary transport1840
Cholesterol metabolism214
Cholesterol biosynthesis pathway in hepatocytes1137
bile acid biosynthesis, neutral pathway644
Biochemical pathways: part I0466
Oxysterols derived from cholesterol3831
Sterols biosynthesis pathway015

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1055816Cytotoxicity against rat C6 cells assessed as cell viability after 24 hrs by trypan blue-based cell counting method2013European journal of medicinal chemistry, , Volume: 70Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system.
AID1055812Cytotoxicity against BALB/cJRj mouse astrocytes/oligodendrocytes assessed as cell viability at 50 uM after 24 hrs by trypan blue-based cell counting method2013European journal of medicinal chemistry, , Volume: 70Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system.
AID1055814Cytotoxicity against human SK-N-BE cells assessed as cell viability after 24 hrs by trypan blue-based cell counting method2013European journal of medicinal chemistry, , Volume: 70Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system.
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.
AID1055817Growth inhibition of mouse 158N cells after 24 hrs by trypan blue-based cell counting method2013European journal of medicinal chemistry, , Volume: 70Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system.
AID1055818Cytotoxicity against mouse 158N cells assessed as cell viability after 24 hrs by trypan blue-based cell counting method2013European journal of medicinal chemistry, , Volume: 70Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system.
AID1055811Growth inhibition of BALB/cJRj mouse astrocytes/oligodendrocytes at 50 uM after 24 hrs by trypan blue-based cell counting method2013European journal of medicinal chemistry, , Volume: 70Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system.
AID1055815Growth inhibition of rat C6 cells after 24 hrs by trypan blue-based cell counting method2013European journal of medicinal chemistry, , Volume: 70Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system.
AID1055813Growth inhibition of human SK-N-BE cells after 24 hrs by trypan blue-based cell counting method2013European journal of medicinal chemistry, , Volume: 70Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system.
AID617323Cytotoxicity against human HT-29 cells assessed as cell viability after 48 hrs by alamar blue assay2011Journal of medicinal chemistry, Sep-22, Volume: 54, Issue:18
Selective cytotoxicity of oxysterols through structural modulation on rings A and B. Synthesis, in vitro evaluation, and SAR.
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.
AID1346900Human GPR183 (Class A Orphans)2011Nature, Jul-27, Volume: 475, Issue:7357
Oxysterols direct B-cell migration through EBI2.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's4 (80.00)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: 12.84

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 Index12.84 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.63 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]