Page last updated: 2024-11-08

cholest-5-en-3 beta,7 alpha-diol, (3beta,7beta)-isomer

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

Cross-References

ID SourceID
PubMed CID473141
CHEMBL ID497834
CHEBI ID42989
SCHEMBL ID532559
MeSH IDM0311569

Synonyms (39)

Synonym
(3.beta.,7.beta.)-7-hydroxycholest-5-en-3-ol
(3s,7r,8s,9s,10r,13r,14s,17r)-17-[(1r)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-3,7-diol
7.beta.-hydroxycholesterol
(3beta,7beta)-cholest-5-ene-3,7-diol
cholest-5-ene-3beta,7beta-diol
CHEBI:42989 ,
566-27-8
DB04706
LMST01010047
7beta-hydroxycholesterol
5-cholestene-3beta,7beta-diol
(3s,7r,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
CHEMBL497834 ,
cholest-5-ene-3,7-diol, (3beta,7beta)-
n9616291j4 ,
unii-n9616291j4
7-hydroxycholesterol, (7beta)-
7beta-hydroxy cholesterol
7-beta-ohc
gtpl4352
SCHEMBL532559
7.beta.-hydroxycholest-5-en-3.beta.-ol
cholest-5-ene-3,7-diol, (3.beta.,7.beta.)-
7-hydroxycholesterol, (7.beta.)-
.delta.5-cholestene-3.beta.,7.beta.-diol
bdbm50045545
AKOS027381831
(3s,7r,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-((r)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,7-diol
(3beta,7alpha,14beta,17alpha)-cholest-5-ene-3,7-diol
'(3beta,7beta)-cholest-5-ene-3,7-diol'
(7beta)-hydroxycholesterol
Q27074031
5-cholesten-3beta,7beta-diol
DTXSID60862207
7b-hydroxycholesterol
CS-0061837
HY-113341
PD005886
cholest-5-ene-3,7-diol, (3.beta.,7.beta.,8.epsilon.)-

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]

Drug Classes (2)

ClassDescription
7beta-hydroxy steroidA 7-hydroxy steroid in which the hydroxy group at position 7 has beta-configuration.
oxysterolAn oxygenated derivative of cholesterol
[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

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NPC1-like intracellular cholesterol transporter 1Homo sapiens (human)EC50 (µMol)3.40001.70003.52508.7000AID1179742
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
cholesterol biosynthetic processNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
intestinal cholesterol absorptionNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
cholesterol transportNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
lipoprotein metabolic processNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
vitamin E metabolic processNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
vitamin transportNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
cellular response to sterol depletionNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
cholesterol homeostasisNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
protein bindingNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
vitamin E bindingNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
cholesterol bindingNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
small GTPase bindingNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
myosin V bindingNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
protein homodimerization activityNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
plasma membraneNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
apical plasma membraneNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
cytoplasmic vesicle membraneNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
plasma membraneNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID695019Selectivity ratio of agonist activity at Hh receptor over agonist activity at LXR in mouse C3H10T1/2 cells2012ACS medicinal chemistry letters, Oct-11, Volume: 3, Issue:10
Structure-activity relationships for side chain oxysterol agonists of the hedgehog signaling pathway.
AID617330Cytotoxicity against human ARPE19 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.
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.
AID695017Agonist activity at Hh receptor in mouse C3H10T1/2 cells assessed as fold increase in Gli1 expression at 5 uM by RT-PCR analysis relative to control2012ACS medicinal chemistry letters, Oct-11, Volume: 3, Issue:10
Structure-activity relationships for side chain oxysterol agonists of the hedgehog signaling pathway.
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.
AID537057Cytotoxicity against human MCF7 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.
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.
AID537059Cytotoxicity against human BJ 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.
AID537058Cytotoxicity against HMEC1 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.
AID537056Cytotoxicity against human HepG2 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.
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.
AID537064Chemical stability of the compound in 0.1 M aqueous acetate buffer assessed as hydrolysis at pH 4.6 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.
AID537053Cytotoxicity against human A549 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.
AID617326Cytotoxicity against human SH-SY5Y 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.
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.
AID768322Binding affinity to human GFP-tagged NPC1L1 L1072T/L1168I mutant expressed in HEK293 cells assessed as localization to endoplasmic reticulum and plasma membrane after 24 hrs by fluorescence microscopic analysis2013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Structure-activity relationship studies of Niemann-Pick type C1-like 1 (NPC1L1) ligands identified by screening assay monitoring pharmacological chaperone effect.
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.
AID375538Cytotoxicity against human BJ 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.
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.
AID537060Selectivity index, ratio of IC50 for human ARPE19 cells to IC50 for human LAMA-84 cells2010Journal 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.
AID537055Cytotoxicity against human ARPE19 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.
AID617331Cytotoxicity against human BJ 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.
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.
AID617324Cytotoxicity against human LAMA-84 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.
AID375537Cytotoxicity against human LAMA-84 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.
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.
AID1179742Binding affinity to FLAG/tGFP-tagged NPC1 I1061T mutant (unknown origin) expressed in HEK293 cells assessed as localization after 24 hrs by fluorescence microscopy2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
Structure-activity relationships of oxysterol-derived pharmacological chaperones for Niemann-Pick type C1 protein.
AID617328Cytotoxicity against human A549 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.
AID695018Agonist activity at LXR in mouse C3H10T1/2 cells assessed as fold increase in ABCA1 expression at 5 uM by RT-PCR analysis relative to control2012ACS medicinal chemistry letters, Oct-11, Volume: 3, Issue:10
Structure-activity relationships for side chain oxysterol agonists of the hedgehog signaling pathway.
AID537063Chemical stability of the compound in 0.1 M aqueous citrate buffer assessed as hydrolysis at pH 3 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.
AID617325Cytotoxicity against human MCF7 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.
AID617334Selectivity index, ratio of IC50 for human ARPE19 cells to IC50 for human HT-29 cells2011Journal 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.
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.
AID537052Cytotoxicity against human LAMA-84 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.
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.
AID617329Cytotoxicity against human PC3 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.
AID617327Cytotoxicity against human HepG2 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.
AID537054Cytotoxicity against human PC3 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.
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 (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (12.50)29.6817
2010's7 (87.50)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: 12.72

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 Index12.72 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]