Page last updated: 2024-11-07

6-ketocholestanol

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

Description

6-ketocholestanol is a steroid compound that has been studied for its potential role in various biological processes, including cholesterol metabolism and inflammation. It is a derivative of cholesterol, with a ketone group at the 6-position. Its synthesis typically involves oxidation of cholesterol. Research has explored its potential effects on cell signaling pathways and its involvement in inflammatory responses. 6-ketocholestanol is of interest to researchers because of its unique structural features and its potential as a biomarker or therapeutic agent. Studies have investigated its impact on lipid metabolism, immune function, and its potential connection to certain diseases.'

6-ketocholestanol: RN given refers to the (3beta)-isomer; RN for cpd without isomeric designation not avail 5/90 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID102008
CHEMBL ID2418990
SCHEMBL ID4276094
MeSH IDM0176052
PubMed CID52931314
CHEBI ID166810
MeSH IDM0176052

Synonyms (37)

Synonym
nsc-178278
5.alpha.-cholestan-6-one, 3.beta.-hydroxy-
6-keto cholestanol
(3s,5s,8s,9s,10r,13r,14s,17r)-3-hydroxy-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
CHEMBL2418990
2v12d4a742 ,
nsc 178278
unii-2v12d4a742
einecs 214-640-5
5alpha-cholestan-6-one, 3beta-hydroxy-
cholestan-6-one, 3-hydroxy-, (3beta,5alpha)-
5alpha-cholestan-3beta-ol-6-one
3.beta.-hydroxy-5.alpha.-cholestan-6-one
cholestan-6-one, 3-hydroxy-, (3.beta.,5.alpha.)-
5.alpha.-cholestan-3.beta.-ol-6-one
(3s,5s,8s,9s,10r,13r,14s,17r)-17-[(1r)-1,5-dimethylhexyl]-3-hydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
SCHEMBL4276094
JQMQKOQOLPGBBE-ZNCJEFCDSA-N
3-hydroxycholestan-6-one, (3.beta.,5.alpha.)-
3beta-hydroxy-5alpha-cholestan-6-one
bdbm50045544
5alpha-cholestan-6-one
3b-hydroxy-5a-cholestan-6-one
NCGC00485025-01
5i+/--cholestan-3i(2)-ol-6-on
Q27255631
MS-26873
PD167312
HY-N9608
CS-0201561
AKOS040736217
6-oxocholestanol
CHEBI:166810
(3s,5s,10r,13r,17r)-3-hydroxy-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
6-ketocholestanol
5alpha-cholestan-6-oxo-3beta-ol
LMST01010276

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
"In this study, the effect of lipophilic counter-ions on the permeation of 5-aminolevulinic acid (ALA) in combination with skin impregnation by phloretin and 6-ketocholestanol was evaluated."( Influence of lipophilic counter-ions in combination with phloretin and 6-ketocholestanol on the skin permeation of 5-aminolevulinic acid.
Auner, BG; Hadgraft, J; Valenta, C, 2003
)
0.32

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
cholestanoidAny steroid based on a cholestane skeleton and its derivatives.
[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]

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 (12)

Assay IDTitleYearJournalArticle
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID780283Antitubercular activity against Mycobacterium tuberculosis H37Rv by MABA assay2013Bioorganic & medicinal chemistry letters, Nov-15, Volume: 23, Issue:22
Inhibitory effect of oxygenated cholestan-3β-ol derivatives on the growth of Mycobacterium tuberculosis.
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.
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.
AID780282Cytotoxicity against african green monkey Vero cells by tetrazolium dye reduction assay2013Bioorganic & medicinal chemistry letters, Nov-15, Volume: 23, Issue:22
Inhibitory effect of oxygenated cholestan-3β-ol derivatives on the growth of Mycobacterium tuberculosis.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID780281Selectivity index, ratio of IC50 for african green monkey Vero cells to MIC90 for Mycobacterium tuberculosis H37Rv2013Bioorganic & medicinal chemistry letters, Nov-15, Volume: 23, Issue:22
Inhibitory effect of oxygenated cholestan-3β-ol derivatives on the growth of Mycobacterium tuberculosis.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (57)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's20 (35.09)18.2507
2000's21 (36.84)29.6817
2010's12 (21.05)24.3611
2020's4 (7.02)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.61

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.61 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.61)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
Other51 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]