Page last updated: 2024-12-07

cholest-4-en-3-one

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

Description

cholest-4-en-3-one : A cholestanoid that is cholest-4-ene substituted by an oxo group at position 3. [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 CID91477
CHEMBL ID63243
CHEBI ID16175
SCHEMBL ID55896
MeSH IDM0040613

Synonyms (49)

Synonym
CHEBI:16175 ,
3-oxocholest-4-ene
einecs 210-005-1
nsc 63000
delta(sup 4)-cholestenone
nsc 134926
LMST01010015
cholestenone (delta 4)
cholest-4-en-3-one
C00599
cholestenone
4-cholestene-3-one
601-57-0
4-cholesten-3-one
(+)-4-cholesten-3-one, 98%
C-5800
(+)-3-oxo-4-cholestene
(+)-4-cholesten-3-one
CHEMBL63243
4-cholesten 3-one
3-keto-4-cholestene
BMSE000519
3-oxo-4-cholestene
k2b ,
(8alpha,9beta)-cholest-4-en-3-one
AKOS015955628
unii-7t94nhd99c
7t94nhd99c ,
bdbm92505
SCHEMBL55896
.delta.4-cholesten-3-one
.delta.-4-cholesten-3-one
mfcd00003663
.delta.4-cholestenone
(17.beta.)-17-octylandrost-4-en-3-one
DTXSID90872379
d4-cholestenone
(17b)-17-octylandrost-4-en-3-one
(8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-((r)-6-methylheptan-2-yl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one
Q27098418
(9s,10r,13r,14s,17r)-10,13-dimethyl-17-((r)-6-methylheptan-2-yl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one
(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,5h,7h,8h,9h,9ah,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-one
EN300-398595
HY-113365
CS-0062301
D94645
4-cholesten-3-on
AS-56879
Z2375482233
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (2)

ClassDescription
cholestanoidAny steroid based on a cholestane skeleton and its derivatives.
3-oxo-Delta(4) steroidA 3-oxo steroid conjugated to a C=C double bond at the alpha,beta position.
[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 (8)

PathwayProteinsCompounds
Cholesterol metabolism with Bloch and Kandutsch-Russell pathways039
Cholesterol biosynthesis pathway in hepatocytes1137
superpathway of cholesterol degradation II (cholesterol dehydrogenase)3058
superpathway of cholesterol degradation I (cholesterol oxidase)1755
cholesterol degradation to androstenedione I (cholesterol oxidase)1931
cholesterol degradation to androstenedione II (cholesterol dehydrogenase)1334
Biosynthesis and regulation of nematode bile acids05
Sterols biosynthesis pathway015

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Ghrelin O-acyltransferaseHomo sapiens (human)IC50 (µMol)1,000.00006.00007.50008.0000AID1802486
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 144Mycobacterium tuberculosis CDC1551Kd0.78000.36002.59905.3000AID1799791
Steroid C26-monooxygenaseMycobacterium tuberculosis CDC1551Kd0.78000.10002.59676.1000AID1799791
Steroid C26-monooxygenaseMycobacterium tuberculosis CDC1551Kd0.78000.36002.59905.3000AID1799791
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
peptide hormone processingGhrelin O-acyltransferaseHomo sapiens (human)
peptidyl-serine octanoylationGhrelin O-acyltransferaseHomo sapiens (human)
lipid modificationGhrelin O-acyltransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
O-acyltransferase activityGhrelin O-acyltransferaseHomo sapiens (human)
acyltransferase activity, transferring groups other than amino-acyl groupsGhrelin O-acyltransferaseHomo sapiens (human)
serine O-acyltransferase activityGhrelin O-acyltransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
endoplasmic reticulumGhrelin O-acyltransferaseHomo sapiens (human)
endoplasmic reticulum membraneGhrelin O-acyltransferaseHomo sapiens (human)
endoplasmic reticulum membraneGhrelin O-acyltransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID670265Activity of Mycobacterium tuberculosis CYP142A1 assessed as compound oxidation at 50 uM incubated for 1 hr at 25 degC by GC-MS method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
Substrate analog studies of the ω-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1.
AID540045Cytotoxicity against human LNCaP-FGC cells after 72 hrs by MTS assay2010Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23
Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.
AID1239268Protection against oxygen-glucose deprivation-induced cytotoxicity in Sprague-Dawley rat cerebral cortex primary neuronal cell cultures assessed as increase in cell viability at 0.1 to 250 uM added at onset of recovery period by MTT assay2015Journal of medicinal chemistry, Aug-27, Volume: 58, Issue:16
CholesteroNitrones for Stroke.
AID1239269Toxicity in Sprague-Dawley rat cerebral cortex primary neuronal cell cultures under oxygen-glucose deprivation conditions assessed as increase in cell viability at >50 uM added at onset of recovery period by MTT assay2015Journal of medicinal chemistry, Aug-27, Volume: 58, Issue:16
CholesteroNitrones for Stroke.
AID670264Activity of Mycobacterium tuberculosis CYP125A1 assessed as compound oxidation at 50 uM incubated for 1 hr at 25 degC by GC-MS method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
Substrate analog studies of the ω-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1.
AID226241Feed efficiency was calculated by dividing body weight gain by feed consumption in mouse1998Bioorganic & medicinal chemistry letters, Aug-18, Volume: 8, Issue:16
The cholesterol metabolite cholest-4-en-3-one and its 3-oxo derivatives suppress body weight gain, body fat accumulation and serum lipid concentration in mice.
AID671402Activity of Mycobacterium tuberculosis CYP124A1 assessed as compound oxidation at 50 uM incubated for 1 hr at 25 degC by GC-MS method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
Substrate analog studies of the ω-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1.
AID540042Cytotoxicity against human DU4475 cells after 72 hrs by MTS assay2010Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23
Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.
AID671391Binding affinity to Mycobacterium tuberculosis CYP124A1 assessed as type 1 binding mode at 0.05 to 0.2 uM by UV-visible spectrophotometry2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
Substrate analog studies of the ω-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1.
AID108709Compound was evaluated for its potency in CDF1 mice and the abdominal fat weight was determined1998Bioorganic & medicinal chemistry letters, Aug-18, Volume: 8, Issue:16
The cholesterol metabolite cholest-4-en-3-one and its 3-oxo derivatives suppress body weight gain, body fat accumulation and serum lipid concentration in mice.
AID7635Compound was evaluated for its potency in CDF1 mice and the serum metabolite levels were determined1998Bioorganic & medicinal chemistry letters, Aug-18, Volume: 8, Issue:16
The cholesterol metabolite cholest-4-en-3-one and its 3-oxo derivatives suppress body weight gain, body fat accumulation and serum lipid concentration in mice.
AID671392Binding affinity to Mycobacterium tuberculosis CYP125A1 assessed as type 1 binding mode at 0.05 to 0.2 uM by UV-visible spectrophotometry2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
Substrate analog studies of the ω-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1.
AID671393Binding affinity to Mycobacterium tuberculosis CYP142A1 assessed as type 1 binding mode at 0.05 to 0.2 uM by UV-visible spectrophotometry2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
Substrate analog studies of the ω-regiospecificity of Mycobacterium tuberculosis cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1.
AID540048Cytotoxicity against human DU145 cells after 72 hrs by MTS assay2010Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23
Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.
AID110288Evaluated for potency in CDF1 mice and the inhibition of body weight gain was determined1998Bioorganic & medicinal chemistry letters, Aug-18, Volume: 8, Issue:16
The cholesterol metabolite cholest-4-en-3-one and its 3-oxo derivatives suppress body weight gain, body fat accumulation and serum lipid concentration in mice.
AID540043Cytotoxicity against human MDA-MB-468 cells after 72 hrs by MTS assay2010Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23
Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.
AID540044Cytotoxicity against human PC3 cells after 72 hrs by MTS assay2010Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23
Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.
AID7636Compound was evaluated for its potency in CDF1 mice and the serum triglyceride levels were determined1998Bioorganic & medicinal chemistry letters, Aug-18, Volume: 8, Issue:16
The cholesterol metabolite cholest-4-en-3-one and its 3-oxo derivatives suppress body weight gain, body fat accumulation and serum lipid concentration in mice.
AID113559Evaluated for potency in CDF1 mice and the ability of it to decrease feed consumption was determined1998Bioorganic & medicinal chemistry letters, Aug-18, Volume: 8, Issue:16
The cholesterol metabolite cholest-4-en-3-one and its 3-oxo derivatives suppress body weight gain, body fat accumulation and serum lipid concentration in mice.
AID7634Compound was evaluated for its potency in CDF1 mice and the serum cholesterol levels were determined1998Bioorganic & medicinal chemistry letters, Aug-18, Volume: 8, Issue:16
The cholesterol metabolite cholest-4-en-3-one and its 3-oxo derivatives suppress body weight gain, body fat accumulation and serum lipid concentration in mice.
AID540046Cytotoxicity against human HCT116 cells after 72 hrs by MTS assay2010Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23
Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.
AID540047Cytotoxicity against human MDA-MB-231 cells after 72 hrs by MTS assay2010Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23
Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.
AID1802486GOAT Activity Assay from Article 10.1021/acs.biochem.6b01008: \\Synthetic Triterpenoid Inhibition of Human Ghrelin O-Acyltransferase: The Involvement of a Functionally Required Cysteine Provides Mechanistic Insight into Ghrelin Acylation.\\2017Biochemistry, 02-21, Volume: 56, Issue:7
Synthetic Triterpenoid Inhibition of Human Ghrelin O-Acyltransferase: The Involvement of a Functionally Required Cysteine Provides Mechanistic Insight into Ghrelin Acylation.
AID1799791Binding Assay from Article 10.1074/jbc.M110.164293: \\Structural and biochemical characterization of Mycobacterium tuberculosis CYP142: evidence for multiple cholesterol 27-hydroxylase activities in a human pathogen.\\2010The Journal of biological chemistry, Dec-03, Volume: 285, Issue:49
Structural and biochemical characterization of Mycobacterium tuberculosis CYP142: evidence for multiple cholesterol 27-hydroxylase activities in a human pathogen.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (68)

TimeframeStudies, This Drug (%)All Drugs %
pre-199016 (23.53)18.7374
1990's14 (20.59)18.2507
2000's12 (17.65)29.6817
2010's25 (36.76)24.3611
2020's1 (1.47)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.96

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 Index29.96 (24.57)
Research Supply Index4.26 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index35.70 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.96)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.45%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other68 (98.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]