Page last updated: 2024-11-13

cholenic acid dimethylamide

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Description

cholenic acid dimethylamide: binds LXRalpha receptor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID24768125
CHEMBL ID352837
SCHEMBL ID13366259
MeSH IDM0385353

Synonyms (13)

Synonym
cholenic acid dimethylamide
(4r)-4-[(1s,2r,5s,10s,11s,14r,15r)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-7-en-14-yl]-n,n-dimethylpentanamide
bdbm20186
CHEMBL352837
SCHEMBL13366259
dmhca
MS-26842
(3.beta.)-3-hydroxy-n,n-dimethyl-chol-5-en-24-amide
HY-129098
CS-0103576
(4r)-4-[(3s,8s,9s,10r,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]-n,n-dimethylpentanamide
(3beta)-3-hydroxy-n,n-dimethyl-chol-5-en-24-amide
AKOS040758351
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Delta(24)-sterol reductaseHomo sapiens (human)IC50 (µMol)0.00070.00070.00070.0007AID1502695
[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)
Oxysterols receptor LXR-alphaHomo sapiens (human)EC50 (µMol)0.25400.00010.63026.7100AID101835; AID1414113; AID1797959
Oxysterols receptor LXR-betaRattus norvegicus (Norway rat)EC50 (µMol)0.12400.03000.07700.1240AID1542682
NPC1-like intracellular cholesterol transporter 1Homo sapiens (human)EC50 (µMol)3.10001.70003.52508.7000AID1179742
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Delta(24)-sterol reductaseHomo sapiens (human)INH1.00001.00001.00001.0000AID1502693
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (57)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IIOxysterols receptor LXR-alphaHomo sapiens (human)
hormone-mediated signaling pathwayOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of macrophage derived foam cell differentiationOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of triglyceride biosynthetic processOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of cholesterol effluxOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of cholesterol storageOxysterols receptor LXR-alphaHomo sapiens (human)
intracellular receptor signaling pathwayOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of lipid transportOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of cholesterol transportOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of transporter activityOxysterols receptor LXR-alphaHomo sapiens (human)
response to progesteroneOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of toll-like receptor 4 signaling pathwayOxysterols receptor LXR-alphaHomo sapiens (human)
phosphatidylcholine acyl-chain remodelingOxysterols receptor LXR-alphaHomo sapiens (human)
cholesterol homeostasisOxysterols receptor LXR-alphaHomo sapiens (human)
regulation of circadian rhythmOxysterols receptor LXR-alphaHomo sapiens (human)
mRNA transcription by RNA polymerase IIOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of macrophage activationOxysterols receptor LXR-alphaHomo sapiens (human)
apoptotic cell clearanceOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of fatty acid biosynthetic processOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of proteolysisOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of DNA-templated transcriptionOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of lipid biosynthetic processOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of pinocytosisOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of inflammatory responseOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of lipoprotein lipase activityOxysterols receptor LXR-alphaHomo sapiens (human)
positive regulation of protein metabolic processOxysterols receptor LXR-alphaHomo sapiens (human)
lipid homeostasisOxysterols receptor LXR-alphaHomo sapiens (human)
sterol homeostasisOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of type II interferon-mediated signaling pathwayOxysterols receptor LXR-alphaHomo sapiens (human)
triglyceride homeostasisOxysterols receptor LXR-alphaHomo sapiens (human)
cellular response to lipopolysaccharideOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of pancreatic juice secretionOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of secretion of lysosomal enzymesOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of cold-induced thermogenesisOxysterols receptor LXR-alphaHomo sapiens (human)
negative regulation of response to endoplasmic reticulum stressOxysterols receptor LXR-alphaHomo sapiens (human)
cell differentiationOxysterols receptor LXR-alphaHomo sapiens (human)
cholesterol biosynthetic processDelta(24)-sterol reductaseHomo sapiens (human)
cholesterol biosynthetic processDelta(24)-sterol reductaseHomo sapiens (human)
Ras protein signal transductionDelta(24)-sterol reductaseHomo sapiens (human)
protein localizationDelta(24)-sterol reductaseHomo sapiens (human)
negative regulation of cell population proliferationDelta(24)-sterol reductaseHomo sapiens (human)
response to hormoneDelta(24)-sterol reductaseHomo sapiens (human)
tissue developmentDelta(24)-sterol reductaseHomo sapiens (human)
male genitalia developmentDelta(24)-sterol reductaseHomo sapiens (human)
plasminogen activationDelta(24)-sterol reductaseHomo sapiens (human)
cholesterol biosynthetic process via desmosterolDelta(24)-sterol reductaseHomo sapiens (human)
cholesterol biosynthetic process via lathosterolDelta(24)-sterol reductaseHomo sapiens (human)
amyloid precursor protein catabolic processDelta(24)-sterol reductaseHomo sapiens (human)
skin developmentDelta(24)-sterol reductaseHomo sapiens (human)
membrane organizationDelta(24)-sterol reductaseHomo sapiens (human)
steroid metabolic processDelta(24)-sterol reductaseHomo sapiens (human)
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 (21)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingOxysterols receptor LXR-alphaHomo sapiens (human)
transcription cis-regulatory region bindingOxysterols receptor LXR-alphaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificOxysterols receptor LXR-alphaHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificOxysterols receptor LXR-alphaHomo sapiens (human)
DNA bindingOxysterols receptor LXR-alphaHomo sapiens (human)
nuclear receptor activityOxysterols receptor LXR-alphaHomo sapiens (human)
protein bindingOxysterols receptor LXR-alphaHomo sapiens (human)
zinc ion bindingOxysterols receptor LXR-alphaHomo sapiens (human)
cholesterol bindingOxysterols receptor LXR-alphaHomo sapiens (human)
chromatin DNA bindingOxysterols receptor LXR-alphaHomo sapiens (human)
sterol response element bindingOxysterols receptor LXR-alphaHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingOxysterols receptor LXR-alphaHomo sapiens (human)
delta24(24-1) sterol reductase activityDelta(24)-sterol reductaseHomo sapiens (human)
protein bindingDelta(24)-sterol reductaseHomo sapiens (human)
oxidoreductase activity, acting on the CH-CH group of donors, NAD or NADP as acceptorDelta(24)-sterol reductaseHomo sapiens (human)
enzyme bindingDelta(24)-sterol reductaseHomo sapiens (human)
peptide antigen bindingDelta(24)-sterol reductaseHomo sapiens (human)
delta24-sterol reductase activityDelta(24)-sterol reductaseHomo sapiens (human)
FAD bindingDelta(24)-sterol reductaseHomo sapiens (human)
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 (14)

Processvia Protein(s)Taxonomy
nucleusOxysterols receptor LXR-alphaHomo sapiens (human)
nucleoplasmOxysterols receptor LXR-alphaHomo sapiens (human)
cytoplasmOxysterols receptor LXR-alphaHomo sapiens (human)
cytosolOxysterols receptor LXR-alphaHomo sapiens (human)
RNA polymerase II transcription regulator complexOxysterols receptor LXR-alphaHomo sapiens (human)
chromatinOxysterols receptor LXR-alphaHomo sapiens (human)
receptor complexOxysterols receptor LXR-alphaHomo sapiens (human)
nucleusOxysterols receptor LXR-alphaHomo sapiens (human)
Golgi membraneDelta(24)-sterol reductaseHomo sapiens (human)
nucleusDelta(24)-sterol reductaseHomo sapiens (human)
endoplasmic reticulumDelta(24)-sterol reductaseHomo sapiens (human)
endoplasmic reticulum membraneDelta(24)-sterol reductaseHomo sapiens (human)
membraneDelta(24)-sterol reductaseHomo sapiens (human)
cytoplasmDelta(24)-sterol reductaseHomo sapiens (human)
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 (20)

Assay IDTitleYearJournalArticle
AID1389142Antagonist activity at human full length LXRbeta expressed in human BHK21 cells co-expressing human pSG5/RXRalpha assessed as inhibition of GW3965-induced receptor activation at 10 uM after 18 hrs by luciferase reporter gene assay2018Bioorganic & medicinal chemistry, 03-01, Volume: 26, Issue:5
Synthesis and activity evaluation of a series of cholanamides as modulators of the liver X receptors.
AID1502693Inhibition of DHCR24 in human HL60 cells assessed as compound level causing induction of sterol accumulation incubated for 24 hrs by GC-MS analysis2017European journal of medicinal chemistry, Nov-10, Volume: 140New chemotype of selective and potent inhibitors of human delta 24-dehydrocholesterol reductase.
AID1389140Antagonist activity at human full length LXRalpha expressed in human BHK21 cells co-expressing human pSG5/RXRalpha assessed as inhibition of GW3965-induced receptor activation at 10 uM after 18 hrs by luciferase reporter gene assay2018Bioorganic & medicinal chemistry, 03-01, Volume: 26, Issue:5
Synthesis and activity evaluation of a series of cholanamides as modulators of the liver X receptors.
AID1502695Inhibition of DHCR24-mediated cholesterol biosynthesis in human HL60 cells assessed as inhibition of 2-[13C]acetate incorporation into newly synthesized cholesterol after 24 hrs GC/MS analysis2017European journal of medicinal chemistry, Nov-10, Volume: 140New chemotype of selective and potent inhibitors of human delta 24-dehydrocholesterol reductase.
AID1542682Transactivation of rat LXRbeta expressed in HEK293FT cells measured after 14 to 18 hrs by dual-luciferase reporter gene assay2019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Structural requirements of cholenamide derivatives as the LXR ligands.
AID1389139Agonist activity at human full length LXRalpha expressed in human BHK21 cells co-expressing human pSG5/RXRalpha at 10 uM after 18 hrs by luciferase reporter gene assay relative to GW39652018Bioorganic & medicinal chemistry, 03-01, Volume: 26, Issue:5
Synthesis and activity evaluation of a series of cholanamides as modulators of the liver X receptors.
AID1414114Agonist activity at human LXRalpha expressed in HEK293 cells after 24 hrs by One-Glo luciferase reporter gene assay relative to TO9013172018Journal of medicinal chemistry, 12-27, Volume: 61, Issue:24
Recent Advances in the Medicinal Chemistry of Liver X Receptors.
AID101835Concentration required for half maximal activity was calculated in human nuclear oxysterol receptor liver X receptor-alpha in LiSA.2001Journal of medicinal chemistry, Mar-15, Volume: 44, Issue:6
Pharmacophore analysis of the nuclear oxysterol receptor LXRalpha.
AID1502681Cytotoxicity in human HL60 cells by MTT assay2017European journal of medicinal chemistry, Nov-10, Volume: 140New chemotype of selective and potent inhibitors of human delta 24-dehydrocholesterol reductase.
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.
AID1414113Agonist activity at human LXRalpha expressed in HEK293 cells after 24 hrs by One-Glo luciferase reporter gene assay2018Journal of medicinal chemistry, 12-27, Volume: 61, Issue:24
Recent Advances in the Medicinal Chemistry of Liver X Receptors.
AID101844Tested for its ability to activate Liver X receptor-alpha expressed as Relative efficacy determined by maximal increase in relative fluorescence in LiSA2001Journal of medicinal chemistry, Mar-15, Volume: 44, Issue:6
Pharmacophore analysis of the nuclear oxysterol receptor LXRalpha.
AID1542683Transactivation of rat LXRbeta expressed in HEK293FT cells measured after 14 to 18 hrs by dual-luciferase reporter gene assay relative to T09013172019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Structural requirements of cholenamide derivatives as the LXR ligands.
AID1542678Transactivation of rat LXRbeta expressed in HEK293FT cells at 5 uM measured after 14 to 18 hrs by dual-luciferase reporter gene assay2019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Structural requirements of cholenamide derivatives as the LXR ligands.
AID1502687Induction of sterol accumulation in human HL60 cells assessed as desmosterol accumulation at 50 uM incubated for 24 hrs by GC-MS analysis2017European journal of medicinal chemistry, Nov-10, Volume: 140New chemotype of selective and potent inhibitors of human delta 24-dehydrocholesterol reductase.
AID1502682Induction of sterol accumulation in human HL60 cells assessed as desmosterol accumulation at 1 uM incubated for 24 hrs by GC-MS analysis2017European journal of medicinal chemistry, Nov-10, Volume: 140New chemotype of selective and potent inhibitors of human delta 24-dehydrocholesterol reductase.
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.
AID1542677Transactivation of rat LXRalpha expressed in HEK293FT cells at 5 uM measured after 14 to 18 hrs by dual-luciferase reporter gene assay2019Bioorganic & medicinal chemistry letters, 06-01, Volume: 29, Issue:11
Structural requirements of cholenamide derivatives as the LXR ligands.
AID1389141Agonist activity at human full length LXRbeta expressed in human BHK21 cells co-expressing human pSG5/RXRalpha at 10 uM after 18 hrs by luciferase reporter gene assay relative to GW39652018Bioorganic & medicinal chemistry, 03-01, Volume: 26, Issue:5
Synthesis and activity evaluation of a series of cholanamides as modulators of the liver X receptors.
AID1797959Cell-Free Ligand Sensing Assay (LiSA)-LXRalpha-SRC1 Assay from Article 10.1021/jm0004749: \\Pharmacophore analysis of the nuclear oxysterol receptor LXRalpha.\\2001Journal of medicinal chemistry, Mar-15, Volume: 44, Issue:6
Pharmacophore analysis of the nuclear oxysterol receptor LXRalpha.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (14.29)29.6817
2010's6 (85.71)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: 13.25

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 Index13.25 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index5.33 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.25)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]