Page last updated: 2024-12-08

24-norursodeoxycholic acid

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

Description

24-norursodeoxycholic acid: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID192254
CHEMBL ID1254990
SCHEMBL ID18472036
MeSH IDM0216966

Synonyms (29)

Synonym
bdbm50334958
(r)-3-((3r,5s,7s,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)butanoic acid
24-norursodeoxycholic acid
99697-24-2
24-nor ursodeoxycholic acid
(3r)-3-[(3r,5s,7s,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]butanoic acid
nor-ursodeoxycholic acid
norursodeoxycholic acid
norucholic acid
CHEMBL1254990 ,
8a5g600d9v ,
unii-8a5g600d9v
nor-udca
24-norcholan-23-oic acid, 3,7-dihydroxy-, (3alpha,5beta,7beta)-
3.alpha.,7.beta.-dihydroxy-24-nor-5.beta.-cholan-23-oic acid
norucholic acid [who-dd]
24-norcholan-23-oic acid, 3,7-dihydroxy-, (3.alpha.,5.beta.,7.beta.)-
(3.alpha.,5.beta.,7.beta.)-3,7-dihydroxy-24-norcholan-23-oic acid
norucholic acid [inn]
24-nor-3alpha,7beta-dihydroxy-5beta-cholan-23-oic acid
LMST04060021
SCHEMBL18472036
HY-101737
CS-6534
EX-A4681
Q27270089
MS-26185
nor-udcanor-udca
AKOS040732271

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Finally, CDCA, DCA and LagoDCA were prominent outliers being more toxic than predicted by RMw."( Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
Gilmer, JF; Keaveney, R; Kelleher, D; Long, A; Majer, F; Peta, VK; Sharma, R; Wang, J, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glucocorticoid receptorHomo sapiens (human)EC50 (µMol)105.30000.00040.05401.0000AID554023
G-protein coupled bile acid receptor 1Homo sapiens (human)EC50 (µMol)47.20000.02372.52598.9000AID324923
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (37)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
regulation of gluconeogenesisGlucocorticoid receptorHomo sapiens (human)
chromatin organizationGlucocorticoid receptorHomo sapiens (human)
regulation of DNA-templated transcriptionGlucocorticoid receptorHomo sapiens (human)
apoptotic processGlucocorticoid receptorHomo sapiens (human)
chromosome segregationGlucocorticoid receptorHomo sapiens (human)
signal transductionGlucocorticoid receptorHomo sapiens (human)
glucocorticoid metabolic processGlucocorticoid receptorHomo sapiens (human)
gene expressionGlucocorticoid receptorHomo sapiens (human)
microglia differentiationGlucocorticoid receptorHomo sapiens (human)
adrenal gland developmentGlucocorticoid receptorHomo sapiens (human)
regulation of glucocorticoid biosynthetic processGlucocorticoid receptorHomo sapiens (human)
synaptic transmission, glutamatergicGlucocorticoid receptorHomo sapiens (human)
maternal behaviorGlucocorticoid receptorHomo sapiens (human)
intracellular glucocorticoid receptor signaling pathwayGlucocorticoid receptorHomo sapiens (human)
glucocorticoid mediated signaling pathwayGlucocorticoid receptorHomo sapiens (human)
positive regulation of neuron apoptotic processGlucocorticoid receptorHomo sapiens (human)
negative regulation of DNA-templated transcriptionGlucocorticoid receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
astrocyte differentiationGlucocorticoid receptorHomo sapiens (human)
cell divisionGlucocorticoid receptorHomo sapiens (human)
mammary gland duct morphogenesisGlucocorticoid receptorHomo sapiens (human)
motor behaviorGlucocorticoid receptorHomo sapiens (human)
cellular response to steroid hormone stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to glucocorticoid stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to dexamethasone stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to transforming growth factor beta stimulusGlucocorticoid receptorHomo sapiens (human)
neuroinflammatory responseGlucocorticoid receptorHomo sapiens (human)
positive regulation of miRNA transcriptionGlucocorticoid receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayGlucocorticoid receptorHomo sapiens (human)
regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
cell surface bile acid receptor signaling pathwayG-protein coupled bile acid receptor 1Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeG-protein coupled bile acid receptor 1Homo sapiens (human)
cellular response to bile acidG-protein coupled bile acid receptor 1Homo sapiens (human)
positive regulation of cholangiocyte proliferationG-protein coupled bile acid receptor 1Homo sapiens (human)
regulation of bicellular tight junction assemblyG-protein coupled bile acid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathwayG-protein coupled bile acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (22)

Processvia Protein(s)Taxonomy
RNA polymerase II transcription regulatory region sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
core promoter sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription factor activityGlucocorticoid receptorHomo sapiens (human)
RNA bindingGlucocorticoid receptorHomo sapiens (human)
nuclear receptor activityGlucocorticoid receptorHomo sapiens (human)
nuclear glucocorticoid receptor activityGlucocorticoid receptorHomo sapiens (human)
steroid bindingGlucocorticoid receptorHomo sapiens (human)
protein bindingGlucocorticoid receptorHomo sapiens (human)
zinc ion bindingGlucocorticoid receptorHomo sapiens (human)
TBP-class protein bindingGlucocorticoid receptorHomo sapiens (human)
protein kinase bindingGlucocorticoid receptorHomo sapiens (human)
identical protein bindingGlucocorticoid receptorHomo sapiens (human)
Hsp90 protein bindingGlucocorticoid receptorHomo sapiens (human)
steroid hormone bindingGlucocorticoid receptorHomo sapiens (human)
sequence-specific double-stranded DNA bindingGlucocorticoid receptorHomo sapiens (human)
estrogen response element bindingGlucocorticoid receptorHomo sapiens (human)
protein bindingG-protein coupled bile acid receptor 1Homo sapiens (human)
bile acid receptor activityG-protein coupled bile acid receptor 1Homo sapiens (human)
G protein-coupled bile acid receptor activityG-protein coupled bile acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
nucleusGlucocorticoid receptorHomo sapiens (human)
nucleusGlucocorticoid receptorHomo sapiens (human)
nucleoplasmGlucocorticoid receptorHomo sapiens (human)
cytoplasmGlucocorticoid receptorHomo sapiens (human)
mitochondrial matrixGlucocorticoid receptorHomo sapiens (human)
centrosomeGlucocorticoid receptorHomo sapiens (human)
spindleGlucocorticoid receptorHomo sapiens (human)
cytosolGlucocorticoid receptorHomo sapiens (human)
membraneGlucocorticoid receptorHomo sapiens (human)
nuclear speckGlucocorticoid receptorHomo sapiens (human)
synapseGlucocorticoid receptorHomo sapiens (human)
chromatinGlucocorticoid receptorHomo sapiens (human)
protein-containing complexGlucocorticoid receptorHomo sapiens (human)
cytoplasmG-protein coupled bile acid receptor 1Homo sapiens (human)
plasma membraneG-protein coupled bile acid receptor 1Homo sapiens (human)
receptor complexG-protein coupled bile acid receptor 1Homo sapiens (human)
plasma membraneG-protein coupled bile acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1161667Agonist activity at human GPBAR1 expressed in HEK293T cells assessed as stimulation of cAMP response element-mediated receptor transactivation at 10 uM by luciferase reporter gene assay2014Journal of medicinal chemistry, Sep-25, Volume: 57, Issue:18
Modification on ursodeoxycholic acid (UDCA) scaffold. discovery of bile acid derivatives as selective agonists of cell-surface G-protein coupled bile acid receptor 1 (GP-BAR1).
AID1161670Antagonist activity against FXR (unknown origin) expressed in human HepG2 cells assessed as inhibition of CDCA-induced stimulation of FXR response element IR1-mediated receptor transactivation at 50 uM by luciferase reporter gene assay2014Journal of medicinal chemistry, Sep-25, Volume: 57, Issue:18
Modification on ursodeoxycholic acid (UDCA) scaffold. discovery of bile acid derivatives as selective agonists of cell-surface G-protein coupled bile acid receptor 1 (GP-BAR1).
AID554024Modulation of glucocorticoid receptor in human SKGT4 cells assessed as receptor translocation from cytoplasm to nucleus at 300 uM after 4 hrs by Hoechst staining relative to Dexamethasone2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Ursodeoxycholic acid amides as novel glucocorticoid receptor modulators.
AID515399Cytotoxicity against human HuH7 cells assessed as cell viability at 500 uM after 24 hrs by MTT assay relative to control2010Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18
Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
AID515398Cytotoxicity against human HET-1A cells assessed as cell viability after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18
Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
AID554023Modulation of glucocorticoid receptor in human SKGT4 cells assessed as receptor translocation from cytoplasm to nucleus after 4 hrs by Hoechst staining relative to Dexamethasone2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Ursodeoxycholic acid amides as novel glucocorticoid receptor modulators.
AID324924Agonist activity at human TGR5 expressed in CHO cells by luciferase assay relative to lithocholic acid2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.
AID324923Agonist activity at human TGR5 expressed in CHO cells by luciferase assay2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.
AID1161665Agonist activity at FXR (unknown origin) expressed in human HepG2 cells assessed as stimulation of FXR response element IR1-mediated receptor transactivation at 10 uM by luciferase reporter gene assay2014Journal of medicinal chemistry, Sep-25, Volume: 57, Issue:18
Modification on ursodeoxycholic acid (UDCA) scaffold. discovery of bile acid derivatives as selective agonists of cell-surface G-protein coupled bile acid receptor 1 (GP-BAR1).
AID515400Cytotoxicity against human HET-1A cells assessed as cell viability at 500 uM after 24 hrs by MTT assay relative to control2010Bioorganic & medicinal chemistry, Sep-15, Volume: 18, Issue:18
Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (35)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (2.86)18.2507
2000's5 (14.29)29.6817
2010's26 (74.29)24.3611
2020's3 (8.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.36

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 Index32.36 (24.57)
Research Supply Index3.64 (2.92)
Research Growth Index5.50 (4.65)
Search Engine Demand Index36.99 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.36)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (5.71%)5.53%
Reviews10 (28.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (65.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]