Page last updated: 2024-12-08

sulfolithocholic acid

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

Description

sulfolithocholic acid: RN refers to (3alpha,5beta)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

lithocholic acid sulfate : A steroid sulfate that is lithocholic acid in which the hydroxy hydrogen at position 3 has been replaced by a sulfo group. [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 CID451489
CHEMBL ID260315
CHEBI ID35421
SCHEMBL ID232940
MeSH IDM0062550

Synonyms (29)

Synonym
(3alpha,5beta)-3-(sulfooxy)cholan-24-oic acid
sulfolithocholic acid
3alpha-sulfooxy-5beta-cholan-24-oic acid
lithocholic acid sulfate
lithocholic acid 3-sulfate
CHEBI:35421 ,
34669-57-3
cholan-24-oic acid, 3-(sulfooxy)-, (3a-alpha,5-beta)-
lithocholic acid, 3-sulfate
(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3-sulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoic acid
3-hydroxy-cholan-24-oic acid, 3-sulfate (3-.alpha., 5-.beta.)
CHEMBL260315 ,
LMST05020015
unii-0enk5nmi1i
0enk5nmi1i ,
bdbm50375583
SCHEMBL232940
lithocholic acid 3.alpha.-sulfate
(4r)-4-((3r,5r,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3-sulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta(a)phenanthren-17-yl)pentanoic acid
cholan-24-oic acid, 3-(sulfooxy)-, (3.alpha.,5.beta.)-
(3.alpha.,5.beta.)-3-(sulfooxy)cholan-24-oic acid
3.alpha.-sulfooxy-5.beta.-cholan-24-oic acid
3.alpha.-sulfate-5.beta.-cholan-24-oic acid
(r)-4-((3r,5r,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3-(sulfooxy)hexadecahydro-1h-cyclopenta(a)phenanthren-17-yl)pentanoic acid
Q27116471
st 24:1;o3;s
DTXSID901043664
AKOS040754109
PD052901

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"To test whether hepatotoxicity occurring in National Cooperative Gallstone Study patients was caused by a toxic effect of chenodiol per se or of lithocholate caused by defective sulfation, bile samples were analyzed using a new high-performance liquid chromatography method that measures the proportions of the four individual lithocholate amidates (sulfated and unsulfated lithocholylglycine and lithocholyltaurine) and all common bile acid amidates."( The lack of relationship between hepatotoxicity and lithocholic-acid sulfation in biliary bile acids during chenodiol therapy in the National Cooperative Gallstone Study.
Converse, JL; Fisher, RL; Hofmann, AF; Lan, SP; Rossi, SS, 1991
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
steroid sulfateA sulfuric ester obtained by the formal condensation of a hydroxy group of any steroid with sulfuric acid.
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Multidrug resistance-associated protein 4Homo sapiens (human)IC50 (µMol)10.00000.20005.677410.0000AID681389
Vitamin D3 receptorHomo sapiens (human)IC50 (µMol)36.65000.00000.43746.4300AID1277414; AID1277417
[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)
Vitamin D3 receptorHomo sapiens (human)EC50 (µMol)150.00000.00000.14232.1400AID1277413; AID1277415
G-protein coupled bile acid receptor 1Homo sapiens (human)EC50 (µMol)100.00000.02372.52598.9000AID324923
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (50)

Processvia Protein(s)Taxonomy
prostaglandin secretionMultidrug resistance-associated protein 4Homo sapiens (human)
cilium assemblyMultidrug resistance-associated protein 4Homo sapiens (human)
platelet degranulationMultidrug resistance-associated protein 4Homo sapiens (human)
xenobiotic metabolic processMultidrug resistance-associated protein 4Homo sapiens (human)
xenobiotic transmembrane transportMultidrug resistance-associated protein 4Homo sapiens (human)
bile acid and bile salt transportMultidrug resistance-associated protein 4Homo sapiens (human)
prostaglandin transportMultidrug resistance-associated protein 4Homo sapiens (human)
urate transportMultidrug resistance-associated protein 4Homo sapiens (human)
glutathione transmembrane transportMultidrug resistance-associated protein 4Homo sapiens (human)
transmembrane transportMultidrug resistance-associated protein 4Homo sapiens (human)
cAMP transportMultidrug resistance-associated protein 4Homo sapiens (human)
leukotriene transportMultidrug resistance-associated protein 4Homo sapiens (human)
monoatomic anion transmembrane transportMultidrug resistance-associated protein 4Homo sapiens (human)
export across plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
transport across blood-brain barrierMultidrug resistance-associated protein 4Homo sapiens (human)
guanine nucleotide transmembrane transportMultidrug resistance-associated protein 4Homo sapiens (human)
negative regulation of DNA-templated transcriptionVitamin D3 receptorHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIVitamin D3 receptorHomo sapiens (human)
cell morphogenesisVitamin D3 receptorHomo sapiens (human)
skeletal system developmentVitamin D3 receptorHomo sapiens (human)
calcium ion transportVitamin D3 receptorHomo sapiens (human)
intracellular calcium ion homeostasisVitamin D3 receptorHomo sapiens (human)
lactationVitamin D3 receptorHomo sapiens (human)
negative regulation of cell population proliferationVitamin D3 receptorHomo sapiens (human)
positive regulation of gene expressionVitamin D3 receptorHomo sapiens (human)
negative regulation of keratinocyte proliferationVitamin D3 receptorHomo sapiens (human)
positive regulation of vitamin D 24-hydroxylase activityVitamin D3 receptorHomo sapiens (human)
positive regulation of bone mineralizationVitamin D3 receptorHomo sapiens (human)
phosphate ion transmembrane transportVitamin D3 receptorHomo sapiens (human)
bile acid signaling pathwayVitamin D3 receptorHomo sapiens (human)
mRNA transcription by RNA polymerase IIVitamin D3 receptorHomo sapiens (human)
positive regulation of keratinocyte differentiationVitamin D3 receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIVitamin D3 receptorHomo sapiens (human)
decidualizationVitamin D3 receptorHomo sapiens (human)
intestinal absorptionVitamin D3 receptorHomo sapiens (human)
apoptotic process involved in mammary gland involutionVitamin D3 receptorHomo sapiens (human)
positive regulation of apoptotic process involved in mammary gland involutionVitamin D3 receptorHomo sapiens (human)
regulation of calcidiol 1-monooxygenase activityVitamin D3 receptorHomo sapiens (human)
mammary gland branching involved in pregnancyVitamin D3 receptorHomo sapiens (human)
vitamin D receptor signaling pathwayVitamin D3 receptorHomo sapiens (human)
positive regulation of vitamin D receptor signaling pathwayVitamin D3 receptorHomo sapiens (human)
response to bile acidVitamin D3 receptorHomo sapiens (human)
multicellular organism developmentVitamin D3 receptorHomo sapiens (human)
cell differentiationVitamin D3 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 (30)

Processvia Protein(s)Taxonomy
guanine nucleotide transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
protein bindingMultidrug resistance-associated protein 4Homo sapiens (human)
ATP bindingMultidrug resistance-associated protein 4Homo sapiens (human)
ABC-type xenobiotic transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
prostaglandin transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
urate transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
purine nucleotide transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
ABC-type glutathione S-conjugate transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
ABC-type bile acid transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
efflux transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
15-hydroxyprostaglandin dehydrogenase (NAD+) activityMultidrug resistance-associated protein 4Homo sapiens (human)
ATP hydrolysis activityMultidrug resistance-associated protein 4Homo sapiens (human)
glutathione transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
ATPase-coupled transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
xenobiotic transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
ATPase-coupled inorganic anion transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
ABC-type transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
DNA-binding transcription factor activityVitamin D3 receptorHomo sapiens (human)
vitamin D response element bindingVitamin D3 receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificVitamin D3 receptorHomo sapiens (human)
DNA bindingVitamin D3 receptorHomo sapiens (human)
nuclear receptor activityVitamin D3 receptorHomo sapiens (human)
protein bindingVitamin D3 receptorHomo sapiens (human)
zinc ion bindingVitamin D3 receptorHomo sapiens (human)
bile acid nuclear receptor activityVitamin D3 receptorHomo sapiens (human)
nuclear retinoid X receptor bindingVitamin D3 receptorHomo sapiens (human)
calcitriol bindingVitamin D3 receptorHomo sapiens (human)
lithocholic acid bindingVitamin D3 receptorHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingVitamin D3 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 (15)

Processvia Protein(s)Taxonomy
nucleolusMultidrug resistance-associated protein 4Homo sapiens (human)
Golgi apparatusMultidrug resistance-associated protein 4Homo sapiens (human)
plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
membraneMultidrug resistance-associated protein 4Homo sapiens (human)
basolateral plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
apical plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
platelet dense granule membraneMultidrug resistance-associated protein 4Homo sapiens (human)
external side of apical plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
nucleusVitamin D3 receptorHomo sapiens (human)
nucleusVitamin D3 receptorHomo sapiens (human)
nucleoplasmVitamin D3 receptorHomo sapiens (human)
cytosolVitamin D3 receptorHomo sapiens (human)
RNA polymerase II transcription regulator complexVitamin D3 receptorHomo sapiens (human)
chromatinVitamin D3 receptorHomo sapiens (human)
receptor complexVitamin D3 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
AID1277417Antagonist activity against VP16 tagged-VDR-LBD (unknown origin) expressed in HEK293T cells assessed as inhibition of 1,25-dihydroxyvitamin D3-induced SRC1 coactivator peptide recruitment after 16 hrs by luciferase reporter gene based two hybrid assay2016European journal of medicinal chemistry, Feb-15, Volume: 109Synthesis and evaluation of vitamin D receptor-mediated activities of cholesterol and vitamin D metabolites.
AID680587TP_TRANSPORTER: inhibition of Etoposide glucuronide uptake (Etoposide glucuronide: 0.094 uM, Lithocholic acid-sulfate: 20 uM) by Lithocholate-3-sulfate at a concentration of 20uM in membrane vesicle from MRP3-expressing Sf9 cells2003The Biochemical journal, Jan-01, Volume: 369, Issue:Pt 1
Transport of bile acids in multidrug-resistance-protein 3-overexpressing cells co-transfected with the ileal Na+-dependent bile-acid transporter.
AID680588TP_TRANSPORTER: inhibition of Etoposide glucuronide uptake (Etoposide glucuronide: 0.094 uM, LC-S: 20.0 uM) in membrane vesicles from MRP3-expressing Sf9 cells2003The Biochemical journal, Jan-01, Volume: 369, Issue:Pt 1
Transport of bile acids in multidrug-resistance-protein 3-overexpressing cells co-transfected with the ileal Na+-dependent bile-acid transporter.
AID1277414Antagonist activity against VDR-LBD (unknown origin) expressed in Escherichia coli assessed as inhibition of VDR agonist LG190178-induced SRC2-3 coactivator peptide recruitment after 30 mins by fluorescence polarization assay2016European journal of medicinal chemistry, Feb-15, Volume: 109Synthesis and evaluation of vitamin D receptor-mediated activities of cholesterol and vitamin D metabolites.
AID1277413Agonist activity at VDR-LBD (unknown origin) expressed in Escherichia coli assessed as SRC2-3 coactivator peptide recruitment after 30 mins by fluorescence polarization assay2016European journal of medicinal chemistry, Feb-15, Volume: 109Synthesis and evaluation of vitamin D receptor-mediated activities of cholesterol and vitamin D metabolites.
AID681389TP_TRANSPORTER: inhibition of E217betaG uptake in membrane vesicles from MRP4-expressing HEK-293 cells2003The Biochemical journal, Apr-15, Volume: 371, Issue:Pt 2
Steroid and bile acid conjugates are substrates of human multidrug-resistance protein (MRP) 4 (ATP-binding cassette C4).
AID1277420Cytotoxicity against HEK293T cells assessed as reduction in cell viability after 18 hrs by CellTiter-Glo luminescence assay2016European journal of medicinal chemistry, Feb-15, Volume: 109Synthesis and evaluation of vitamin D receptor-mediated activities of cholesterol and vitamin D metabolites.
AID1277415Agonist activity at VP16 tagged-VDR-LBD (unknown origin) expressed in HEK293T cells assessed as SRC1 coactivator peptide recruitment after 16 hrs by luciferase reporter gene based two hybrid assay2016European journal of medicinal chemistry, Feb-15, Volume: 109Synthesis and evaluation of vitamin D receptor-mediated activities of cholesterol and vitamin D metabolites.
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.
AID324931Agonist activity at human FXR expressed in COS1 cells at 100 uM by luciferase assay relative to 6-enantiomeric chenodeoxy cholic 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (34)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (50.00)18.7374
1990's10 (29.41)18.2507
2000's4 (11.76)29.6817
2010's3 (8.82)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: 10.67

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 Index10.67 (24.57)
Research Supply Index3.64 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.67)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (2.78%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other35 (97.22%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]