Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C24H40O3 |
| Molecular Weight | 376.5726 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI
InChIKey=SMEROWZSTRWXGI-HVATVPOCSA-N
InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1
| Molecular Formula | C24H40O3 |
| Molecular Weight | 376.5726 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Lithocholic acid (LCA) is a secondary bile acid that is formed in the intestine by the bacteria and can activate the pregnane X and the vitamin D receptors. In humans, elevated levels of LCA are found in patients suffering from the chronic cholestatic liver disease. Whereas in normal colonic epithelium lithocholic acid promotes apoptosis, it has been shown to possess anti-tumor effect in human neuroblastoma cell lines. In addition, was proposed, that LCA could kill cancer cells and increase the longevity of non-cancerous cells by causing quite opposite effects on the same kind of mitochondria-confined processes in these two different cell types.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: O75469|||Q9UJ26 Gene ID: 8856.0 Gene Symbol: NR1I2 Target Organism: Homo sapiens (Human) |
|||
Target ID: P11473 Gene ID: 7421.0 Gene Symbol: VDR Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Diagnostic | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Lithocholic acid decreases expression of UGT2B7 in Caco-2 cells: a potential role for a negative farnesoid X receptor response element. | 2005-07 |
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| Vitamin D receptor-dependent regulation of colon multidrug resistance-associated protein 3 gene expression by bile acids. | 2005-06-17 |
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| Molecular and functional comparison of 1,25-dihydroxyvitamin D(3) and the novel vitamin D receptor ligand, lithocholic acid, in activating transcription of cytochrome P450 3A4. | 2005-04-01 |
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| Generation of a single-chain Fv fragment for the monitoring of deoxycholic acid residues anchored on endogenous proteins. | 2005-04 |
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| Chemical synthesis of 24-beta-D-galactopyranosides of bile acids: a new type of bile acid conjugates in human urine. | 2005-04 |
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| Novel pathways of bile acid metabolism involving CYP3A4. | 2005-02-21 |
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| Affinity capture of a mammalian DNA polymerase beta by inhibitors immobilized to resins used in solid-phase organic synthesis. | 2005-01-20 |
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| Combined loss of orphan receptors PXR and CAR heightens sensitivity to toxic bile acids in mice. | 2005-01 |
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| Selective activation of vitamin D receptor by lithocholic acid acetate, a bile acid derivative. | 2005-01 |
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| Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. | 2005-01 |
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| Properties of a thermostable extracellular lipase from Bacillus megaterium AKG-1. | 2005 |
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| A nonenzymatic modification of the amino-terminal domain of histone H3 by bile acid acyl adenylate. | 2004-12-31 |
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| Determination of underivatised sterols and bile acid trimethyl silyl ether methyl esters by gas chromatography-mass spectrometry-single ion monitoring in faeces. | 2004-12-25 |
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| Bile acid amidoalcohols: simple organogelators. | 2004-12-15 |
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| Effects of bile acids on proliferation and production of proteinase activity of Uronema marinum (Ciliophora: Scuticociliatida). | 2004-12-13 |
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| Megalin and cubilin expression in gallbladder epithelium and regulation by bile acids. | 2004-12 |
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| The constitutive androstane receptor and pregnane X receptor function coordinately to prevent bile acid-induced hepatotoxicity. | 2004-11-19 |
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| Modified oligonucleotides containing lithocholic acid in their backbones: their enhanced cellular uptake and their mimicking of hairpin structures. | 2004-11-05 |
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| Steroid and lipid conjugates of siRNAs to enhance cellular uptake and gene silencing in liver cells. | 2004-10-04 |
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| Detoxification of lithocholic acid, a toxic bile acid: relevance to drug hepatotoxicity. | 2004-10 |
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| DNA hypomethylation induced by non-genotoxic carcinogens in mouse and rat colon. | 2004-08-30 |
|
| Structural relationship of lithocholic acid derivatives binding to the N-terminal 8-kDa domain of DNA polymerase beta. | 2004-08-24 |
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| Crystallographic and solution studies of N-lithocholyl insulin: a new generation of prolonged-acting human insulins. | 2004-05-25 |
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| Feed-forward regulation of bile acid detoxification by CYP3A4: studies in humanized transgenic mice. | 2004-03-19 |
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| The farnesoid X receptor controls gene expression in a ligand- and promoter-selective fashion. | 2004-03-05 |
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| Cholesterol-lowering properties of Ganoderma lucidum in vitro, ex vivo, and in hamsters and minipigs. | 2004-02-18 |
|
| A novel constitutive androstane receptor-mediated and CYP3A-independent pathway of bile acid detoxification. | 2004-02 |
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| Structural determinants for vitamin D receptor response to endocrine and xenobiotic signals. | 2004-01 |
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| Structure-activity relationship of bile acids and bile acid analogs in regard to FXR activation. | 2004-01 |
|
| Comparison among fecal secondary bile acid levels, fecal microbiota and Clostridium scindens cell numbers in Japanese. | 2004 |
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| Sex steroid receptors, secondary bile acids and colorectal cancer. A possible mechanism of interaction. | 2003-12 |
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| Synthesis of ester-linked lithocholic acid dimers. | 2003-12 |
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| Induction of ABCC3 (MRP3) by pregnane X receptor activators. | 2003-11 |
|
| Effect of tartaric acid and dietary fibre from sun-dried raisins on colonic function and on bile acid and volatile fatty acid excretion in healthy adults. | 2003-10 |
|
| Activation of muscarinic receptor signaling by bile acids: physiological and medical implications. | 2003-08 |
|
| [Functional analysis of drug metabolizing enzymes using gene knockout animals]. | 2003-07 |
|
| Protective role of hydroxysteroid sulfotransferase in lithocholic acid-induced liver toxicity. | 2003-05-16 |
|
| Effects on cell proliferation, activator protein-1 and genotoxicity by fecal water from patients with colorectal adenomas. | 2003-05 |
|
| A G protein-coupled receptor responsive to bile acids. | 2003-03-14 |
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| Opposing effects of butyrate and bile acids on apoptosis of human colon adenoma cells: differential activation of PKC and MAP kinases. | 2003-03-10 |
|
| New insights into the mechanisms of vitamin D action. | 2003-03-01 |
|
| Identification of an endogenous ligand that activates pregnane X receptor-mediated sterol clearance. | 2003-02-04 |
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| Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone. | 2003-02-01 |
|
| Glucosidation of hyodeoxycholic acid by UDP-glucuronosyltransferase 2B7. | 2003-02-01 |
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| Does ursodeoxycholic acid change the proliferation of the colorectal mucosa?. A randomized, placebo-controlled study. | 2003 |
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| Urinary excretion of bile acids in bile duct-ligated rats. | 2003 |
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| Influence of breast feeding, and adapted and hydrolyzed formulas on biliary bile acids in newborn guinea pigs. | 2003 |
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| Rapid and improved method for the determination of bile acids in human feces using MS. | 2002-11 |
|
| Intrahepatic cholestasis of pregnancy: changes in maternal-fetal bile acid balance and improvement by ursodeoxycholic acid. | 2002-01-02 |
|
| [Features of composition of bile acids in duodenal bile in patients with chronic pancreatitis]. | 2002 |
Sample Use Guides
It was discovered, that at concentrations that were not cytotoxic to primary cultures of human neurons, lithocholic acid (LCA) killed the neuroblastoma (NB) cell lines BE(2)-m17, SK-n-SH, SK-n-MCIXC and Lan-1. In BE(2)-m17, SK-n-SH and SK-n-MCIXC cells, the LCA anti-tumor effect was due to apoptotic cell death. In contrast, the LCA-triggered death of Lan-1 cells was not caused by apoptosis. It was found that LCA (0-250 uM) significantly increases the activity of caspase-8 in BE(2)-m17 and SK-n-MCIXC. The extent to which caspase-8 was activated by LCA in these two cell lines was correlated with the degree of their sensitivity to the cytotoxic, apoptosis-inducing and hydrogen peroxide-sensitizing effects of LCA. It was proposed that the LCA-dependent activation of caspase-8 seen in BE(2)-m17 and SK-n-MCIXC cells could be responsible not only for the direct proteolytic activation of caspase-3 but also for MOMP (perhaps, due to BID cleavage by caspase-8) and the resulting initiation of the intrinsic apoptotic death pathway observed in these NB cells.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:33:52 GMT 2025
by
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on
Mon Mar 31 19:33:52 GMT 2025
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| Record UNII |
5QU0I8393U
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| Record Status |
Validated (UNII)
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| Record Version |
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE |
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PARENT -> METABOLITE | |||
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METABOLITE -> PARENT |
IN VITRO
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PARENT -> METABOLITE TOXIC | |||
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (TLC)
EP
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