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
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
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 |
|---|---|---|
| Cholesterol 7alpha-hydroxylase. 2. Biochemical properties and participation of endogenous cholesterol in the assay in vitro. | 1975 Jun 16 |
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| LUV's lipid composition modulates diffusion of bile acids. | 2001 Apr |
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| Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon. | 2001 Aug 28 |
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| Alterations in intestinal microflora, faecal bile acids and short chain fatty acids in dextran sulphate sodium-induced experimental acute colitis in rats. | 2001 Feb |
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| Application of photoaffinity labeling with [(3)H] all trans- and 9-cis-retinoic acids for characterization of cellular retinoic acid--binding proteins I and II. | 2001 Jan |
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| Fetal bile acid metabolism: analysis of urinary 3beta-monohydroxy-delta(5) bile acid in preterm infants. | 2001 Jul |
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| Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate. | 2001 Jul |
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| [Other antihyperlipidemic drugs with novel mechanism]. | 2001 Mar |
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| The nuclear receptor PXR is a lithocholic acid sensor that protects against liver toxicity. | 2001 Mar 13 |
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| Three-dimensional structural model analysis of the binding site of lithocholic acid, an inhibitor of DNA polymerase beta and DNA topoisomerase II. | 2001 Nov |
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| Anchoring and bola cationic amphiphiles for nucleotide delivery. Effects of orientation and extension of hydrophobic regions. | 2001 Nov 19 |
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| Carrier-mediated delivery improves the efficacy of 9-(2-phosphonylmethoxyethyl)adenine against hepatitis B virus. | 2001 Sep |
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| Photoaffinity labeling of human retinoid X receptor beta (RXRbeta) with 9-cis-retinoic acid: identification of phytanic acid, docosahexaenoic acid, and lithocholic acid as ligands for RXRbeta. | 2002 Apr 16 |
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| Lithocholic acid decreases expression of bile salt export pump through farnesoid X receptor antagonist activity. | 2002 Aug 30 |
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| Nuclear xeno-sensors as receptors for cholestatic bile acids: the second line of defense. | 2002 Jan |
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| Postprandial changes in serum unconjugated bile acid concentrations in healthy beagles. | 2002 Jun |
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| A prospective study of serum bile acid concentrations and colorectal cancer risk in post-menopausal women on the island of Guernsey. | 2002 Jun 5 |
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| Unconjugated bile acids modulate adult and neonatal neutrophil chemotaxis induced in vitro by N-formyl-met-leu-phe-peptide. | 2002 Mar |
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| Rapid and improved method for the determination of bile acids in human feces using MS. | 2002 Nov |
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| The effect of charge reversal mutations in the alpha-helical region of liver fatty acid binding protein on the binding of fatty-acyl CoAs, lysophospholipids and bile acids. | 2002 Oct |
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| Regulation of a xenobiotic sulfonation cascade by nuclear pregnane X receptor (PXR). | 2002 Oct 15 |
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| Bile acids stimulate invasion and haptotaxis in human colorectal cancer cells through activation of multiple oncogenic signaling pathways. | 2002 Oct 3 |
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| Functional interaction of lithocholic acid conjugates with M3 muscarinic receptors on a human colon cancer cell line. | 2002 Oct 9 |
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| Calcium affects biomarkers of colon carcinogenesis after right hemicolectomy. | 2002 Sep |
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| Intestinal bile acids can bind to and activate the vitamin D receptor. | 2002 Sep |
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| Kinetic characterization of native and cysteine 112-modified glutathione S-transferase A1-1: reassessment of nonsubstrate ligand binding. | 2002 Sep 10 |
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| Does ursodeoxycholic acid change the proliferation of the colorectal mucosa?. A randomized, placebo-controlled study. | 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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| Activation of muscarinic receptor signaling by bile acids: physiological and medical implications. | 2003 Aug |
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| Synthesis of ester-linked lithocholic acid dimers. | 2003 Dec |
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| Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone. | 2003 Feb 1 |
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| Glucosidation of hyodeoxycholic acid by UDP-glucuronosyltransferase 2B7. | 2003 Feb 1 |
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| Identification of an endogenous ligand that activates pregnane X receptor-mediated sterol clearance. | 2003 Feb 4 |
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| [Functional analysis of drug metabolizing enzymes using gene knockout animals]. | 2003 Jul |
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| New insights into the mechanisms of vitamin D action. | 2003 Mar 1 |
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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 Mar 10 |
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| A G protein-coupled receptor responsive to bile acids. | 2003 Mar 14 |
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| Induction of ABCC3 (MRP3) by pregnane X receptor activators. | 2003 Nov |
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| 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 Oct |
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| Bile acid amidoalcohols: simple organogelators. | 2004 Dec 15 |
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| A novel constitutive androstane receptor-mediated and CYP3A-independent pathway of bile acid detoxification. | 2004 Feb |
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| Cholesterol-lowering properties of Ganoderma lucidum in vitro, ex vivo, and in hamsters and minipigs. | 2004 Feb 18 |
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| Structural determinants for vitamin D receptor response to endocrine and xenobiotic signals. | 2004 Jan |
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| Structure-activity relationship of bile acids and bile acid analogs in regard to FXR activation. | 2004 Jan |
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| Feed-forward regulation of bile acid detoxification by CYP3A4: studies in humanized transgenic mice. | 2004 Mar 19 |
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| The farnesoid X receptor controls gene expression in a ligand- and promoter-selective fashion. | 2004 Mar 5 |
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| Detoxification of lithocholic acid, a toxic bile acid: relevance to drug hepatotoxicity. | 2004 Oct |
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| Selective activation of vitamin D receptor by lithocholic acid acetate, a bile acid derivative. | 2005 Jan |
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| Affinity capture of a mammalian DNA polymerase beta by inhibitors immobilized to resins used in solid-phase organic synthesis. | 2005 Jan-Feb |
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| Vitamin D receptor-dependent regulation of colon multidrug resistance-associated protein 3 gene expression by bile acids. | 2005 Jun 17 |
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
Fri Dec 15 19:09:31 GMT 2023
by
admin
on
Fri Dec 15 19:09:31 GMT 2023
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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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LITHOCHOLIC ACID
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TRANSPORTER -> INHIBITOR |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT |
IN VITRO
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PARENT -> METABOLITE |
FECAL
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
MAJOR
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METABOLITE -> PARENT |
IN VITRO
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PARENT -> METABOLITE TOXIC |
IN-VIVO
FECAL
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (TLC)
EP
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