U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H40O3
Molecular Weight 376.5735
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LITHOCHOLIC ACID

SMILES

C[C@]([H])(CCC(=O)O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)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

HIDE SMILES / InChI

Molecular Formula C24H40O3
Molecular Weight 376.5735
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

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Features of composition of bile acids in duodenal bile in patients with chronic pancreatitis].
2002
Advantages of in vitro cytotoxicity testing by using primary rat hepatocytes in comparison with established cell lines.
2002 Aug
Selective interaction of bile acids with muscarinic receptors: a case of molecular mimicry.
2002 Dec 20
Intrahepatic cholestasis of pregnancy: changes in maternal-fetal bile acid balance and improvement by ursodeoxycholic acid.
2002 Jan-Mar
Rapid and improved method for the determination of bile acids in human feces using MS.
2002 Nov
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
Lithocholylcholine, a bile acid/acetylcholine hybrid, is a muscarinic receptor antagonist.
2002 Oct
Bile acids stimulate invasion and haptotaxis in human colorectal cancer cells through activation of multiple oncogenic signaling pathways.
2002 Oct 3
Calcium affects biomarkers of colon carcinogenesis after right hemicolectomy.
2002 Sep
Intestinal bile acids can bind to and activate the vitamin D receptor.
2002 Sep
Does ursodeoxycholic acid change the proliferation of the colorectal mucosa?. A randomized, placebo-controlled study.
2003
Urinary excretion of bile acids in bile duct-ligated rats.
2003
Influence of breast feeding, and adapted and hydrolyzed formulas on biliary bile acids in newborn guinea pigs.
2003
Sex steroid receptors, secondary bile acids and colorectal cancer. A possible mechanism of interaction.
2003 Dec
Synthesis of ester-linked lithocholic acid dimers.
2003 Dec
Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone.
2003 Feb 1
Glucosidation of hyodeoxycholic acid by UDP-glucuronosyltransferase 2B7.
2003 Feb 1
Identification of an endogenous ligand that activates pregnane X receptor-mediated sterol clearance.
2003 Feb 4
New insights into the mechanisms of vitamin D action.
2003 Mar 1
Opposing effects of butyrate and bile acids on apoptosis of human colon adenoma cells: differential activation of PKC and MAP kinases.
2003 Mar 10
A G protein-coupled receptor responsive to bile acids.
2003 Mar 14
Protective role of hydroxysteroid sulfotransferase in lithocholic acid-induced liver toxicity.
2003 May 16
Comparison among fecal secondary bile acid levels, fecal microbiota and Clostridium scindens cell numbers in Japanese.
2004
Structural relationship of lithocholic acid derivatives binding to the N-terminal 8-kDa domain of DNA polymerase beta.
2004 Aug 24
DNA hypomethylation induced by non-genotoxic carcinogens in mouse and rat colon.
2004 Aug 30
Megalin and cubilin expression in gallbladder epithelium and regulation by bile acids.
2004 Dec
Effects of bile acids on proliferation and production of proteinase activity of Uronema marinum (Ciliophora: Scuticociliatida).
2004 Dec 13
Bile acid amidoalcohols: simple organogelators.
2004 Dec 15
Determination of underivatised sterols and bile acid trimethyl silyl ether methyl esters by gas chromatography-mass spectrometry-single ion monitoring in faeces.
2004 Dec 25
A nonenzymatic modification of the amino-terminal domain of histone H3 by bile acid acyl adenylate.
2004 Dec 31
A novel constitutive androstane receptor-mediated and CYP3A-independent pathway of bile acid detoxification.
2004 Feb
Cholesterol-lowering properties of Ganoderma lucidum in vitro, ex vivo, and in hamsters and minipigs.
2004 Feb 18
Feed-forward regulation of bile acid detoxification by CYP3A4: studies in humanized transgenic mice.
2004 Mar 19
The farnesoid X receptor controls gene expression in a ligand- and promoter-selective fashion.
2004 Mar 5
Crystallographic and solution studies of N-lithocholyl insulin: a new generation of prolonged-acting human insulins.
2004 May 25
The constitutive androstane receptor and pregnane X receptor function coordinately to prevent bile acid-induced hepatotoxicity.
2004 Nov 19
Modified oligonucleotides containing lithocholic acid in their backbones: their enhanced cellular uptake and their mimicking of hairpin structures.
2004 Nov 5
Detoxification of lithocholic acid, a toxic bile acid: relevance to drug hepatotoxicity.
2004 Oct
Steroid and lipid conjugates of siRNAs to enhance cellular uptake and gene silencing in liver cells.
2004 Oct 4
Properties of a thermostable extracellular lipase from Bacillus megaterium AKG-1.
2005
Generation of a single-chain Fv fragment for the monitoring of deoxycholic acid residues anchored on endogenous proteins.
2005 Apr
Chemical synthesis of 24-beta-D-galactopyranosides of bile acids: a new type of bile acid conjugates in human urine.
2005 Apr
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 Apr 1
Novel pathways of bile acid metabolism involving CYP3A4.
2005 Feb 21
Combined loss of orphan receptors PXR and CAR heightens sensitivity to toxic bile acids in mice.
2005 Jan
Selective activation of vitamin D receptor by lithocholic acid acetate, a bile acid derivative.
2005 Jan
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump.
2005 Jan
Affinity capture of a mammalian DNA polymerase beta by inhibitors immobilized to resins used in solid-phase organic synthesis.
2005 Jan-Feb
Lithocholic acid decreases expression of UGT2B7 in Caco-2 cells: a potential role for a negative farnesoid X receptor response element.
2005 Jul
Vitamin D receptor-dependent regulation of colon multidrug resistance-associated protein 3 gene expression by bile acids.
2005 Jun 17
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Sat Jun 26 03:18:08 UTC 2021
Edited
by admin
on Sat Jun 26 03:18:08 UTC 2021
Record UNII
5QU0I8393U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LITHOCHOLIC ACID
HSDB   MI  
Common Name English
LITHOCHOLIC ACID [MI]
Common Name English
3.ALPHA.-HYDROXYCHOLANIC ACID
Systematic Name English
17.BETA.-(1-METHYL-3-CARBOXYPROPYL)ETIOCHOLAN-3.ALPHA.-OL
Common Name English
NSC-683770
Code English
URSODEOXYCHOLIC ACID IMPURITY C [EP]
Common Name English
LITHOCHOLIC ACID [HSDB]
Common Name English
LITHOCHOLIC ACID [EP]
Common Name English
NSC-657956
Code English
Code System Code Type Description
CAS
434-13-9
Created by admin on Sat Jun 26 03:18:08 UTC 2021 , Edited by admin on Sat Jun 26 03:18:08 UTC 2021
PRIMARY
MERCK INDEX
M6871
Created by admin on Sat Jun 26 03:18:08 UTC 2021 , Edited by admin on Sat Jun 26 03:18:08 UTC 2021
PRIMARY Merck Index
HSDB
4113
Created by admin on Sat Jun 26 03:18:08 UTC 2021 , Edited by admin on Sat Jun 26 03:18:08 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-099-1
Created by admin on Sat Jun 26 03:18:08 UTC 2021 , Edited by admin on Sat Jun 26 03:18:08 UTC 2021
PRIMARY
WIKIPEDIA
LITHOCHOLIC ACID
Created by admin on Sat Jun 26 03:18:08 UTC 2021 , Edited by admin on Sat Jun 26 03:18:08 UTC 2021
PRIMARY
MESH
D008095
Created by admin on Sat Jun 26 03:18:08 UTC 2021 , Edited by admin on Sat Jun 26 03:18:08 UTC 2021
PRIMARY
EPA CompTox
434-13-9
Created by admin on Sat Jun 26 03:18:08 UTC 2021 , Edited by admin on Sat Jun 26 03:18:08 UTC 2021
PRIMARY
PUBCHEM
9903
Created by admin on Sat Jun 26 03:18:08 UTC 2021 , Edited by admin on Sat Jun 26 03:18:08 UTC 2021
PRIMARY
FDA UNII
5QU0I8393U
Created by admin on Sat Jun 26 03:18:08 UTC 2021 , Edited by admin on Sat Jun 26 03:18:08 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
IN VITRO
PARENT -> METABOLITE
FECAL
PARENT -> METABOLITE TOXIC
IN-VIVO
FECAL
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
MAJOR
METABOLITE -> PARENT
IN VITRO
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
EP