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
Cholesterol 7alpha-hydroxylase. 2. Biochemical properties and participation of endogenous cholesterol in the assay in vitro.
1975 Jun 16
Endogenous bile acids are ligands for the nuclear receptor FXR/BAR.
1999 May
Bile acids: natural ligands for an orphan nuclear receptor.
1999 May 21
Identification of a nuclear receptor for bile acids.
1999 May 21
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon.
2001 Aug 28
Modulation of inducible nitric oxide synthase expression in rat intestinal cells by colon tumor promoters.
2001 Jan
Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate.
2001 Jul
The nuclear receptor PXR is a lithocholic acid sensor that protects against liver toxicity.
2001 Mar 13
Three-dimensional structural model analysis of the binding site of lithocholic acid, an inhibitor of DNA polymerase beta and DNA topoisomerase II.
2001 Nov
Anchoring and bola cationic amphiphiles for nucleotide delivery. Effects of orientation and extension of hydrophobic regions.
2001 Nov 19
[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
Lithocholic acid decreases expression of bile salt export pump through farnesoid X receptor antagonist activity.
2002 Aug 30
Selective interaction of bile acids with muscarinic receptors: a case of molecular mimicry.
2002 Dec 20
Participation of two members of the very long-chain acyl-CoA synthetase family in bile acid synthesis and recycling.
2002 Jul 5
Postprandial changes in serum unconjugated bile acid concentrations in healthy beagles.
2002 Jun
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
Synthesis of [3,4-(13)c(2)]-enriched bile salts as NMR probes of protein-ligand interactions.
2002 Sep 20
Influence of breast feeding, and adapted and hydrolyzed formulas on biliary bile acids in newborn guinea pigs.
2003
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
Opposing effects of butyrate and bile acids on apoptosis of human colon adenoma cells: differential activation of PKC and MAP kinases.
2003 Mar 10
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
Comparison among fecal secondary bile acid levels, fecal microbiota and Clostridium scindens cell numbers in Japanese.
2004
Megalin and cubilin expression in gallbladder epithelium and regulation by bile acids.
2004 Dec
A nonenzymatic modification of the amino-terminal domain of histone H3 by bile acid acyl adenylate.
2004 Dec 31
Cholesterol-lowering properties of Ganoderma lucidum in vitro, ex vivo, and in hamsters and minipigs.
2004 Feb 18
Structural determinants for vitamin D receptor response to endocrine and xenobiotic signals.
2004 Jan
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
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
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