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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
Structure of LITHOCHOLIC ACID

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

HIDE SMILES / InChI

Molecular Formula C24H40O3
Molecular Weight 376.5726
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

PubMed

PubMed

TitleDatePubMed
Effects of bile acids on proliferation and production of proteinase activity of Uronema marinum (Ciliophora: Scuticociliatida).
2004 Dec 13
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
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 Vitro Use Guide
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 Tue Mar 06 11:49:24 UTC 2018
Edited
by admin
on Tue Mar 06 11:49:24 UTC 2018
Record UNII
5QU0I8393U
Record Status Validated (UNII)
Record Version
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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
LITHOCHOLIC ACID [HSDB]
Common Name English
NSC-657956
Code English
Code System Code Type Description
CAS
434-13-9
Created by admin on Tue Mar 06 11:49:24 UTC 2018 , Edited by admin on Tue Mar 06 11:49:24 UTC 2018
PRIMARY
MERCK INDEX
M6871
Created by admin on Tue Mar 06 11:49:24 UTC 2018 , Edited by admin on Tue Mar 06 11:49:24 UTC 2018
PRIMARY Merck Index
HSDB
434-13-9
Created by admin on Tue Mar 06 11:49:24 UTC 2018 , Edited by admin on Tue Mar 06 11:49:24 UTC 2018
PRIMARY
ECHA (EC/EINECS)
207-099-1
Created by admin on Tue Mar 06 11:49:24 UTC 2018 , Edited by admin on Tue Mar 06 11:49:24 UTC 2018
PRIMARY
WIKIPEDIA
LITHOCHOLIC ACID
Created by admin on Tue Mar 06 11:49:24 UTC 2018 , Edited by admin on Tue Mar 06 11:49:24 UTC 2018
PRIMARY
MESH
D008095
Created by admin on Tue Mar 06 11:49:24 UTC 2018 , Edited by admin on Tue Mar 06 11:49:24 UTC 2018
PRIMARY
EPA CompTox
434-13-9
Created by admin on Tue Mar 06 11:49:24 UTC 2018 , Edited by admin on Tue Mar 06 11:49:24 UTC 2018
PRIMARY
PUBCHEM
9903
Created by admin on Tue Mar 06 11:49:24 UTC 2018 , Edited by admin on Tue Mar 06 11:49:24 UTC 2018
PRIMARY SWITZERF
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