| Lithocholic acid, also known as 3α-hydroxy-5β-cholan-24-oic acid or LCA, is a bile acid that acts as a detergent to solubilize fats for absorption. Bacterial action in the colon produces LCA from chenodeoxycholic acid by reduction of the hydroxyl functional group at carbon-7 in the "B" ring of the steroid framework.
It has been implicated in human and experimental animal carcinogenesis. Preliminary in vitro research suggests that LCA selectively kills neuroblastoma cells, while sparing normal neuronal cells and is cytotoxic to numerous other malignant cell types at physiologically relevant concentrations.
Dietary fiber can bind to lithocholic acid and aid in its excretion in stool; as such, fiber can protect against colon cancer.
LCA (and LCA acetate and LCA propionate) can activate the vitamin D receptor without raising calcium levels as much as vitamin D itself.
LCA binds with 20 μM affinity to the human membrane enzyme NAPE-PLD, enhancing dimer assembly and enabling catalysis. NAPE-PLD catalyzes the release of anandamide and other N-acylethanolamines (NAE) from the membrane precursor N-acylphosphatidylethanolamine (NAPE). NAPE-PLD facilitates crosstalk between bile acid signals and lipid amide signals.
LCA has been reported to have anti-aging effects in yeast, and more recently fruit flies, nematodes, and mice. |
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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 |
| SMEROWZSTRWXGI-HVATVPOCSA-N |
| [H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@]([H])(CC[C@@]34[H])[C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@H](O)C2 |
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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View more via ChEBI Ontology
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3α-hydroxy-5β-cholan-24-oic acid
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(3α,5β)-3-hydroxycholan-24-oic acid
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ChemIDplus
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3alpha-Hydroxy-5beta-cholanate
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KEGG COMPOUND
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3alpha-Hydroxy-5beta-cholanic acid
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KEGG COMPOUND
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3α-hydroxy-5β-cholanic acid
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NIST Chemistry WebBook
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3α-hydroxy-5β-cholanoic acid
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NIST Chemistry WebBook
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5β-cholanic acid-3α-ol
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NIST Chemistry WebBook
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Lithocholic acid
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KEGG COMPOUND
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3217757
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Reaxys Registry Number
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Reaxys
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434-13-9
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CAS Registry Number
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NIST Chemistry WebBook
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434-13-9
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CAS Registry Number
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ChemIDplus
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