lithocholic acid

Also known as LCA, lithocholate, (3alpha,5beta)-3-hydroxycholan-24-oic acid, 5beta-cholanic acid-3alpha-ol, 3alpha-hydroxy-5beta-cholanoic acid, 3alpha-hydroxy-5beta-cholanic acid, 3alpha-Hydroxy-5beta-cholanate, (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]valeric acid

chemical compound

Chemical data

Formula: C24H40O3
Molecular weight: 376.6 g/mol
IUPAC name: (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C
InChIKey: SMEROWZSTRWXGI-HVATVPOCSA-N
XLogP: 6.3
Polar surface area: 57.5 Å²
H-bond donors: 2
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

2,707 papers

Lithocholic Acid, Calorie Restriction, and Halting Aging.Advanced biology · 2025
Lithocholic Acid Species: Metabolism, Signaling Pathways, and Clinical Significance in Enterohepatic Diseases.International journal of molecular sciences · 2025
Lithocholic acid ameliorates ulcerative colitis via the PXR/TLR4/NF-κB/NLRP3 signaling pathway and gut microbiota modulation.Cellular and molecular life sciences : CMLS · 2025
Lithocholic Acid Amides as Potent Vitamin D Receptor Agonists.Biomolecules · 2022
Allo-lithocholic acid, a microbiome derived secondary bile acid, attenuates liver fibrosis.Biochemical pharmacology · 2025

via PubMed

Wikidata facts

Subclass of: sterol
Mass: 376.298
Has use: detergent

Show 6 more facts

chemical formula: C₂₄H₄₀O₃
canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C
physically interacts with: vitamin D receptor
found in taxon: house mouse
Commons category: Lithocholic acid

Sources (4)

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