Lithocholic acid

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.^{[citation needed]}

Lithocholic acid^[1]

Names
IUPAC name 3α-Hydroxy-5β-cholan-24-oic acid
Systematic IUPAC name (4R)-4-[(1R,3aS,3bR,5aR,7R,9aS,9bS,11aR)-7-Hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
Other names Lithocholate; Lithocolic acid; 3α-Hydroxy-5β-cholanic acid; 5β-Cholan-24-oic acid-3α-ol
Identifiers
CAS Number	434-13-9 Y
3D model (JSmol)	Interactive image
Beilstein Reference	3217757
ChEBI	CHEBI:16325 Y
ChEMBL	ChEMBL1478 Y
ChemSpider	9519 Y
ECHA InfoCard	100.006.455
EC Number	207-099-1
IUPHAR/BPS	611
KEGG	C03990
PubChem CID	9903
RTECS number	FZ2275000
UNII	5QU0I8393U Y
CompTox Dashboard (EPA)	DTXSID6020779
InChI 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 Y Key: SMEROWZSTRWXGI-HVATVPOCSA-N Y InChI=1/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 Key: SMEROWZSTRWXGI-HVATVPOCBI
SMILES O=C(O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]4[C@H]2CC[C@@H]3C[C@H](O)CC[C@@]34C)C
Properties
Chemical formula	C24H40O3
Molar mass	376.581 g·mol−1
Melting point	183 to 188 °C (361 to 370 °F; 456 to 461 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

It has been implicated in human and experimental animal carcinogenesis.^[2][3] 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.^[4]

Dietary fiber can bind to lithocholic acid and aid in its excretion in stool;^[5] 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.^[6]

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.^[7][8][9]

LCA has been reported to have anti-aging effects in yeast,^[10][11][12] and more recently fruit flies, nematodes, and mice.^[13][14]