Structure Database (LMSD)

Common Name
Lithocholic acid
Systematic Name
3α-Hydroxy-5β-cholan-24-oic Acid
Synonyms
  • 3alpha-hydroxy Cholanic Acid
  • LCA
  • Lithocholate
LM ID
LMST04010003
Formula
Exact Mass
Calculate m/z
376.297745
Sum Composition
Status
Curated





Classification

Biological Context

Lithocholic acid is a secondary bile acid that has been shown to cause cholestasis in animal models and has also been implicated in carcinogenesis.1,2 It is produced from chenodeoxycholic acid by bacterial action in the colon and can be conjugated with glycine or taurine. Whereas in normal colonic epithelium lithocholic acid promotes apoptosis, it has been shown to suppress apoptosis in pre-malignant colonic epithelium in the presence of a carcinogen.3 Lithocholic acid can activate the pregnane X receptor and the vitamin D receptor, which may serve as a biological sensor to regulate lithocholic acid-induced toxicity.2,4,5

This information has been provided by Cayman Chemical

References

1. Makishima, M., Lu, T.T., Xie, W., et al. Vitamin D receptor as an intestinal bile acid sensor. Science 296(5571), 1313-1316 (2002).
2. Tan, K.P., Yang, M., and Ito, S. Activation of nuclear factor (erythroid-2 like) factor 2 by toxic bile acids provokes adaptive defense responses to enhance cell survival at the emergence of oxidative stress. Mol. Pharmacol. 72(5), 1380-1390 (2007).
5. Staudinger, J.L., Goodwin, B., Jones, S.A., et al. The nuclear receptor PXR is a lithocholic acid sensor that protects against liver toxicity. Proc. Natl. Acad. Sci. USA 98(6), 3369-3374 (2000).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Naturally Occurring Bile Acids and Alcohols and Their Origins,
The Bile Acids Chemistry, Physiology, and Metabolism, 1971

String Representations

InChiKey (Click to copy)
SMEROWZSTRWXGI-HVATVPOCSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(O)=O)CC[C@@]4([H])[C@]3([H])CC[C@]2([H])C[C@H](O)C1

Other Databases

KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
BBA0003
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 4
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 398.05
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.79
Molar Refractivity 107.77

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Created at
-
Updated at
1st Mar 2024