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Structure Database (LMSD)

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Common Name

Allolithocholic acid

Systematic Name

3α-Hydroxy-5α-cholan-24-oic Acid

Synonyms

AlloLCA

LM ID

LMST04010005

Formula

C₂₄H₄₀O₃

Exact Mass

Calculate m/z

376.297745

Sum Composition

ST 24:1;O3

Status

Curated

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Classification

Biological Context

Allolithocholic acid is a secondary allomonohydroxy bile acid.¹ It activates large-conductance calcium-activated potassium channels (BK/KCas; EC50 = 44.21 µM in Xenopus oocytes expressing the rat channel). Fecal levels of allolithocholic acid are increased in patients with colorectal cancer.² Allolithocholic acid has also been found in the urine of infants with biliary atresia.³

This information has been provided by Cayman Chemical

References

1. Tadano, T., Kanoh, M., Kondoh, H., et al. Kinetic analysis of bile acids in the feces of colorectal cancer patients by gas chromatography-mass spectrometry (GC-MS). Rinsho Byori. 55(5), 417-427 (2007).

2. Makino, I., Sjövall, J., Norman, A., et al. Excretion of 3β-hydroxy-5-cholenoic and 3ɑ-hydroxy-5ɑ-cholanoic acids in urine of infants with biliary atresia. FEBS Lett. 15(2), 161-164 (1971).

3. Bukiya, A.N., McMillan, J., Parrill, A.L., et al. Structural determinants of monohydroxylated bile acids to activate β1 subunit-containing BK channels. J. Lipid Res. 49(11), 2441-2451 (2008).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry.,
J Lipid Res, 1977

Pubmed ID: 864325

String Representations

InChiKey (Click to copy)

SMEROWZSTRWXGI-NWFSOSCSSA-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