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Structure Database (LMSD)

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Common Name

Allocholic acid

Systematic Name

3α,7α,12α-Trihydroxy-5α-cholan-24-oic Acid

Synonyms

ACA
AlloCA

LM ID

LMST04010092

Formula

C₂₄H₄₀O₅

Exact Mass

Calculate m/z

408.287575

Sum Composition

ST 24:1;O5

Status

Curated

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Classification

Biological Context

Allocholic acid is a bile acid and an isomer of cholic acid .¹ It is typically produced in the fetal or larval stages of development but has been found in adult mammals in the context of cancer or during liver regeneration in rats.^1,2 Allocholic acid is a precursor to petromyzonol , a bile acid of larval sea lamprey that acts as a migratory pheromone.³ The levels of allocholic acid are elevated in the plasma of mdr2-/- mice, a model of bile duct inflammation leading to hepatocellular carcinoma.⁴

This information has been provided by Cayman Chemical

References

1. Mendoza, M.E., Monte, M.J., Serrano, M.A., et al. Physiological characteristics of allo-cholic acid. J. Lipid Res. 44(1), 84-92 (2003).

2. Monte, M.J., Martinez-Diez, M.C., El-Mir, M.Y., et al. Changes in the pool of bile acids in hepatocyte nuclei during rat liver regeneration. J. Hepatol. 36(4), 534-542 (2002).

3. Han, J., Liu, Y., Wang, R., et al. Metabolic profiling of bile acids in human and mouse blood by LC-MS/MS in combination with phospholipid-depletion solid-phase extraction. Anal. Chem. 87(2), 1127-1136 (2015).

4. Gandre-Babbe, S., and van der Bliek, A.M. The novel tail-anchored membrane protein Mff controls mitochondrial and peroxisomal fission in mammalian cells. Mol. Biol. Cell 19(6), 2402-2412 (2008).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

BILE ACIDS. XXII. ALLOCHOLIC ACID, A METABOLITE OF 5-ALPHA-CHOLESTAN-3-BET-A-OL IN THE RAT.,
J Biol Chem, 1965

Pubmed ID: 14285492

String Representations

InChiKey (Click to copy)

BHQCQFFYRZLCQQ-PGHAKIONSA-N

InChi (Click to copy)

InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])C[C@H](O)[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(O)=O)CC[C@@]4([H])[C@]3([H])[C@H](O)C[C@@]2([H])C[C@H](O)C1