Structure Database (LMSD)

Common Name
Alloisolithocholic Acid
Systematic Name
3β-Hydroxy-5α-cholan-24-oic Acid
Synonyms
  • Isoallolithocholic Acid
LM ID
LMST04010006
Formula
Exact Mass
Calculate m/z
376.297745
Sum Composition
Status
Curated



Classification

Biological Context

Alloisolithocholic acid is a metabolite of the secondary bile acid metabolite 3-oxo lithocholic acid (dehydrolithocholic acid).1 It is formed from 3-oxo lithocholic acid by gut microbiota.1 Alloisolithocholic acid (20 µM) increases the association of the nuclear hormone receptor nerve growth factor IB (Nr4a1) to the gene encoding forkhead box protein P3 (Foxp3) in isolated mouse CD4+ T cells. It induces the differentiation of isolated mouse T cells into regulatory T cells (Tregs) and the production of mitochondrial reactive oxygen species (ROS) in isolated mouse CD4+ T cells when used at a concentration of 20 µM.2 Alloisolithocholic acid (6 mg/kg) reduces hepatic bile flow and bile salt, cholesterol, and phospholipid secretion, as well as induces loss of microvilli and dilation of canaliculi in hepatocytes, markers of cholestasis, in rats.3 Fecal levels of alloisolithocholic acid are reduced in patients with Crohn’s disease or ulcerative colitis.1

This information has been provided by Cayman Chemical

References

String Representations

InChiKey (Click to copy)
SMEROWZSTRWXGI-XBESLWPFSA-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

HMDB ID
CHEBI ID
LIPIDBANK ID
BBA0006
PubChem CID
Cayman 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
16th Mar 2022