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
3D model of Alloisolithocholic Acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
Admin
Created at
-
Updated at
16th Mar 2022