Structure Database (LMSD)
Common Name
7alpha,25-dihydroxycholesterol
Systematic Name
cholest-5-en-3β,7α,25-triol
Synonyms
LM ID
LMST04030166
Formula
Exact Mass
Calculate m/z
418.344695
Sum Composition
Status
Curated
3D model of 7alpha,25-dihydroxycholesterol
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
GPR183 (also known as Epstein-Barr virus-induced gene 2) is an orphan G protein-coupled receptor (GPCR) that is highly expressed in spleen and is required for humoral immune responses, including B cell migration and T cell-dependent antibody production.1,2 7α,25-dihydroxy Cholesterol (7α,25-DHC) is a potent agonist of GPR183 that induces specific activation of the receptor with an EC50 value of 50 nM (Kd = 450 pM).1,2 At concentrations below 3 μM, it does not show any appreciable binding activity when tested against eight different nuclear hormone receptors including LXR and thirty-one different G protein-coupled receptors in a panel of reporter gene assays.2 7α,25-DHC can act as a potent chemokine, affecting migration of immune cells expressing GPR183 both in vitro (EC50 = 500 pM) and in vivo.1,2
This information has been provided by Cayman Chemical
References
2. Liu, C., Yang, X.V., Wu, J., et al. Oxysterols direct B-cell migration through EB12. Nature 475(7357), 519-523 (2011).
Reactions
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References
String Representations
InChiKey (Click to copy)
BQMSKLCEWBSPPY-IKVTXIKFSA-N
InChi (Click to copy)
InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1
SMILES (Click to copy)
[C@@]12([H])[C@H](O)C=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(O)(C)C)CC[C@@]21[H]
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
30
Rings
4
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
449.95
Topological Polar Surface Area
60.69
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
3
logP
6.33
Molar Refractivity
123.44
Admin
Created at
-
Updated at
3rd Feb 2021