Details of Metabolite

General Information of MET (ID: META00004)
Name 25-Hydroxycholesterol
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(beta)-Cholest-5-ene-3-25-diol; 25-Hydroxy-cholesterol; 25-Hydroxycholest-5-en-3-ol; 5-Cholestene-3beta-25-diol; Cholest-5-en-3beta-25-diol; Cholest-5-ene-3-b,25-diol; Cholest-5-ene-3-beta,25-diol; Cholest-5-ene-3beta-25-diol
Source Endogenous;Food
Structure Type   Cholestane steroids  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Steroids and steroid derivatives
Cholestane steroids
PubChem CID
53477807
HMDB ID
HMDB0006247
Formula
C27H46O2
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C15519
ChEBI ID
37616
FooDB ID
FDB023859
METLIN ID
3899
Physicochemical Properties Molecular Weight 402.7 Topological Polar Surface Area 40.5
XlogP 6.8 Complexity 636
Heavy Atom Count 29 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
25-Hydroxycholesterol is steroid derivative that suppresses the cleavage of sterol regulatory element binding proteins (SREBPs). It also induces apoptosis through down-regulation of Bcl-2 expression and activation of caspases. 25-Hydroxycholesterol also enhances Interleukin-1 beta (IL-1beta-induced) IL-8 production. 25-hydroxycholesterol is endogenously produced from cholesterol at early time intervals after cholesterol ingestion. It inhibits HMG-CoA reductase and so it also plays a significant role in the in vivo regulation of cholesterol biosynthesis after an acute dietary cholesterol challenge.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      Nuclear hormone receptor (NHR)
            Nuclear receptor ROR-gamma (RORC) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation 25-Hydroxycholesterol addition (24h)
                      Induced Change RORC protein binding activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that 25-hydroxycholesterol addition causes the increase of RORC protein binding activity compared with control group.
References
1 Structural basis for hydroxycholesterols as natural ligands of orphan nuclear receptor RORgamma. Mol Endocrinol. 2010 May;24(5):923-9.

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