Details of Metabolite

General Information of MET (ID: META00439)
Name 7-Alpha-Hydroxycholesterol
Synonyms   Click to Show/Hide Synonyms of This Metabolite
7 alpha-Hydroxycholesterol; 7alpha-Hydroxy-cholesterol; 7alpha-Hydroxycholest-5-en-3beta-ol; 7alpha-Hydroxycholesterol; Cholest-5-en-3 beta,7 alpha-diol; Cholest-5-ene-3beta,7alpha-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
107722
HMDB ID
HMDB0001496
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
C03594
ChEBI ID
17500
FooDB ID
FDB022655
ChemSpider ID
96891
Physicochemical Properties Molecular Weight 402.7 Topological Polar Surface Area 40.5
XlogP 7.4 Complexity 624
Heavy Atom Count 29 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
7alpha-Hydroxycholesterol is an oxysterol and can serve as a biomarker for lipid peroxidation. Products of cholesterol oxidation accumulate within atherosclerotic plaque and have been proposed to contribute to inflammatory signalling in the diseased artery. 7alpha-Hydroxycholesterol is a cholesterol oxide that has been described as a biomarker of oxidative stress in subjects with impaired glucose tolerance and diabetes. 7alpha-Hydroxycholesterol has been identified in the human placenta.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      GPCR rhodopsin (GPCR-1)
            G-protein coupled receptor 183 (GPR183) 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 7-Alpha-Hydroxycholesterol addition (48 hours)
                      Induced Change GPR183 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Systemic inflammatory response syndrome [ICD-11: 1H0Z]
                      Details It is reported that 7-alpha-hydroxycholesterol addition causes the increase of GPR183 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) 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 [2]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change 7-Alpha-Hydroxycholesterol concentration: decrease (FC = 0.08 / 0.14)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of 7-alpha-hydroxycholesterol levels compared with control group.
References
1 Oxysterols direct B-cell migration through EBI2. Nature. 2011 Jul 27;475(7357):519-23.
2 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.

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