Details of Metabolite

General Information of MET (ID: META00013)
Name 7-Alpha,27-Dihydroxycholesterol
Synonyms   Click to Show/Hide Synonyms of This Metabolite
5-Cholestene-3beta,7alpha,26-triol; 7-alpha,27-Dihydroxycholesterol; 7alpha,26-Dihydroxycholesterol; 7alpha,27-Dihydroxycholesterol; Cholest-5-ene-3,7,27-triol; Cholest-5-ene-3- b,7-a,27-triol; Cholest-5-ene-3-b,7-a,27-triol; Cholest-5-ene-3-beta,7-alpha,27-triol; Cholest-5-ene-3beta,7alpha,26-triol; Cholest-5-ene-3beta,7alpha,27-triol
Source Endogenous;Sterol lipids;Food
Structure Type   Bile acids, alcohols and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Steroids and steroid derivatives
Bile acids, alcohols and derivatives
PubChem CID
440985
HMDB ID
HMDB0006281
Formula
C27H46O3
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
C06341
ChEBI ID
18431
FooDB ID
FDB023875
ChemSpider ID
389810
Physicochemical Properties Molecular Weight 418.7 Topological Polar Surface Area 60.7
XlogP 6 Complexity 644
Heavy Atom Count 30 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Function
7-a,27-dihydroxycholesterol is an intermediate in bile acid biosynthesis. The enzyme 27-Hydroxycholesterol 7alpha-monooxygenase [EC:1.14.13.60] catalyzes the production of this metabolite from 27-hydroxycholesterol. This enzyme reaction is irreversible and occurs in the endoplasmic reticulum.
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,27-Dihydroxycholesterol 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,27-dihydroxycholesterol addition causes the increase of GPR183 protein activity compared with control group.
References
1 Oxysterols direct B-cell migration through EBI2. Nature. 2011 Jul 27;475(7357):519-23.

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