General Information of MET (ID: META00274)
Name 5-Beta-Coprostanol
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(3beta,5beta)-Cholestan-3-ol; 3b-Hydroxy-5b-cholestanol; 5 alpha Cholestan 3 alpha ol; 5 alpha Cholestan 3 beta ol; 5 alpha-Cholestan-3 alpha-ol; 5 alpha-Cholestan-3 beta-ol; 5 beta Cholestan 3 beta ol; 5 beta-Cholestan-3 alpha-ol; 5 beta-Cholestan-3 beta-ol; 5beta Coprostanol; 5beta-Cholestan-3beta-ol; Cholestan 3 ol; Cholestan-3-ol; Cholestanol; Cholestanol, (3alpha, 5beta)-isomer; Coprostanol; Coprosterol; Dihydrocholesterol; Stercorin; beta Cholestanol; beta-Cholestan-3 beta-ol, 5; beta-Cholestanol; beta-Ol, 5 beta-cholestan-3
Source Endogenous;Sterol lipids;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
221122
HMDB ID
HMDB0000577
Formula
C27H48O
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
89519
FooDB ID
FDB022125
ChemSpider ID
191826
METLIN ID
5559
Physicochemical Properties Molecular Weight 388.7 Topological Polar Surface Area 20.2
XlogP 9.4 Complexity 540
Heavy Atom Count 28 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Function
Coprosterol or coprostanol is a cholesterol derivative found in human feces, gallstones, eggs, and other biological matter. Coprosterol is the odorous principle of feces. It is formed from the biohydrogenation of cholesterol (cholest-5en-3&#946;-ol) in the gut of most higher animals and birds. This compound has frequently been used as a biomarker for the presence of human faecal matter in the environment. American physician Austin Flint named it stercorin. The transformation of cholesterol into coprosterol in its passage through the body involves a reduction of the C5:C6 double bond, and a transition from the allocholanic- to the cholanic-ring system. Although it is established that the bacterial flora of the intestine is concerned in the reduction process, the mechanism by which the stereochemical change is brought about is unknown. Current data suggests that cholestenone and coprostanone, and not cholesterol itself, are the immediate precursors of coprosterol which is formed from them in the intestine by bacterial reduction. Coprosterol is also a microbial metabolite, it can be produced by Lactobacillus.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transferases (EC 2)
            Deacetylase sirtuin-5 (SIRT5) 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 Knockout of Sirt5
                      Induced Change 5-Beta-Coprostanol concentration: decrease (FC = 0.687)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Sirt5 leads to the decrease of 5-beta-Coprostanol levels compared with control group.
References
1 Metabolomics Based Identification of SIRT5 and Protein Kinase C Epsilon Regulated Pathways in Brain. Front Neurosci. 2018 Jan 30;12:32.

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