Details of Metabolite

General Information of MET (ID: META00959)
Name 24,25-Epoxy-cholesterol
Synonyms   Click to Show/Hide Synonyms of This Metabolite
24(S),25-Epoxycholesterol; 24,25-epoxy-cholesterol; 24(S), 25-epoxycholesterol; 77058-74-3; 24S,25-epoxy-cholesterol; 24S,25-epoxy-cholest-5-en-3beta-ol; CHEMBL434302; CHEBI:41633; (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2S)-3,3-dimethyloxiran-2-yl]butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; Spectrum5_001979; 24,25(S)-EPOXYCHOLESTEROL; 24S,25-EpoxyC; lopenta[a]phenanthren-3-ol; (24S)-25-epoxycholesterol
Source Endogenous;Yeast Metabolite;Sterol lipids;Food;Toxins/Pollutant;Cosmetic;TCM Ingredients;Microbial
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
3247059
Formula
C27H44O2
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=3247059"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
Physicochemical Properties Molecular Weight 400.6 Topological Polar Surface Area 32.8
XlogP 6.6 Complexity 680
Heavy Atom Count 29 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      ATP-binding cassette transporter (ABCT)
            ATP-binding cassette A1 (ABCA1) 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 24,25-Epoxy-cholesterol addition (24 hours)
                      Induced Change ABCA1 mRNA levels: increase (FC = 22.9)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lipid metabolism disorders [ICD-11: 5C52]
                      Details It is reported that 24,25-epoxy-cholesterol addition causes the increase of ABCA1 mRNA levels compared with control group.
      Nuclear hormone receptor (NHR)
            Nuclear receptor subfamily 4 group A member 2 (NR4A2B) 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 24,25-Epoxy-cholesterol addition (3 hours)
                      Induced Change NR4A2B mRNA levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Atherosclerosis [ICD-11: BD40]
                      Details It is reported that 24,25-epoxy-cholesterol addition causes the increase of NR4A2B mRNA levels compared with control group.
            Oxysterols receptor LXR-alpha (NR1H3) 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 24,25-Epoxy-cholesterol addition (3 hours)
                      Induced Change NR1H3 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Atherosclerosis [ICD-11: BD40]
                      Details It is reported that 24,25-epoxy-cholesterol addition causes the increase of NR1H3 protein activity compared with control group.
      Oxidoreductases (EC 1)
            Tyrosine 3-monooxygenase (TH) 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 24,25-Epoxy-cholesterol addition (3 hours)
                      Induced Change TH mRNA levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Atherosclerosis [ICD-11: BD40]
                      Details It is reported that 24,25-epoxy-cholesterol addition causes the increase of TH mRNA levels compared with control group.
      Sodium:neurotransmitter symporter (SNF)
            Dopamine transporter (DAT) 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 24,25-Epoxy-cholesterol addition (1 hours)
                      Induced Change SLC6A3 mRNA levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Atherosclerosis [ICD-11: BD40]
                      Details It is reported that 24,25-epoxy-cholesterol addition causes the increase of SLC6A3 mRNA levels compared with control group.
References
1 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem. 2001 Oct 19;276(42):38378-87.
2 Brain endogenous liver X receptor ligands selectively promote midbrain neurogenesis. Nat Chem Biol. 2013 Feb;9(2):126-33.

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