Details of Metabolite

General Information of MET (ID: META00717)
Name Dihydroartemisinin
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-[methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amino]oxane-2-carboxylate
Source Endogenous
Structure Type   Carbohydrates and carbohydrate conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic oxygen compounds
Organooxygen compounds
Carbohydrates and carbohydrate conjugates
PubChem CID
71316864
HMDB ID
HMDB0061088
Formula
C15H24O5
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
Physicochemical Properties Molecular Weight 485.4 Topological Polar Surface Area 120
XlogP 0.5 Complexity 653
Heavy Atom Count 34 Rotatable Bond Count 8
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 11
Function
Dihydroartemisinin (DHA) is a metabolite of artemether. Artemether is an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria. It is combined with Lumefantrine and sold by Novartis under the brand names Riamet and Co-Artem.
Regulatory Network
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 [1]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Dihydroartemisinin concentration: increase (FC = 1.45 / 1.82)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of dihydroartemisinin levels compared with control group.
      Sugar transporter (ST)
            Glucose transporter type 2 (GLUT-2) 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 Overexpression of SLC2A2
                      Induced Change Dihydroartemisinin concentration: increase (FC = 5 - 10)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC2A2 leads to the increase of dihydroartemisinin levels compared with control group.
            Glucose transporter type 8 (GLUT-8) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Mutation (di-leucine to di-alanine substitution (LL-AA)) of Slc2a8
                      Induced Change Dihydroartemisinin concentration: increase (FC = 5 - 10)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that mutation (di-leucine to di-alanine substitution (LL-AA)) of Slc2a8 leads to the increase of dihydroartemisinin levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Overexpression of Slc2a8
                      Induced Change Dihydroartemisinin concentration: increase (FC = 5 - 10)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of Slc2a8 leads to the increase of dihydroartemisinin levels compared with control group.
            HepG2 glucose transporter (SLC2A1) 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 Overexpression of SLC2A1
                      Induced Change Dihydroartemisinin concentration: increase (FC = 100)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC2A1 leads to the increase of dihydroartemisinin levels compared with control group.
References
1 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
2 Intestinal dehydroascorbic acid (DHA) transport mediated by the facilitative sugar transporters, GLUT2 and GLUT8. J Biol Chem. 2013 Mar 29;288(13):9092-101.

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