Details of Metabolite

General Information of MET (ID: META00360)
Name Dehydroepiandrosterone sulfate
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(3-b)-3-(Sulfooxy)androst-5-en-17-one; (3-b)-3-(Sulphooxy)androst-5-en-17-one; (3-beta)-3-(Sulfooxy)androst-5-en-17-one; (3beta)-3-(Sulfooxy)-androst-5-en-17-one; 17-Ketoandrost-5-en-3b-yl sulfate; 17-Ketoandrost-5-en-3b-yl sulfuric acid; 17-Ketoandrost-5-en-3b-yl sulphate; 17-Ketoandrost-5-en-3b-yl sulphuric acid; 17-Ketoandrost-5-en-3beta-yl sulfate; 17-Ketoandrost-5-en-3beta-yl sulfuric acid; 17-Ketoandrost-5-en-3beta-yl sulphate; 17-Oxoandrost-5-en-3-yl hydrogen sulfate; 17-Oxoandrost-5-en-3-yl hydrogen sulphate; 17-Oxoandrost-5-en-3b-yl hydrogen sulfate; 17-Oxoandrost-5-en-3b-yl hydrogen sulfuric acid; 17-Oxoandrost-5-en-3b-yl hydrogen sulphate; 17-Oxoandrost-5-en-3b-yl hydrogen sulphuric acid; 17-Oxoandrost-5-en-3beta-yl hydrogen sulfate; 17-Oxoandrost-5-en-3beta-yl hydrogen sulfuric acid; 17-Oxoandrost-5-en-3beta-yl hydrogen sulphate; 3-O-Sulfodehydroepiandrosterone; 3-O-Sulphodehydroepiandrosterone; 3-b-Hydroxyandrost-5-en-17-one 3-sulfate; 3-b-Hydroxyandrost-5-en-17-one 3-sulphate; 3-beta-Hydroxyandrost-5-en-17-one 3-sulfate; 3-beta-Hydroxyandrost-5-en-17-one 3-sulphate; 3b-Hydroxy-androst-5-en-17-one hydrogen sulfate; 3b-Hydroxy-androst-5-en-17-one hydrogen sulphate; 3b-Hydroxyandrost-5-en-17-one 3-sulfate; 3b-Hydroxyandrost-5-en-17-one 3-sulfuric acid; 3b-Hydroxyandrost-5-en-17-one 3-sulphate; 3b-Hydroxyandrost-5-en-17-one 3-sulphuric acid; 3beta-Hydroxy-androst-5-en-17-one hydrogen sulfate; 3beta-Hydroxy-androst-5-en-17-one hydrogen sulphate; 3beta-Hydroxyandrost-5-en-17-one 3-sulfate; 3beta-Hydroxyandrost-5-en-17-one 3-sulfuric acid; 3beta-Hydroxyandrost-5-en-17-one 3-sulphate; Androst-5-en-17-on-3b-yl sulfate; Androst-5-en-17-on-3b-yl sulfuric acid; Androst-5-en-17-on-3b-yl sulphate; Androst-5-en-17-on-3b-yl sulphuric acid; Androst-5-en-17-on-3beta-yl sulfate; Androst-5-en-17-on-3beta-yl sulfuric acid; Androst-5-en-17-on-3beta-yl sulphate; DHA sulfate; DHEA sulfate; DHEA sulfuric acid; DHEA sulphate; DHEA sulphuric acid; DHEA-S; DHEAS; Dehydroepiandrosterone 3-sulfate; Dehydroepiandrosterone 3-sulfuric acid; Dehydroepiandrosterone 3-sulphate; Dehydroepiandrosterone 3-sulphuric acid; Dehydroepiandrosterone monosulfate; Dehydroepiandrosterone monosulfuric acid; Dehydroepiandrosterone monosulphate; Dehydroepiandrosterone monosulphuric acid; Dehydroepiandrosterone sulfuric acid; Dehydroepiandrosterone sulphate; Dehydroepiandrosterone sulphuric acid; Dehydroepiandrosterone-3-sulfate; Dehydroepiandrosterone-3-sulphate; Dehydroisoandrosterone sulfate; Dehydroisoandrosterone sulfuric acid; Dehydroisoandrosterone sulphate; Dehydroisoandrosterone sulphuric acid; Dehydroisoandrosterone-3-sulfate; Dehydroisoandrosterone-3-sulfuric acid; Dehydroisoandrosterone-3-sulphate; Dehydroisoandrosterone-3-sulphuric acid; Formylisoglutamic acid; Prasterone sulfate; Prasterone sulfuric acid; Prasterone sulphate; Prasterone sulphuric acid; Prasterone-3-sulfate; Prasterone-3-sulphate; Sulfate, dehydroepiandrosterone; Sulfate, dehydroisoandrosterone; Sulfate, dha; Sulfate, dhea; Sulfate, prasterone
Source Endogenous;Sterol lipids;Food;Carcinogenic Potency;Drug;Toxins/Pollutant
Structure Type   Sulfated steroids  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Steroids and steroid derivatives
Sulfated steroids
PubChem CID
12594
HMDB ID
HMDB0001032
Formula
C19H28O5S
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
C04555
DrugBank ID
DB05804
ChEBI ID
16814
FooDB ID
FDB022381
ChemSpider ID
12074
METLIN ID
4095
Physicochemical Properties Molecular Weight 368.5 Topological Polar Surface Area 89
XlogP 2.8 Complexity 721
Heavy Atom Count 25 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Function
Dehydroepiandrosterone sulfate or DHEA-S is the sulfated form of dehydroepiandrosterone (DHEA). This sulfation is reversibly catalyzed by sulfotransferase 2A1 (SULT2A1) primarily in the adrenals, the liver, and small intestine. In the blood, most DHEA is found as DHEA-S with levels that are about 300 times higher than those of free DHEA. Orally-ingested DHEA is converted into its sulfate when passing through the intestines and liver. Whereas DHEA levels naturally reach their peak in the early morning hours, DHEAS levels show no diurnal variation. From a practical point of view, measurement of DHEA-S is preferable to DHEA since levels are more stable. DHEA (from which DHEA-S comes from) is a natural steroid prohormone produced from cholesterol by the adrenal glands, the gonads, adipose tissue, brain, and in the skin (by an autocrine mechanism). DHEA is the precursor of androstenedione, which can undergo further conversion to produce the androgen testosterone and the estrogens estrone and estradiol. DHEA is also a potent sigma-1 agonist. Serum dehydroepiandrosterone sulfate is a classic marker for adrenarche, and subsequently for the individual hormonal milieu. Dehydroepiandrosterone sulfate is an endogenously produced sex steroid that has been hypothesized to have anti-aging effects. It also has been inversely associated with the development of atherosclerosis.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      Transient receptor (TRP-CC)
            Long transient receptor potential 4 (TRPM4) 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 Dehydroepiandrosterone sulfate addition (1h)
                      Induced Change TRPM3 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Diabetes mellitus [ICD-11: 5A14]
                      Details It is reported that dehydroepiandrosterone sulfate addition causes the increase of TRPM3 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Apolipoprotein (Apo)
            Apolipoprotein A-II (APOA2) 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 Mutation (-265T >C(rs5082)) of APOA2
                      Induced Change Dehydroepiandrosterone sulfate concentration: increase (FC = 1.57)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that mutation (-265T >C(rs5082)) of APOA2 leads to the increase of dehydroepiandrosterone sulfate levels compared with control group.
      ATP-binding cassette transporter (ABCT)
            Multidrug resistance-associated 8 (MRP8) 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 [3]
                      Introduced Variation Mutation (T546M) of ABCC11
                      Induced Change Dehydroepiandrosterone sulfate concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that mutation (T546M) of ABCC11 leads to the decrease of dehydroepiandrosterone sulfate levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Overexpression of ABCC11
                      Induced Change Dehydroepiandrosterone sulfate concentration: increase (FC = 3)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of ABCC11 leads to the increase of dehydroepiandrosterone sulfate levels compared with control group.
References
1 Transient receptor potential M3 channels are ionotropic steroid receptors in pancreatic beta cells. Nat Cell Biol. 2008 Dec;10(12):1421-30.
2 Epigenomics and metabolomics reveal the mechanism of the APOA2-saturated fat intake interaction affecting obesity. Am J Clin Nutr. 2018 Jul 1;108(1):188-200.
3 Functional characterization of common protein variants in the efflux transporter ABCC11 and identification of T546M as functionally damaging variant. Pharmacogenomics J. 2016 Apr;16(2):193-201.

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