Details of Metabolite

General Information of MET (ID: META00150)
Name Dehydroepiandrosterone
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+)-Dehydroisoandrosterone; (3-beta)-3-Hydroxyandrost-5-en-17-one; (3beta)-3-Hydroxy-androst-5-en-17-one; (3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-one; 17-Chetovis; 17-Hormoforin; 3-BETA-HYDROXY-5-androsten-17-one; 3-beta-Hydroxyandrost-5-en-17-one; 3b-Hydroxy-D5-androsten-17-one; 3beta-Hydroxy-5-androsten-17-one; 3beta-Hydroxy-D5-androsten-17-one; 3beta-Hydroxy-androst-5-en-17-one; 3beta-Hydroxyandrost-5-en-17-one; 5 Androsten 3 beta hydroxy 17 one; 5 Androsten 3 ol 17 one; 5,6-Dehydroisoandrosterone; 5,6-Didehydroisoandrosterone; 5-Androsten-3-beta-hydroxy-17-one; 5-Androsten-3-beta-ol-17-one; 5-Androsten-3-ol-17-one; 5-Androsten-3b-ol-17-one; 5-Androsten-3beta-ol-17-one; 5-Dehydro-epiandrosterone; 5-Dehydroepiandrosterone; Andrestenol; Androst-5-ene-3b-ol-17-one; Androst-5-ene-3beta-ol-17-one; Androsten-3beta-ol-17-one; Androstenolone; Astenile; Biolaif; D5-Androsten-3b-ol-17-one; D5-Androsten-3beta-ol-17-one; DHA; DHEA; Deandros; Dehydro-epi-androsterone; Dehydroisoandrosterone; Diandron; Diandrone; EM-760Dehydroandrosterone; Hydroxyandrostenone; Intrarosa; Prasterona; Prasterone; Prasterone, 3 alpha isomer; Prasterone, 3 alpha-isomer; Prasteronum; Prestara; Psicosterone; trans-Dehydroandrosterone
Source Endogenous;Sterol lipids;Food;Carcinogenic Potency;Cosmetic
Structure Type   Androstane steroids  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Steroids and steroid derivatives
Androstane steroids
PubChem CID
5881
HMDB ID
HMDB0000077
Formula
C19H28O2
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
C01227
DrugBank ID
DB01708
ChEBI ID
28689
FooDB ID
FDB021808
ChemSpider ID
8036443
METLIN ID
5133
Physicochemical Properties Molecular Weight 288.4 Topological Polar Surface Area 37.3
XlogP 3.2 Complexity 508
Heavy Atom Count 21 Rotatable Bond Count N.A.
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue, and the brain. DHEA is structurally similar to and is a precursor of, androstenedione, testosterone, estradiol, estrone, and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate or DHEA-S) before secretion. DHEA-S is the sulfated version of DHEA; this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEA-S with levels that are about 300 times higher than free DHEA. Blood measurements of DHEA-S/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEA-S.
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 addition (48 hours)
                      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 addition causes the increase of TRPM3 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      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 [2]
                      Introduced Variation Inhibition (4,4'-Diisothiocyano-2,2'-stilbenedisulfonic acid) of ABCC11
                      Induced Change Dehydroepiandrosterone concentration: decrease (FC = 0.10)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that inhibition of ABCC11 leads to the decrease of dehydroepiandrosterone levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Mutation (G180R) of ABCC11
                      Induced Change Dehydroepiandrosterone concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that mutation (G180R) of ABCC11 leads to the decrease of dehydroepiandrosterone 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 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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