Structure Database (LMSD)

Common Name
Dehydroepiandrosterone
Systematic Name
3β-hydroxyandrost-5-en-17-one
Synonyms
LM ID
LMST02020021
Formula
C19H28O2
Exact Mass
Calculate m/z
288.20893
Sum Composition
ST 19:2;O2
Status
Curated
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Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C19 steroids (androgens) and derivatives [ST0202]

Biological Context

Dehydroepiandrosterone (DHEA) is an endogenous steroid hormone that is secreted primarily by the adrenal gland and is the most abundant sex steroid.1,2,3 Metabolites of DHEA include androstenedione , which subsequently may be metabolized to testosterone (ISO60154 | 15645) or estrone which is an estradiol (ISO60155 | 10006315) precursor.1,2,3 In addition to serving as an intermediate in the biosynthesis of sex steroids, DHEA directly modulates a number of cellular and nuclear receptors.1,2,3

This information has been provided by Cayman Chemical

References

1. Kim, C., and Halter, J.B. Endogenous sex hormones, metabolic syndrome, and diabetes in men and women. Curr. Cardiol. Rep. 16(4), 467 (2014).
2. Mannic, T., Viguie, J., and Rossier, M.F. In vivo and in vitro evidences of dehydroepiandrosterone protective role on the cardiovascular system. Int. J. Endocrinol. Metab. 13(2), e24660 (2015).
3. Samaras, N., Papadopoulou, M.A., Samaras, D., et al. Off-label use of hormones as an antiaging strategy: A review. Clin. Interv. Aging 9, 1175-1186 (2014).

String Representations

InChiKey (Click to copy)
FMGSKLZLMKYGDP-USOAJAOKSA-N
InChi (Click to copy)
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)C(=O)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1

Other Databases

Wikipedia
Dehydroepiandrosterone
KEGG ID
C01227
HMDB ID
HMDB0000077
CHEBI ID
28689
LIPIDBANK ID
SST0185
PubChem CID
5881
SwissLipids ID
SLM:000390142
Cayman ID
15728
PDB ID
AND
GuidePharm ID
2370

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 4
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 300.12
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 4.17
Molar Refractivity 83.23

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Updated at
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