Common Name3beta-hydroxyandrost-5-en-17-one
DescriptionDehydroepiandrosterone (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.
Structure
Molecular FormulaC19H28O2
Average Mass288.42440
Monoisotopic Mass288.20893
IUPAC Name(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
Traditional Name(2r,5s,15s)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
CAS Registry Number53-43-0
SMILESC[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
InChI IdentifierInChI=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
InChI KeyFMGSKLZLMKYGDP-USOAJAOKSA-N
CHEBI IDCHEBI:28689
HMDB IDHMDB0000077
Pathways
NameSMPDB/PathBank
Androgen and Estrogen Metabolism
17-Beta Hydroxysteroid Dehydrogenase III Deficiency
Aromatase deficiency
StateNot Available
Water Solubility4.38e-02 g/l
logP3.53
logS-3.82
pKa (Strongest Acidic)18.20
pKa (Strongest Basic)-1.40
Hydrogen Acceptor Count2
Hydrogen Donor Count1
Polar Surface Area37.3 Ų
Rotatable Bond Count0
Physiological Charge0
Formal Charge0
Refractivity84.66 m³·mol⁻¹
Polarizability33.20

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