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dehydroepiandrosterone
Sign in to saveAlso known as androstenolone, DHA, DHEA, 3beta-Hydroxyandrost-5-en-17-one, Astenile, (3beta,16alpha)-3,16-dihydroxy-androst-5-en-17-one, Androsten-3beta-ol-17-one, (3beta)-3-hydroxy-Androst-5-en-17-one
Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It functions as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids both in the gonads and in various other tissues. However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors, and acting as a neurosteroid and modulator of neurotrophic factor recep
Chemical data
- Formula
- C19H28O2
- Molecular weight
- 288.4 g/mol
- IUPAC name
- (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C
- InChIKey
- FMGSKLZLMKYGDP-USOAJAOKSA-N
- XLogP
- 3.2
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
18,683 papers- Dehydroepiandrosterone: a neuroactive steroid.The Journal of steroid biochemistry and molecular biology · 2015
- Dehydroepiandrosterone metabolism.The Journal of endocrinology · 1996
- Dehydroepiandrosterone (DHEA): a fountain of youth?The Journal of clinical endocrinology and metabolism · 1996
- DHEA: dehydroepiandrosterone.American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists · 2000
- Dehydroepiandrosterone and sport.The Medical journal of Australia · 1999
via PubMed
~13 min read
Encyclopedic overview
33 sectionsContents
- Biological function
- As an androgen
- As an estrogen
- As a neurosteroid
- Biological activity
- Hormonal activity
- Androgen receptor
- Estrogen receptors
- Other nuclear receptors
- Neurosteroid activity
- Neurotransmitter receptors
- Neurotrophin receptors
- Microtubule-associated protein 2
- ADHD
- Other activity
- G6PDH inhibitor
- Cancer
- Miscellaneous
- DHEA in regards to aging
- Biochemistry
- Biosynthesis
- Increasing endogenous production
- Distribution
- Metabolism
- Pregnancy
- Levels
- Measurement
- Chemistry
- Isomers
- History
- See also
- References
- Further reading
Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It functions as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids both in the gonads and in various other tissues. However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors, and acting as a neurosteroid and modulator of neurotrophic factor receptors.
In the United States, DHEA is sold as an over-the-counter supplement, and medication called prasterone.
Excerpted from Wikipedia’s “dehydroepiandrosterone” article, available under the CC BY-SA 4.0 licence.