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3-beta-Hydroxyandrost-5-en-17-one 3-sulfate

HCID 20057076
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Basic information

CAS
129509-11-1
Standard SMILES
C[C@]12CC[C@H](OS(=O)(=O)[O-])CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
InChIKey
CZWCKYRVOZZJNM-USOAJAOKSA-M
Molecular formula
C19H27O5S-
Average molar mass
367.5 g/mol
Monoisotopic mass
367.15792013

Overview

Dehydroepiandrosterone sulfate(1-) is the conjugate base of 3beta-hydroxyandrost-5-en-17-one 3-sulfate arising from deprotonation of the sulfate OH group; major species at pH 7.3. It has a role as a human metabolite. It is a conjugate base of a dehydroepiandrosterone sulfate.

Names & identifiers

Preferred name
3-beta-Hydroxyandrost-5-en-17-one 3-sulfate
IUPAC
[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] sulfate

Names & synonyms

3-beta-hydroxyandrost-5-en-17-one 3-sulfateRefChem:1067400[3H]dehydroepiandrosterone sulfateCCG-20447317-oxoandrost-5-en-3beta-yl sulfate[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] sulfate[3H]dehydroepiandrosterone sulphate[3H]DHEASGTPL4528GTPL5577CHEBI:57905dehydroepiandrosterone sulfate(1-)
Show more names
DTXSID4012266073beta-sulfooxy-androst-5-en-17-oneNCGC00162137-02129509-11-1PD0483213beta-hydroxyandrost-5-en-17-one 3-sulfate anion3beta-hydroxyandrost-5-en-17-one 3-sulfate(1-)Q27077014

Database identifiers

CAS
129509-11-1
PubChem CID
20057076
DTXSID
DTXSID401226607
ChEBI
CHEBI:57905

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
91.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
1
Heavy atoms
25
Formal charge
-1
Complexity
707

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety & protection

Minimum Risk LevelDehydroepiandrosterone sulfate levels above 1890 micromol/L or 700-800 µg/dL are highly suggestive of adrenal dysfunction.

Toxicology

Health Effects · 1 item

Some researchers believe DHEAS supplements might actually raise the risk of breast cancer, prostate cancer, heart disease, diabetes and stroke. DHEAS may stimulate tumor growth in types of cancer that are sensitive to hormones, such as some types of breast, uterine, and prostate cancer. DHEAS may increase prostate swelling in men with benign prostatic hyperplasia (BPH), an enlarged prostate gland. High doses of DHEAS may cause aggressiveness, irritability, trouble sleeping, and the growth of body or facial hair on women. It also may stop menstruation and lower the levels of HDL ('good' cholesterol), which could raise the risk of heart disease. Other reported side effects include acne, heart rhythm problems, liver problems, hair loss (from the scalp), and oily skin. In women, DHEA may cause decreased breast size, a deep voice, increased genital size, irregular periods, oily skin, and unnatural hair growth. In men, DHEAS may cause aggression, breast tenderness or enlargement, decreased testes size, and urinary urgency. DHEAS may interfere with the way the body processes certain agents using the liver's cytochrome P450 enzyme system. Chronically high levels of Dehydroepiandrosterone sulfate are associated with male pseudohermaphrodism with gynecomastia.

Exposure RoutesEndogenous, ingestion
Toxicity Summary · 1 item

Although it predominantly functions as an endogenous precursor to more potent androgens such as testosterone and dihydroxytestosterone, DHEA (which is produced from DHEAS) has been found to possess some degree of androgenic activity in its own right, acting as a low affinity (Ki = 1 μM), weak partial agonist of the androgen receptor. DHEA has also been found to bind to and activate the ERα and ERβ estrogen receptors with Ki values of 1.1 μM and 0.5 μM, respectively. When taken in sufficient quantities DHEAS can cause masculinizing effects. DHEAS is considered an androgenic steroid precursor because testosterone (its product) is an androgen or male hormone. In males and females, conversion of DHEAS to testosterone requires the enzyme 17β-hydroxysteroid dehydrogenase. Testosterone plays a key role in the development of male reproductive tissues such as the testis and prostate as well as promoting secondary sexual characteristics such as increased muscle, bone mass, and the growth of body hair. High levels of testosterone can lead to masculinization in females or premature puberty in young boys. Chronically high levels in adults increase the incidence of heart attack, stroke and blood clots by lowering the level of HDL (good cholesterol). The development of breast tissue in males, a condition called gynecomastia (which is usually caused by high levels of circulating estradiol), arises because of increased conversion of testosterone to estradiol by the enzyme aromatase. Reduced sexual function and temporary infertility can also occur in males.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Dehydroepiandrosterone sulfate (DHEAS) is the sulfate ester of DHEA. This conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestine. DHEA sulfate can also be back-converted to DHEA through the action of steroid sulfatase. In the blood, most DHEA is found as DHEAS with levels that are about 300 times higher than those of free DHEA. Orally ingested DHEA is converted to its sulfate when passing through intestines and liver. DHEAS levels show no diurnal variation. In males and females, conversion of DHEAS to DHEA and then to testosterone requires the enzyme 17β-hydroxysteroid dehydrogenase.

Uses & manufacturing

UsesInvestigated for use/treatment in asthma and burns and burn infections.

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Compound notes

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Signs and Symptoms · 1 item

In women, DHEAS may cause decreased breast size, a deep voice, increased genital size, irregular periods, oily skin, and unnatural hair growth. In men, DHEAS may cause aggression, breast tenderness or enlargement, decreased testes size, and urinary urgency.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).