ContaminantDB: Dehydroepiandrosterone sulfate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:00:38 UTC

Update Date

2026-05-14 18:16:20 UTC

Accession Number

CHEM003202

Identification

Common Name

Dehydroepiandrosterone sulfate

Class

Small Molecule

Description

Dehydroepiandrosterone sulfate or DHEAS is the sulfated form of dehydroepiandrosterone (DHEA). This sulfation is reversibly catalyzed by sulfotransferase 2A1 (SULT2A1) primarily in the adrenals, the liver, and small intestine. 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. Whereas DHEA levels naturally reach their peak in the early morning hours, DHEAS levels show no diurnal variation. From a practical point of view, measurement of DHEAS is preferable to DHEA, as levels are more stable. DHEA (from which DHEAS comes from) is a natural steroid prohormone produced from cholesterol by the adrenal glands, the gonads, adipose tissue, brain and in the skin (by an autocrine mechanism). DHEA is the precursor of androstenedione, which can undergo further conversion to produce the androgen testosterone and the estrogens estrone and estradiol. DHEA is also a potent sigma-1 agonist. DHEAS can serve as a precursor for testosterone; androstenedione; estradiol; and estrone. Serum dehydroepiandrosterone sulfate is a classic marker for adrenarche and, subsequently, for the individual hormonal milieu Dehydroepiandrosterone sulfate is an endogenously produced sex steroid that has been hypothesized to have anti aging effects It also has been inversely associated with development of atherosclerosis (1, 2, 3). DHEA-S is the principal adrenal androgen and is secreted together with cortisol under the control of ACTH and prolactin. DHEA-S is elevated with hyperprolactinemia.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Animal Toxin
Ester
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3-beta)-3-(Sulfooxy)androst-5-en-17-one	ChEBI
17-Ketoandrost-5-en-3beta-yl sulfate	ChEBI
17-Oxoandrost-5-en-3beta-yl hydrogen sulphate	ChEBI
3-O-Sulfodehydroepiandrosterone	ChEBI
3beta-Hydroxyandrost-5-en-17-one 3-sulfate	ChEBI
Androst-5-en-17-on-3beta-yl sulfuric acid	ChEBI
Dehydroepiandrosterone 3-sulfate	ChEBI
Dehydroepiandrosterone monosulfate	ChEBI
Dehydroepiandrosterone sulphate	ChEBI
Dehydroisoandrosterone sulfate	ChEBI
Dehydroisoandrosterone-3-sulfate	ChEBI
DHEA sulfate	ChEBI
DHEA-S	ChEBI
DHEAS	ChEBI
Prasterone sulfate	ChEBI
(3-b)-3-(Sulfooxy)androst-5-en-17-one	Generator
(3-b)-3-(Sulphooxy)androst-5-en-17-one	Generator
(3-beta)-3-(Sulphooxy)androst-5-en-17-one	Generator
(3-Β)-3-(sulfooxy)androst-5-en-17-one	Generator
(3-Β)-3-(sulphooxy)androst-5-en-17-one	Generator
17-Ketoandrost-5-en-3b-yl sulfate	Generator
17-Ketoandrost-5-en-3b-yl sulfuric acid	Generator
17-Ketoandrost-5-en-3b-yl sulphate	Generator
17-Ketoandrost-5-en-3b-yl sulphuric acid	Generator
17-Ketoandrost-5-en-3beta-yl sulfuric acid	Generator
17-Ketoandrost-5-en-3beta-yl sulphate	Generator
17-Ketoandrost-5-en-3beta-yl sulphuric acid	Generator
17-Ketoandrost-5-en-3β-yl sulfate	Generator
17-Ketoandrost-5-en-3β-yl sulfuric acid	Generator
17-Ketoandrost-5-en-3β-yl sulphate	Generator
17-Ketoandrost-5-en-3β-yl sulphuric acid	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulfate	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulfuric acid	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulphate	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulphuric acid	Generator
17-Oxoandrost-5-en-3beta-yl hydrogen sulfate	Generator
17-Oxoandrost-5-en-3beta-yl hydrogen sulfuric acid	Generator
17-Oxoandrost-5-en-3beta-yl hydrogen sulphuric acid	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulfate	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulfuric acid	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulphate	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulphuric acid	Generator
3-O-Sulphodehydroepiandrosterone	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulfate	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulfuric acid	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulphate	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulphuric acid	Generator
3beta-Hydroxyandrost-5-en-17-one 3-sulfuric acid	Generator
3beta-Hydroxyandrost-5-en-17-one 3-sulphate	Generator
3beta-Hydroxyandrost-5-en-17-one 3-sulphuric acid	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulfate	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulfuric acid	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulphate	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulphuric acid	Generator
Androst-5-en-17-on-3b-yl sulfate	Generator
Androst-5-en-17-on-3b-yl sulfuric acid	Generator
Androst-5-en-17-on-3b-yl sulphate	Generator
Androst-5-en-17-on-3b-yl sulphuric acid	Generator
Androst-5-en-17-on-3beta-yl sulfate	Generator
Androst-5-en-17-on-3beta-yl sulphate	Generator
Androst-5-en-17-on-3beta-yl sulphuric acid	Generator
Androst-5-en-17-on-3β-yl sulfate	Generator
Androst-5-en-17-on-3β-yl sulfuric acid	Generator
Androst-5-en-17-on-3β-yl sulphate	Generator
Androst-5-en-17-on-3β-yl sulphuric acid	Generator
Dehydroepiandrosterone 3-sulfuric acid	Generator
Dehydroepiandrosterone 3-sulphate	Generator
Dehydroepiandrosterone 3-sulphuric acid	Generator
Dehydroepiandrosterone monosulfuric acid	Generator
Dehydroepiandrosterone monosulphate	Generator
Dehydroepiandrosterone monosulphuric acid	Generator
Dehydroepiandrosterone sulfuric acid	Generator
Dehydroepiandrosterone sulphuric acid	Generator
Dehydroisoandrosterone sulfuric acid	Generator
Dehydroisoandrosterone sulphate	Generator
Dehydroisoandrosterone sulphuric acid	Generator
Dehydroisoandrosterone-3-sulfuric acid	Generator
Dehydroisoandrosterone-3-sulphate	Generator
Dehydroisoandrosterone-3-sulphuric acid	Generator
DHEA sulfuric acid	Generator
DHEA sulphate	Generator
DHEA sulphuric acid	Generator
Prasterone sulfuric acid	Generator
Prasterone sulphate	Generator
Prasterone sulphuric acid	Generator
(3beta)-3-(Sulfooxy)-androst-5-en-17-one	HMDB
17-Oxoandrost-5-en-3-yl hydrogen sulfate	HMDB
17-Oxoandrost-5-en-3-yl hydrogen sulphate	HMDB
3-b-Hydroxyandrost-5-en-17-one 3-sulfate	HMDB
3-b-Hydroxyandrost-5-en-17-one 3-sulphate	HMDB
3-beta-Hydroxyandrost-5-en-17-one 3-sulfate	HMDB
3-beta-Hydroxyandrost-5-en-17-one 3-sulphate	HMDB
3b-Hydroxy-androst-5-en-17-one hydrogen sulfate	HMDB
3b-Hydroxy-androst-5-en-17-one hydrogen sulphate	HMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulfate	HMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulphate	HMDB
Dehydroepiandrosterone-3-sulfate	HMDB
Dehydroepiandrosterone-3-sulphate	HMDB
Formylisoglutamic acid	HMDB
Prasterone-3-sulfate	HMDB
Prasterone-3-sulphate	HMDB
DHA sulfate	HMDB
Sulfate, dehydroisoandrosterone	HMDB
Sulfate, prasterone	HMDB
Sulfate, dhea	HMDB
Sulfate, dehydroepiandrosterone	HMDB
Sulfate, dha	HMDB

Chemical Formula

C₁₉H₂₈O₅S

Average Molecular Mass

368.488 g/mol

Monoisotopic Mass

368.166 g/mol

CAS Registry Number

651-48-9

IUPAC Name

[(3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-dimethyl-1-oxo-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

Traditional Name

[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O

InChI Identifier

InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1

InChI Key

CZWCKYRVOZZJNM-USOAJAOKSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Sulfated steroids

Direct Parent

Sulfated steroids

Alternative Parents

Substituents

Sulfated steroid skeleton
Androstane-skeleton
17-oxosteroid
Oxosteroid
Delta-5-steroid
Sulfuric acid ester
Alkyl sulfate
Sulfuric acid monoester
Sulfate-ester
Organic sulfuric acid or derivatives
Ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:16814 )
17-oxo steroid (CHEBI:16814 )
sulfates (C04555 )
C19 steroids (androgens) and derivatives (C04555 )
Androgens (C04555 )
Sulfates (LMST05020010 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Kidney
Liver
Prostate

Pathways

Name	SMPDB Link	KEGG Link
17-Beta Hydroxysteroid Dehydrogenase III Deficiency	SMP00356	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

EC 2.7.1.33 (pantothenate kinase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0081 g/L	ALOGPS
logP	0.49	ALOGPS
logP	3.42	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.65 m³·mol⁻¹	ChemAxon
Polarizability	39.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-0097000000-e6d4f60e9803940d2f55	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-d49a8b7164a230745f20	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-3009000000-bd7e895ed74eba8a0f23	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-8d7ea5bd8a8a0d5219c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-9001000000-5d89a4081c0f6b0c3324	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0049000000-f9a938b029283c157bdf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0091000000-c2b83d86ae8174524e1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-5792000000-20638b1484fe342eb3c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0029000000-79344bc1ba3ea2c26db7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-1092000000-3b129a6c30b2629e1661	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-008i-6090000000-35cc2726715438281170	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-c58c9c29bacda1fca240	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1009000000-d5f9b663138c7975150b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9105000000-a5c4a9d21c991c730dab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0019000000-e7315ac14210f0dc3930	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-0292000000-06a461930592bd575f19	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-4920000000-e6055497e2f92515f76a	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Endogenous, ingestion

Mechanism of Toxicity

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.

Metabolism

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.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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

Minimum Risk Level

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

Health Effects

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.

Symptoms

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.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB05804

HMDB ID

HMDB0001032

FooDB ID

FDB022381

Phenol Explorer ID