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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:43 UTC
HMDB IDHMDB01032
Secondary Accession NumbersNone
Metabolite Identification
Common NameDehydroepiandrosterone sulfate
DescriptionDehydroepiandrosterone 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 (PMID 10599744 ). Dehydroepiandrosterone sulfate is an endogenously produced sex steroid that has been hypothesized to have anti aging effects (PMID 16960027 ). It also has been inversely associated with development of atherosclerosis (PMID 8956025 ).
Structure
Thumb
Synonyms
ValueSource
(3-beta)-3-(Sulfooxy)androst-5-en-17-oneChEBI
17-Ketoandrost-5-en-3beta-yl sulfateChEBI
17-Oxoandrost-5-en-3beta-yl hydrogen sulphateChEBI
3-O-SulfodehydroepiandrosteroneChEBI
3beta-Hydroxyandrost-5-en-17-one 3-sulfateChEBI
Androst-5-en-17-on-3beta-yl sulfuric acidChEBI
Dehydroepiandrosterone 3-sulfateChEBI
Dehydroepiandrosterone monosulfateChEBI
Dehydroepiandrosterone sulphateChEBI
Dehydroisoandrosterone sulfateChEBI
Dehydroisoandrosterone-3-sulfateChEBI
DHEA sulfateChEBI
DHEA-SChEBI
DHEASChEBI
Prasterone sulfateChEBI
(3-b)-3-(Sulfooxy)androst-5-en-17-oneGenerator
(3-b)-3-(Sulphooxy)androst-5-en-17-oneGenerator
(3-beta)-3-(Sulphooxy)androst-5-en-17-oneGenerator
(3-β)-3-(sulfooxy)androst-5-en-17-oneGenerator
(3-β)-3-(sulphooxy)androst-5-en-17-oneGenerator
(3beta)-3-(Sulfooxy)-androst-5-en-17-oneHMDB
17-Oxoandrost-5-en-3-yl hydrogen sulfateHMDB
17-Oxoandrost-5-en-3-yl hydrogen sulphateHMDB
17-Oxoandrost-5-en-3b-yl hydrogen sulfateHMDB
17-Oxoandrost-5-en-3b-yl hydrogen sulphateHMDB
17-Oxoandrost-5-en-3beta-yl hydrogen sulfateHMDB
3-b-Hydroxyandrost-5-en-17-one 3-sulfateHMDB
3-b-Hydroxyandrost-5-en-17-one 3-sulphateHMDB
3-beta-Hydroxyandrost-5-en-17-one 3-sulfateHMDB
3-beta-Hydroxyandrost-5-en-17-one 3-sulphateHMDB
3b-Hydroxy-androst-5-en-17-one hydrogen sulfateHMDB
3b-Hydroxy-androst-5-en-17-one hydrogen sulphateHMDB
3b-Hydroxyandrost-5-en-17-one 3-sulfateHMDB
3b-Hydroxyandrost-5-en-17-one 3-sulphateHMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulfateHMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulphateHMDB
3beta-Hydroxyandrost-5-en-17-one 3-sulphateHMDB
Dehydroepiandrosterone-3-sulfateHMDB
Dehydroepiandrosterone-3-sulphateHMDB
Dehydroisoandrosterone sulphateHMDB
DHEA sulphateHMDB
Formylisoglutamic acidHMDB
Prasterone sulphateHMDB
Prasterone-3-sulfateHMDB
Prasterone-3-sulphateHMDB
Chemical FormulaC19H28O5S
Average Molecular Weight368.488
Monoisotopic Molecular Weight368.165744696
IUPAC Name[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonic acid
Traditional Namedehydroepiandrosterone sulfate
CAS Registry Number651-48-9
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 KeyInChIKey=CZWCKYRVOZZJNM-USOAJAOKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSulfated steroids
Direct ParentSulfated steroids
Alternative Parents
Substituents
  • Sulfated steroid
  • 3-sulfated steroid
  • Sulfated steroid skeleton
  • Androstane-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • Delta-5-steroid
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug or steroid metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0081 mg/mLALOGPS
logP0.49ALOGPS
logP3.42ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.65 m3·mol-1ChemAxon
Polarizability39.86 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
17-Beta Hydroxysteroid Dehydrogenase III DeficiencySMP00356Not Available
Androgen and Estrogen MetabolismSMP00068map00150
Aromatase deficiencySMP00565Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.47 +/- 1.20 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified30.123-42.61 uMInfant (0 - <2 months old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified0.81-16.28 uMInfant (2 - <6 months old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified0.27-4.89 uMInfant (6 months - <1 year old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified0-3.26 uMChildren (1 - <6 years old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified0.27-4.34 uMChildren (6 - <9 years old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified0.81-7.60 uMChildren (9 - <13 years old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified1.63-13.03 uMAdolescent (13 - <16 years old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified4.07-16.01 uMAdolescent (16 - <19 years old)Female
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified3.53-16.01 uMAdolescent (16 - <19 years old)Male
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified4.5 (1.4-8.2) uMAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified1.25 (0.0026-2.52) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.34 +/- 0.23 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.63 +/- 2.14 uMAdult (>18 years old)FemalePolycystic ovary syndrome (PCOS) details
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Lung cancer
details
BloodDetected and Quantified6.54 +/- 2.55 uMAdult (>18 years old)FemaleAlzheimer's disease details
BloodDetected and Quantified9.8 +/- 1.3 uMAdult (>18 years old)FemaleHirsutism details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleEpithelial ovarian cancer details
UrineDetected and Quantified0.28 +/- 0.082 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.84 +/- 0.51 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.43 +/- 0.10 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
UrineDetected and Quantified1.56 +/- 0.041 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
Associated Disorders and Diseases
Disease References
Polycystic ovary syndrome
  1. Yildiz BO, Woods KS, Stanczyk F, Bartolucci A, Azziz R: Stability of adrenocortical steroidogenesis over time in healthy women and women with polycystic ovary syndrome. J Clin Endocrinol Metab. 2004 Nov;89(11):5558-62. [15531511 ]
Rheumatoid arthritis
  1. Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8. [15249323 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00518
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022381
KNApSAcK IDNot Available
Chemspider ID12074
KEGG Compound IDC04555
BioCyc IDDEHYDRO-EPIANDROSTERONE-SULFATE
BiGG ID44038
Wikipedia LinkDehydroepiandrosterone sulfate
NuGOwiki LinkHMDB01032
Metagene LinkHMDB01032
METLIN ID4095
PubChem Compound12594
PDB IDNot Available
ChEBI ID16814
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chang HJ, Shi R, Rehse P, Lin SX: Identifying androsterone (ADT) as a cognate substrate for human dehydroepiandrosterone sulfotransferase (DHEA-ST) important for steroid homeostasis: structure of the enzyme-ADT complex. J Biol Chem. 2004 Jan 23;279(4):2689-96. Epub 2003 Oct 21. [14573603 ]
  2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  3. Cutolo M, Sulli A, Capellino S, Villaggio B, Montagna P, Pizzorni C, Paolino S, Seriolo B, Felli L, Straub RH: Anti-TNF and sex hormones. Ann N Y Acad Sci. 2006 Jun;1069:391-400. [16855166 ]
  4. Clauss SB, Holmes KW, Hopkins P, Stein E, Cho M, Tate A, Johnson-Levonas AO, Kwiterovich PO: Efficacy and safety of lovastatin therapy in adolescent girls with heterozygous familial hypercholesterolemia. Pediatrics. 2005 Sep;116(3):682-8. [16140708 ]
  5. Gordon GB, Bush TL, Helzlsouer KJ, Miller SR, Comstock GW: Relationship of serum levels of dehydroepiandrosterone and dehydroepiandrosterone sulfate to the risk of developing postmenopausal breast cancer. Cancer Res. 1990 Jul 1;50(13):3859-62. [2141293 ]
  6. Roberts E: The importance of being dehydroepiandrosterone sulfate (in the blood of primates): a longer and healthier life? Biochem Pharmacol. 1999 Feb 15;57(4):329-46. [9933021 ]
  7. Gu H, Li Y, Rong L: [The effect of sodium prasterone sulfate on lactation] Zhonghua Fu Chan Ke Za Zhi. 1995 Apr;30(4):197-9. [7664601 ]
  8. Milewich L, Sontheimer RD, Herndon JH Jr: Steroid sulfatase activity in epidermis of acne-prone and non-acne-prone skin of patients with acne vulgaris. Arch Dermatol. 1990 Oct;126(10):1312-4. [2145810 ]
  9. Valle LD, Toffolo V, Nardi A, Fiore C, Bernante P, Di Liddo R, Parnigotto PP, Colombo L: Tissue-specific transcriptional initiation and activity of steroid sulfatase complementing dehydroepiandrosterone sulfate uptake and intracrine steroid activations in human adipose tissue. J Endocrinol. 2006 Jul;190(1):129-39. [16837617 ]
  10. Zappulla F, Ventura D, Capelli M, Cassio A, Balsamo A, Frejaville E, Bolelli G, Cacciari E: Gonadal and adrenal secretion of dehydroepiandrosterone sulfate in prepubertal and pubertal subjects. J Endocrinol Invest. 1981 Apr-Jun;4(2):197-202. [6268694 ]
  11. Ankarberg C, Norjavaara E: Diurnal rhythm of testosterone secretion before and throughout puberty in healthy girls: correlation with 17beta-estradiol and dehydroepiandrosterone sulfate. J Clin Endocrinol Metab. 1999 Mar;84(3):975-84. [10084582 ]
  12. Sipila S, Heikkinen E, Cheng S, Suominen H, Saari P, Kovanen V, Alen M, Rantanen T: Endogenous hormones, muscle strength, and risk of fall-related fractures in older women. J Gerontol A Biol Sci Med Sci. 2006 Jan;61(1):92-6. [16456199 ]
  13. Benvenga S, Smedile G, Lo Giudice F, Trimarchi F: Testicular adrenal rests: evidence for luteinizing hormone receptors and for distinct types of testicular nodules differing for their autonomization. Eur J Endocrinol. 1999 Sep;141(3):231-7. [10474120 ]
  14. Rainey WE, Rehman KS, Carr BR: The human fetal adrenal: making adrenal androgens for placental estrogens. Semin Reprod Med. 2004 Nov;22(4):327-36. [15635500 ]
  15. Zouboulis CC, Degitz K: Androgen action on human skin -- from basic research to clinical significance. Exp Dermatol. 2004;13 Suppl 4:5-10. [15507105 ]
  16. De Pergola G, Zamboni M, Sciaraffia M, Turcato E, Pannacciulli N, Armellini F, Giorgino F, Perrini S, Bosello O, Giorgino R: Body fat accumulation is possibly responsible for lower dehydroepiandrosterone circulating levels in premenopausal obese women. Int J Obes Relat Metab Disord. 1996 Dec;20(12):1105-10. [8968856 ]
  17. Coulter CL, Jaffe RB: Functional maturation of the primate fetal adrenal in vivo: 3. Specific zonal localization and developmental regulation of CYP21A2 (P450c21) and CYP11B1/CYP11B2 (P450c11/aldosterone synthase) lead to integrated concept of zonal and temporal steroid biosynthesis. Endocrinology. 1998 Dec;139(12):5144-50. [9832454 ]
  18. Wang HS, Wang TH, Soong YK: Low dose flutamide in the treatment of acne vulgaris in women with or without oligomenorrhea or amenorrhea. Changgeng Yi Xue Za Zhi. 1999 Sep;22(3):423-32. [10584414 ]
  19. Ibanez L, Potau N, Marcos MV, de Zegher F: Exaggerated adrenarche and hyperinsulinism in adolescent girls born small for gestational age. J Clin Endocrinol Metab. 1999 Dec;84(12):4739-41. [10599744 ]
  20. Cappola AR, Xue QL, Walston JD, Leng SX, Ferrucci L, Guralnik J, Fried LP: DHEAS levels and mortality in disabled older women: the Women's Health and Aging Study I. J Gerontol A Biol Sci Med Sci. 2006 Sep;61(9):957-62. [16960027 ]
  21. Jaquish CE, Blangero J, Haffner SM, Stern MP, Maccluer JW: Quantitative genetics of dehydroepiandrosterone sulfate and its relation to possible cardiovascular disease risk factors in Mexican Americans. Hum Hered. 1996 Nov-Dec;46(6):301-9. [8956025 ]

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Phosphoadenosine phosphosulfate + Dehydroepiandrosterone → Adenosine 3',5'-diphosphate + Dehydroepiandrosterone sulfatedetails
General function:
Involved in catalytic activity
Specific function:
Conversion of sulfated steroid precursors to estrogens during pregnancy.
Gene Name:
STS
Uniprot ID:
P08842
Molecular weight:
65491.72
Reactions
Dehydroepiandrosterone sulfate + Water → Dehydroepiandrosterone + Oat gumdetails
Dehydroepiandrosterone sulfate + Water → Dehydroepiandrosterone + Oat gumdetails