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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-06-19 02:43:37 UTC
HMDB IDHMDB0001032
Secondary Accession Numbers
  • HMDB01032
Metabolite Identification
Common NameDehydroepiandrosterone sulfate
DescriptionDehydroepiandrosterone sulfate or DHEA-S 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 DHEA-S with levels that are about 300 times higher than those of free DHEA. Orally-ingested DHEA is converted into its sulfate when passing through the 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 DHEA-S is preferable to DHEA since levels are more stable. DHEA (from which DHEA-S 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. 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 the 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
Dehydroepiandrosterone sulfuric acidGenerator
Dehydroepiandrosterone sulphuric acidGenerator
17-Ketoandrost-5-en-3b-yl sulfateGenerator
17-Ketoandrost-5-en-3b-yl sulfuric acidGenerator
17-Ketoandrost-5-en-3b-yl sulphateGenerator
17-Ketoandrost-5-en-3b-yl sulphuric acidGenerator
17-Ketoandrost-5-en-3beta-yl sulfuric acidGenerator
17-Ketoandrost-5-en-3beta-yl sulphateGenerator
17-Ketoandrost-5-en-3beta-yl sulphuric acidGenerator
17-Ketoandrost-5-en-3β-yl sulfateGenerator
17-Ketoandrost-5-en-3β-yl sulfuric acidGenerator
17-Ketoandrost-5-en-3β-yl sulphateGenerator
17-Ketoandrost-5-en-3β-yl sulphuric acidGenerator
17-Oxoandrost-5-en-3b-yl hydrogen sulfateGenerator
17-Oxoandrost-5-en-3b-yl hydrogen sulfuric acidGenerator
17-Oxoandrost-5-en-3b-yl hydrogen sulphateGenerator
17-Oxoandrost-5-en-3b-yl hydrogen sulphuric acidGenerator
17-Oxoandrost-5-en-3beta-yl hydrogen sulfateGenerator
17-Oxoandrost-5-en-3beta-yl hydrogen sulfuric acidGenerator
17-Oxoandrost-5-en-3beta-yl hydrogen sulphuric acidGenerator
17-Oxoandrost-5-en-3β-yl hydrogen sulfateGenerator
17-Oxoandrost-5-en-3β-yl hydrogen sulfuric acidGenerator
17-Oxoandrost-5-en-3β-yl hydrogen sulphateGenerator
17-Oxoandrost-5-en-3β-yl hydrogen sulphuric acidGenerator
3-O-SulphodehydroepiandrosteroneGenerator
3b-Hydroxyandrost-5-en-17-one 3-sulfateGenerator
3b-Hydroxyandrost-5-en-17-one 3-sulfuric acidGenerator
3b-Hydroxyandrost-5-en-17-one 3-sulphateGenerator
3b-Hydroxyandrost-5-en-17-one 3-sulphuric acidGenerator
3beta-Hydroxyandrost-5-en-17-one 3-sulfuric acidGenerator
3beta-Hydroxyandrost-5-en-17-one 3-sulphateGenerator
3beta-Hydroxyandrost-5-en-17-one 3-sulphuric acidGenerator
3β-hydroxyandrost-5-en-17-one 3-sulfateGenerator
3β-hydroxyandrost-5-en-17-one 3-sulfuric acidGenerator
3β-hydroxyandrost-5-en-17-one 3-sulphateGenerator
3β-hydroxyandrost-5-en-17-one 3-sulphuric acidGenerator
Androst-5-en-17-on-3b-yl sulfateGenerator
Androst-5-en-17-on-3b-yl sulfuric acidGenerator
Androst-5-en-17-on-3b-yl sulphateGenerator
Androst-5-en-17-on-3b-yl sulphuric acidGenerator
Androst-5-en-17-on-3beta-yl sulfateGenerator
Androst-5-en-17-on-3beta-yl sulphateGenerator
Androst-5-en-17-on-3beta-yl sulphuric acidGenerator
Androst-5-en-17-on-3β-yl sulfateGenerator
Androst-5-en-17-on-3β-yl sulfuric acidGenerator
Androst-5-en-17-on-3β-yl sulphateGenerator
Androst-5-en-17-on-3β-yl sulphuric acidGenerator
Dehydroepiandrosterone 3-sulfuric acidGenerator
Dehydroepiandrosterone 3-sulphateGenerator
Dehydroepiandrosterone 3-sulphuric acidGenerator
Dehydroepiandrosterone monosulfuric acidGenerator
Dehydroepiandrosterone monosulphateGenerator
Dehydroepiandrosterone monosulphuric acidGenerator
Dehydroisoandrosterone sulfuric acidGenerator
Dehydroisoandrosterone sulphateGenerator
Dehydroisoandrosterone sulphuric acidGenerator
Dehydroisoandrosterone-3-sulfuric acidGenerator
Dehydroisoandrosterone-3-sulphateGenerator
Dehydroisoandrosterone-3-sulphuric acidGenerator
DHEA sulfuric acidGenerator
DHEA sulphateGenerator
DHEA sulphuric acidGenerator
Prasterone sulfuric acidGenerator
Prasterone sulphateGenerator
Prasterone sulphuric acidGenerator
(3beta)-3-(Sulfooxy)-androst-5-en-17-oneHMDB
17-Oxoandrost-5-en-3-yl hydrogen sulfateHMDB
17-Oxoandrost-5-en-3-yl hydrogen sulphateHMDB
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
3beta-Hydroxy-androst-5-en-17-one hydrogen sulfateHMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulphateHMDB
Dehydroepiandrosterone-3-sulfateHMDB
Dehydroepiandrosterone-3-sulphateHMDB
Formylisoglutamic acidHMDB
Prasterone-3-sulfateHMDB
Prasterone-3-sulphateHMDB
DHA sulfateMeSH
Sulfate, dehydroisoandrosteroneMeSH
Sulfate, prasteroneMeSH
Sulfate, dheaMeSH
Sulfate, dehydroepiandrosteroneMeSH
Sulfate, dhaMeSH
Chemical FormulaC19H28O5S
Average Molecular Weight368.488
Monoisotopic Molecular Weight368.165744696
IUPAC Name[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-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
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 KeyCZWCKYRVOZZJNM-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 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.65 m³·mol⁻¹ChemAxon
Polarizability39.85 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0097000000-e6d4f60e9803940d2f55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0049000000-f9a938b029283c157bdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0091000000-c2b83d86ae8174524e1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5792000000-20638b1484fe342eb3c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-79344bc1ba3ea2c26db7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1092000000-3b129a6c30b2629e1661View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008i-6090000000-35cc2726715438281170View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 but not Quantified Adult (>18 years old)Female
Normal
details
BloodDetected and Quantified<0.500 uMNot SpecifiedBothNormal details
BloodDetected and Quantified0.950-11.669 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified4.5 (1.4-8.2) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.950 - 1.167 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified42.0638-105.0238 uMNewborn (0-30 days old)MaleAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified3.63 +/- 2.14 uMAdult (>18 years old)FemalePolycystic ovary syndrome (PCOS) details
BloodDetected but not Quantified Adult (>18 years old)Both
Lung cancer
details
BloodDetected and Quantified3.400-15 uMAdult (>18 years old)MaleX-linked ichthyosis details
BloodDetected but not Quantified Adult (>18 years old)Female
Schizophrenia
details
BloodDetected and Quantified5.493 uMAdult (>18 years old)Female
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified6.54 +/- 2.55 uMAdult (>18 years old)FemaleAlzheimer's disease details
BloodDetected and Quantified20 uMNewborn (0-30 days old)Female11-beta-hydroxylase deficiency details
BloodDetected and Quantified2.000-10.400 uMChildren (1-13 years old)Both11-beta-hydroxylase deficiency details
BloodDetected and Quantified<0.02 uMAdult (>18 years old)FemaleLipoid Adrenal Hyperplasia details
BloodDetected and Quantified<0.02 uMAdolescent (13-18 years old)FemaleLipoid Adrenal Hyperplasia details
BloodDetected and Quantified<0.810 uMChildren (1-13 years old)Female
Aromatase deficiency
details
BloodDetected and Quantified0.0621 uMAdult (>18 years old)Female
Adrenal hyperplasia, congenital, due to 17-alpha-hydroxylase deficiency
details
BloodDetected and Quantified0.104 uMAdolescent (13-18 years old)Female
Adrenal hyperplasia, congenital, due to 17-alpha-hydroxylase deficiency
details
BloodDetected and Quantified9.8 +/- 1.3 uMAdult (>18 years old)FemaleHirsutism details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected but not Quantified Adult (>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
11-beta-Hydroxylase deficiency
  1. Burren CP, Montalto J, Yong AB, Batch JA: CYP11 beta 1 (11-beta-hydroxylase) deficiency in congenital adrenal hyperplasia. J Paediatr Child Health. 1996 Oct;32(5):433-8. [PubMed:8933406 ]
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
  1. Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ]
  2. Guven A, Polat S: Testicular Adrenal Rest Tumor in Two Brothers with a Novel Mutation in the 3-Beta-Hydroxysteroid Dehydrogenase-2 Gene. J Clin Res Pediatr Endocrinol. 2017 Mar 1;9(1):85-90. doi: 10.4274/jcrpe.3306. Epub 2016 Jul 29. [PubMed:27476613 ]
Alzheimer's disease
  1. Reichman ME, Judd JT, Longcope C, Schatzkin A, Clevidence BA, Nair PP, Campbell WS, Taylor PR: Effects of alcohol consumption on plasma and urinary hormone concentrations in premenopausal women. J Natl Cancer Inst. 1993 May 5;85(9):722-7. [PubMed:8478958 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Schizophrenia
  1. Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Lung Cancer
  1. Chen Y, Ma Z, Min L, Li H, Wang B, Zhong J, Dai L: Biomarker identification and pathway analysis by serum metabolomics of lung cancer. Biomed Res Int. 2015;2015:183624. doi: 10.1155/2015/183624. Epub 2015 Apr 16. [PubMed:25961003 ]
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. [PubMed: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. [PubMed:15249323 ]
Congenital Adrenal Hyperplasia, due to 17-Hydroxylase-Deficiency
  1. Kim SM, Rhee JH: A case of 17 alpha-hydroxylase deficiency. Clin Exp Reprod Med. 2015 Jun;42(2):72-6. doi: 10.5653/cerm.2015.42.2.72. Epub 2015 Jun 30. [PubMed:26161337 ]
Aromatase deficiency
  1. Mullis PE, Yoshimura N, Kuhlmann B, Lippuner K, Jaeger P, Harada H: Aromatase deficiency in a female who is compound heterozygote for two new point mutations in the P450arom gene: impact of estrogens on hypergonadotropic hypogonadism, multicystic ovaries, and bone densitometry in childhood. J Clin Endocrinol Metab. 1997 Jun;82(6):1739-45. doi: 10.1210/jcem.82.6.3994. [PubMed:9177373 ]
Lipoid Congenital Adrenal Hyperplasia
  1. Fujieda K, Tajima T, Nakae J, Sageshima S, Tachibana K, Suwa S, Sugawara T, Strauss JF 3rd: Spontaneous puberty in 46,XX subjects with congenital lipoid adrenal hyperplasia. Ovarian steroidogenesis is spared to some extent despite inactivating mutations in the steroidogenic acute regulatory protein (StAR) gene. J Clin Invest. 1997 Mar 15;99(6):1265-71. doi: 10.1172/JCI119284. [PubMed:9077535 ]
X-linked ichthyosis
  1. Lykkesfeldt G, Bennett P, Lykkesfeldt AE, Micic S, Moller S, Svenstrup B: Abnormal androgen and oestrogen metabolism in men with steroid sulphatase deficiency and recessive X-linked ichthyosis. Clin Endocrinol (Oxf). 1985 Oct;23(4):385-93. [PubMed:3864567 ]
Hirsutism
  1. Gilad S, Chayen R, Tordjman K, Kisch E, Stern N: Assessment of 5 alpha-reductase activity in hirsute women: comparison of serum androstanediol glucuronide with urinary androsterone and aetiocholanolone excretion. Clin Endocrinol (Oxf). 1994 Apr;40(4):459-64. [PubMed:8187312 ]
Associated OMIM IDs
  • 184700 (Polycystic ovary syndrome)
  • 104300 (Alzheimer's disease)
  • 211980 (Lung Cancer)
  • 181500 (Schizophrenia)
  • 201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
  • 202010 (11-beta-Hydroxylase deficiency)
  • 613546 (Aromatase deficiency)
  • 202110 (Congenital Adrenal Hyperplasia, due to 17-Hydroxylase-Deficiency)
  • 308100 (X-linked ichthyosis)
  • 201710 (Lipoid Congenital Adrenal Hyperplasia)
  • 114500 (Colorectal cancer)
  • 180300 (Rheumatoid arthritis)
DrugBank IDDB05804
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022381
KNApSAcK IDNot Available
Chemspider ID12074
KEGG Compound IDC04555
BioCyc IDDEHYDRO-EPIANDROSTERONE-SULFATE
BiGG ID44038
Wikipedia LinkDehydroepiandrosterone_sulfate
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. [PubMed: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. doi: 10.1038/nature07762. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:2145810 ]
  9. Dalla Valle L, 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. [PubMed:16837617 ]
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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