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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:52 UTC
HMDB IDHMDB00077
Secondary Accession NumbersNone
Metabolite Identification
Common NameDehydroepiandrosterone
DescriptionDehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue and the brain. DHEA is structurally similar to, and is a precursor of, androstenedione, testosterone, estradiol, estrone and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate- DEHAS) before secretion. DHEAS is the sulfated version of DHEA; - this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEAS with levels that are about 300 times higher than free DHEA. Blood measurements of DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEAS.
Structure
Thumb
Synonyms
  1. (+)-Dehydroisoandrosterone
  2. (3-beta)-3-Hydroxyandrost-5-en-17-one
  3. (3beta)-3-hydroxy-Androst-5-en-17-one
  4. (3beta,16alpha)-3,16-dihydroxy-androst-5-en-17-one
  5. 17-Chetovis
  6. 17-Hormoforin
  7. 3-beta-Hydroxy-5-androsten-17-one
  8. 3-beta-Hydroxyandrost-5-en-17-one
  9. 3b-Hydroxy-D5-androsten-17-one
  10. 3b-Hydroxyandrost-5-en-17-one
  11. 3beta-hydroxy-5-androsten-17-one
  12. 3beta-hydroxy-Androst-5-en-17-one
  13. 3beta-Hydroxy-D5-androsten-17-one
  14. 3beta-Hydroxyandrost-5-en-17-one
  15. 5,6-Dehydroisoandrosterone
  16. 5,6-Didehydroisoandrosterone
  17. 5-Androsten-3-beta-ol-17-one
  18. 5-Androsten-3b-ol-17-one
  19. 5-Androsten-3beta-ol-17-one
  20. 5-Dehydro-Epiandrosterone
  21. 5-Dehydroepiandrosterone
  22. Andrestenol
  23. Androst-5-ene-3b-ol-17-one
  24. Androst-5-ene-3beta-ol-17-one
  25. Androsten-3beta-ol-17-one
  26. Androstenolone
  27. Astenile
  28. D5-Androsten-3b-ol-17-one
  29. D5-Androsten-3beta-ol-17-one
  30. Deandros
  31. Dehydro-epi-androsterone
  32. Dehydroepiandrosterone
  33. Dehydroisoandrosterone
  34. Diandron
  35. Diandrone
  36. Hydroxyandrostenone
  37. Prasterona
  38. Prasterone
  39. Prasteronum
  40. Prestara
  41. Psicosterone
  42. trans-Dehydroandrosterone
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
IUPAC Name(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
Traditional IUPAC Name(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
CAS Registry Number53-43-0
SMILES
C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CCC2=O
InChI Identifier
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14?,15?,16?,18-,19-/m0/s1
InChI KeyFMGSKLZLMKYGDP-INNQQZFDSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassAndrogens and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Hydroxysteroids
  • a 3β-hydroxy-δ5-steroid(Cyc)
Substituents
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Ketone
  • Secondary Alcohol
  • Sesquiterpene Backbone
Direct ParentAndrogens and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Androgen and estrogen metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140 - 141 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0635 mg/mLNot Available
LogP3.23HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility0.044 g/LALOGPS
logP3.53ALOGPS
logP3.36ChemAxon
logS-3.8ALOGPS
pKa (strongest acidic)18.2ChemAxon
pKa (strongest basic)-1.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count0ChemAxon
refractivity84.66ChemAxon
polarizability33.2ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Brain
  • Epidermis
  • Fibroblasts
  • Gonads
  • Kidney
  • Liver
  • Muscle
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Androgen and Estrogen MetabolismSMP00068map00150
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.020 +/- 0.011 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.001 (0.00034-0.0017) uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified0.0087 (0.0035-0.013) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.023 (0.005-0.042) uMAdult (>18 years old)BothNormal
    • The Merck Manual,...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00101 (0.00002-0.002) uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified0.0033 (0.0024-0.0090) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.10 (0.066-0.17) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.022 (0.017-0.041) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.13 +/- 0.057 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0016 +/- 0.00026 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.00114 +/- 0.000630 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00127 +/- 0.00128 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism with testosterone replacment details
UrineDetected and Quantified0.00032 +/- 0.000065 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.00066 +/- 0.00021 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.00034 +/- 0.000078 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
UrineDetected and Quantified0.0011 +/- 0.00026 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
Associated Disorders and Diseases
Disease References
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
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021808
KNApSAcK IDNot Available
Chemspider ID8036443
KEGG Compound IDC01227
BioCyc IDDEHYDRO-EPIANDROSTERONE-SULFATE
BiGG ID37131
Wikipedia LinkDehydroepiandrosterone
NuGOwiki LinkHMDB00077
Metagene LinkHMDB00077
METLIN ID5133
PubChem Compound9860744
PDB IDNot Available
ChEBI ID220467
References
Synthesis ReferenceNguyen Xuan Cuong; Nguyen Van Dan. Synthesis of dehydroepiandrosterone (DHA) from 16-dehydropregnenolone acetate (DPA). Tap Chi Duoc Hoc (1983), (4), 12-14.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82. Pubmed: 1620285
  2. Robinzon B, Michael KK, Ripp SL, Winters SJ, Prough RA: Glucocorticoids inhibit interconversion of 7-hydroxy and 7-oxo metabolites of dehydroepiandrosterone: a role for 11beta-hydroxysteroid dehydrogenases? Arch Biochem Biophys. 2003 Apr 15;412(2):251-8. Pubmed: 12667489
  3. Rao MS, Subbarao V, Yeldandi AV, Reddy JK: Hepatocarcinogenicity of dehydroepiandrosterone in the rat. Cancer Res. 1992 May 15;52(10):2977-9. Pubmed: 1316232
  4. Saruc M, Yuceyar H, Ayhan S, Turkel N, Tuzcuoglu I, Can M: The association of dehydroepiandrosterone, obesity, waist-hip ratio and insulin resistance with fatty liver in postmenopausal women--a hyperinsulinemic euglycemic insulin clamp study. Hepatogastroenterology. 2003 May-Jun;50(51):771-4. Pubmed: 12828082
  5. Bamberg E, Aichinger A, Mitteregger G: In vitro metabolism of dehydroepiandrosterone and testosterone by canine hair follicle cells. Vet Dermatol. 2004 Feb;15(1):19-24. Pubmed: 14989701
  6. 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
  7. Weill-Engerer S, David JP, Sazdovitch V, Liere P, Schumacher M, Delacourte A, Baulieu EE, Akwa Y: In vitro metabolism of dehydroepiandrosterone (DHEA) to 7alpha-hydroxy-DHEA and Delta5-androstene-3beta,17beta-diol in specific regions of the aging brain from Alzheimer's and non-demented patients. Brain Res. 2003 Apr 18;969(1-2):117-25. Pubmed: 12676372
  8. Finlay EM, Morton MS, Gaskell SJ: Identification and quantification of dehydroepiandrosterone sulphate in saliva. Steroids. 1982 Jan;39(1):63-71. Pubmed: 6210977
  9. Uzieblo-Zyczkowska B, Sidlo E, Stelmaszuk T: [Dehydroepiandrosterone (DHEA)--slows down the aging process?] Pol Merkur Lekarski. 2005 Dec;19(114):831-4. Pubmed: 16521435
  10. Prost O, Nicollier M, Laurent R, Adessi GL: Estrone- and dehydroepiandrosterone-sulfatase activities in human female epidermis. Arch Dermatol Res. 1985;277(3):195-200. Pubmed: 3160310
  11. Friess E, Schiffelholz T, Steckler T, Steiger A: Dehydroepiandrosterone--a neurosteroid. Eur J Clin Invest. 2000 Dec;30 Suppl 3:46-50. Pubmed: 11281367
  12. Hakkinen A, Pakarinen A, Hannonen P, Kautiainen H, Nyman K, Kraemer WJ, Hakkinen K: Effects of prolonged combined strength and endurance training on physical fitness, body composition and serum hormones in women with rheumatoid arthritis and in healthy controls. Clin Exp Rheumatol. 2005 Jul-Aug;23(4):505-12. Pubmed: 16095120
  13. Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. Pubmed: 14625002
  14. Kim SB, Hill M, Kwak YT, Hampl R, Jo DH, Morfin R: Neurosteroids: Cerebrospinal fluid levels for Alzheimer's disease and vascular dementia diagnostics. J Clin Endocrinol Metab. 2003 Nov;88(11):5199-206. Pubmed: 14602750
  15. Chalbot S, Morfin R: Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives. Drug Metab Dispos. 2005 Apr;33(4):563-9. Epub 2005 Jan 13. Pubmed: 15650074
  16. Miller KK, Cai J, Ripp SL, Pierce WM Jr, Rushmore TH, Prough RA: Stereo- and regioselectivity account for the diversity of dehydroepiandrosterone (DHEA) metabolites produced by liver microsomal cytochromes P450. Drug Metab Dispos. 2004 Mar;32(3):305-13. Pubmed: 14977864
  17. Martina V, Benso A, Gigliardi VR, Masha A, Origlia C, Granata R, Ghigo E: Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol (Oxf). 2006 Mar;64(3):260-4. Pubmed: 16487434

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
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:
CYP7A1
Uniprot ID:
P22680
Molecular weight:
57660.155
Reactions
Dehydroepiandrosterone + Oxygen + NADPH + Hydrogen Ion → 7a-Hydroxydehydroepiandrosterone + NADP + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:
CYP17A1
Uniprot ID:
P05093
Molecular weight:
57369.995
Reactions
17a-Hydroxypregnenolone + Reduced acceptor + Oxygen → Dehydroepiandrosterone + Acetic acid + Acceptor + Waterdetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:
HSD3B1
Uniprot ID:
P14060
Molecular weight:
42251.25
Reactions
Dehydroepiandrosterone + NAD → Androstenedione + NADH + Hydrogen Iondetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
HSD3B2
Uniprot ID:
P26439
Molecular weight:
42051.845
Reactions
Dehydroepiandrosterone + NAD → Androstenedione + NADH + Hydrogen Iondetails

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular weight:
77402.2
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
General function:
Involved in transmembrane transport
Specific function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular weight:
60025.0