Human Metabolome Database Version 3.5

Showing metabocard for Dehydroepiandrosterone (HMDB00077)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:52 -0700
HMDB ID HMDB00077
Secondary Accession Numbers None
Metabolite Identification
Common Name Dehydroepiandrosterone
Description Dehydroepiandrosterone (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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C19H28O2
Average Molecular Weight 288.4244
Monoisotopic Molecular Weight 288.20893014
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 Number 53-43-0
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 Key FMGSKLZLMKYGDP-INNQQZFDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Androgens and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Hydroxysteroids
  • a 3&beta;-hydroxy-&delta;<sup>5</sup>-steroid(Cyc)
Substituents
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Ketone
  • Secondary Alcohol
  • Sesquiterpene Backbone
Direct Parent Androgens and Derivatives
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 140 - 141 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.0635 mg/mL Not Available
LogP 3.23 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.044 g/L ALOGPS
LogP 3.53 ALOGPS
LogP 3.36 ChemAxon
LogS -3.82 ALOGPS
pKa (strongest acidic) 18.2 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 84.66 ChemAxon
Polarizability 33.2 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Muscle
  • Fibroblasts
  • Neuron
  • Placenta
  • Testes
  • Kidney
  • Liver
  • Epidermis
  • Brain
  • Prostate
  • Adrenal Gland
  • Adipose Tissue
  • Adrenal Cortex
  • Platelet
  • Gonads
Pathways
Name SMPDB Link KEGG Link
Androgen and Estrogen Metabolism SMP00068 map00150 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.020 +/- 0.011 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
0.001 (0.00034-0.0017) uM Children (1-13 year old) Female Normal
Blood Detected and Quantified
0.0087 (0.0035-0.013) uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
0.023 (0.005-0.042) uM Adult (>18 years old) Both Normal
  • The Merck Ma...
Cerebrospinal Fluid (CSF) Detected and Quantified
0.00101 (0.00002-0.002) uM Adult (>18 years old) Not Specified Normal
Saliva Detected and Quantified
0.0033 (0.0024-0.0090) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.10 (0.066-0.17) umol/mmol creatinine Adult (>18 years old) Male Normal
Urine Detected and Quantified
0.022 (0.017-0.041) umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.13 +/- 0.057 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0016 +/- 0.00026 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00114 +/- 0.000630 uM Adult (>18 years old) Not Specified Leuprolide acetate-induce hypogonadism
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00127 +/- 0.00128 uM Adult (>18 years old) Not Specified Leuprolide acetate-induced hypogonadism with testosterone replacment
Urine Detected and Quantified 0.00032 +/- 0.000065 umol/mmol creatinine Adult (>18 years old) Both Comment Rheumatoid arthritis
Urine Detected and Quantified 0.00066 +/- 0.00021 umol/mmol creatinine Adult (>18 years old) Both Comment Rheumatoid arthritis
Urine Detected and Quantified 0.00034 +/- 0.000078 umol/mmol creatinine Adult (>18 years old) Both Comment Systemic lupus erythematosus (SLE)
Urine Detected and Quantified 0.0011 +/- 0.00026 umol/mmol creatinine Adult (>18 years old) Both Comment Systemic lupus erythematosus (SLE)
Associated Disorders and Diseases
Disease References
Rheumatoid arthritis
  • 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 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB021808
      KNApSAcK ID Not Available
      Chemspider ID 8036443 Link_out
      KEGG Compound ID C01227 Link_out
      BioCyc ID DEHYDRO-EPIANDROSTERONE-SULFATE Link_out
      BiGG ID 37131 Link_out
      Wikipedia Link Dehydroepiandrosterone Link_out
      NuGOwiki Link HMDB00077 Link_out
      Metagene Link HMDB00077 Link_out
      METLIN ID 5133 Link_out
      PubChem Compound 9860744 Link_out
      PDB ID Not Available
      ChEBI ID 220467 Link_out
      References
      Synthesis Reference Nguyen 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. 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 Link_out
      2. 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 Link_out
      3. 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 Link_out
      4. 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 Link_out
      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 Link_out
      6. 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 Link_out
      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 Link_out
      8. Finlay EM, Morton MS, Gaskell SJ: Identification and quantification of dehydroepiandrosterone sulphate in saliva. Steroids. 1982 Jan;39(1):63-71. Pubmed: 6210977 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: Sulfotransferase family cytosolic 2B member 1
      Reactions:
      Phosphoadenosine phosphosulfate + Dehydroepiandrosterone unknown Adenosine 3',5'-diphosphate + Dehydroepiandrosterone sulfate details
      Gene Name: SULT2B1
      Uniprot ID: O00204 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Steryl-sulfatase
      Reactions:
      Dehydroepiandrosterone sulfate + Water unknown Dehydroepiandrosterone + Oat gum details
      Dehydroepiandrosterone sulfate + Water unknown Dehydroepiandrosterone + Oat gum details
      Gene Name: STS
      Uniprot ID: P08842 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cholesterol 7-alpha-monooxygenase
      Reactions:
      Dehydroepiandrosterone + Oxygen + NADPH + Hydrogen Ion unknown 7a-Hydroxydehydroepiandrosterone + NADP + Water details
      Gene Name: CYP7A1
      Uniprot ID: P22680 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Steroid 17-alpha-hydroxylase/17,20 lyase
      Reactions:
      17a-Hydroxypregnenolone + Reduced acceptor + Oxygen unknown Dehydroepiandrosterone + Acetic acid + Acceptor + Water details
      Gene Name: CYP17A1
      Uniprot ID: P05093 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1
      Reactions:
      Dehydroepiandrosterone + NAD unknown Androstenedione + NADH + Hydrogen Ion details
      Gene Name: HSD3B1
      Uniprot ID: P14060 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2
      Reactions:
      Dehydroepiandrosterone + NAD unknown Androstenedione + NADH + Hydrogen Ion details
      Gene Name: HSD3B2
      Uniprot ID: P26439 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Transporters
      Name: Solute carrier organic anion transporter family member 1B3
      Reactions: Not Available
      Gene Name: SLCO1B3
      Uniprot ID: Q9NPD5 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Solute carrier organic anion transporter family member 1B1
      Reactions: Not Available
      Gene Name: SLCO1B1
      Uniprot ID: Q9Y6L6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Solute carrier family 22 member 7
      Reactions: Not Available
      Gene Name: SLC22A7
      Uniprot ID: Q9Y694 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA