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Bovine Metabolome Database



Showing metabocard for Dehydroepiandrosterone (BMDB00077)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-06-10 15:32:00
Accession Number BMDB00077
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.
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-D5-androsten-17-one
  12. 3beta-Hydroxyandrost-5-en-17-one
  13. 3beta-hydroxy-5-androsten-17-one
  14. 3beta-hydroxy-Androst-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-Dehydroepiandrosterone
  21. 5-dehydro-Epiandrosterone
  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 IUPAC Name (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
Chemical Formula C19H28O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Mammalian_Metabolite
Species
  • ketone; secondary alcohol; alkene
Biofunction
  • Component of Androgen and estrogen metabolism
Application
Source
  • Endogenous
Average Molecular Weight 288.424
Monoisotopic Molecular Weight 288.208923
Isomeric SMILES C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CCC2=O
Canonical SMILES CC12CCC3C(CC=C4CC(O)CCC34C)C1CCC2=O
KEGG Compound ID C01227 Link Image
BioCyc ID DEHYDRO-EPIANDROSTERONE-SULFATE Link Image
BiGG ID 37131 Link Image
Wikipedia Link Dehydroepiandrosterone Link Image
METLIN ID 5133 Link Image
PubChem Compound 5881 Link Image
PubChem Substance 8153636 Link Image
ChEBI ID 28689 Link Image
CAS Registry Number 53-43-0
InChI Identifier InChI=1/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
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.
Melting Point (Experimental) 140-141 oC
Experimental Water Solubility 0.0635 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 0.0438 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity 3.23 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 3 [Predicted by PubChem via XLOGP]; 3.53 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
  • Cytoplasm
  • endoplasmic reticulum
Biofluid Location
  • Breast_Milk
Tissue Location
Tissue References
Adipose Tissue
Adrenal Cortex
Adrenal Gland
Brain
Epidermis
Fibroblasts
Gonads
Kidney
Liver
Muscle
Neuron
Placenta
Platelet
Prostate
Testes
Concentrations (Normal)
Biofluid Breast_Milk
Value 0.000227 +/- 7.766E-05 uM
Age N/A
Sex N/A
Condition Normal
Comments Whole milk (commercial).
References
Biofluid Breast_Milk
Value 0.000415 uM
Age N/A
Sex N/A
Condition Normal
Comments Whole milk.
References
Biofluid Breast_Milk
Value 0.000199 uM
Age N/A
Sex N/A
Condition Normal
Comments Half skimmed milk.
References
Biofluid Breast_Milk
Value 0.000142 uM
Age N/A
Sex N/A
Condition Normal
Comments Skimmed milk.
References
Biofluid Breast_Milk
Value 0.000183 +/- 6.241E-05 uM
Age N/A
Sex N/A
Condition Normal
Comments Half-Skimmed (commercial).
References
Biofluid Breast_Milk
Value 0.000118 +/- 4.299E-05 uM
Age N/A
Sex N/A
Condition Normal
Comments Skimmed (commercial).
References
Concentrations (Abnormal) Not Available
Pathway Names
  • Androgen and Estrogen Metabolism
HMDB Pathways
Name Androgen and Estrogen Metabolism
Image Show Link Image
KEGG Pathways
Name Androgen and Estrogen Metabolism
Image Show Link Image
SimCell Pathways
Name Androgen and Estrogen Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image