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Record Information
Version1.0
Creation Date2016-09-30 22:19:22 UTC
Update Date2020-06-04 23:02:28 UTC
MCDB ID BMDB0000077
Secondary Accession Numbers
  • BMDB00077
Metabolite Identification
Common NameDehydroepiandrosterone
DescriptionDehydroepiandrosterone, also known as 5-androsten-3b-ol-17-one or diandron, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, dehydroepiandrosterone is considered to be a steroid lipid molecule. Dehydroepiandrosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Dehydroepiandrosterone participates in a number of enzymatic reactions, within cattle. In particular, Dehydroepiandrosterone can be biosynthesized from 17a-hydroxypregnenolone through its interaction with the enzyme steroid 17-alpha-hydroxylase/17,20 lyase. In addition, Dehydroepiandrosterone can be converted into androstenedione through the action of the enzyme 3-beta-HSD 1. In cattle, dehydroepiandrosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Dehydroepiandrosterone is a potentially toxic compound. Dehydroepiandrosterone has been found to be associated with several diseases known as rheumatoid arthritis, antley-bixler syndrome with genital anomalies and disordered steroidogenesis, adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency, and adrenal insufficiency, congenital, with 46,xy sex reversal, partial or complete; also dehydroepiandrosterone has been linked to the inborn metabolic disorders including 21-hydroxylase deficiency.
Structure
Thumb
Synonyms
ValueSource
3-BETA-HYDROXY-5-androsten-17-oneChEBI
3beta-Hydroxyandrost-5-en-17-oneChEBI
DehydroisoandrosteroneChEBI
DHAChEBI
DHEAChEBI
IntrarosaChEBI
PrasteroneChEBI
BiolaifKegg
3-b-HYDROXY-5-androsten-17-oneGenerator
3-Β-hydroxy-5-androsten-17-oneGenerator
3b-Hydroxyandrost-5-en-17-oneGenerator
3Β-hydroxyandrost-5-en-17-oneGenerator
(+)-DehydroisoandrosteroneHMDB
(3-beta)-3-Hydroxyandrost-5-en-17-oneHMDB
(3beta)-3-Hydroxy-androst-5-en-17-oneHMDB
(3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-oneHMDB
17-ChetovisHMDB
17-HormoforinHMDB
3-beta-Hydroxyandrost-5-en-17-oneHMDB
3b-Hydroxy-D5-androsten-17-oneHMDB
3beta-Hydroxy-5-androsten-17-oneHMDB
3beta-Hydroxy-androst-5-en-17-oneHMDB
3beta-Hydroxy-D5-androsten-17-oneHMDB
5,6-DehydroisoandrosteroneHMDB
5,6-DidehydroisoandrosteroneHMDB
5-Androsten-3-beta-ol-17-oneHMDB
5-Androsten-3b-ol-17-oneHMDB
5-Androsten-3beta-ol-17-oneHMDB
5-Dehydro-epiandrosteroneHMDB
5-DehydroepiandrosteroneHMDB
AndrestenolHMDB
Androst-5-ene-3b-ol-17-oneHMDB
Androst-5-ene-3beta-ol-17-oneHMDB
Androsten-3beta-ol-17-oneHMDB
AndrostenoloneHMDB
AstenileHMDB
D5-Androsten-3b-ol-17-oneHMDB
D5-Androsten-3beta-ol-17-oneHMDB
DeandrosHMDB
Dehydro-epi-androsteroneHMDB
DiandronHMDB
DiandroneHMDB
HydroxyandrostenoneHMDB
PrasteronaHMDB
PrasteronumHMDB
PrestaraHMDB
PsicosteroneHMDB
trans-DehydroandrosteroneHMDB
Prasterone, 3 alpha-isomerHMDB
5 Androsten 3 beta hydroxy 17 oneHMDB
5-Androsten-3-beta-hydroxy-17-oneHMDB
5 Androsten 3 ol 17 oneHMDB
Prasterone, 3 alpha isomerHMDB
5-Androsten-3-ol-17-oneHMDB
EM-760DehydroandrosteroneHMDB
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number53-43-0
SMILESNot Available
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-USOAJAOKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.0002 +/- 0.0001 uM details
Detected and Quantified0.00012 +/- 0.00004 uM details
Detected and Quantified0.0002 +/- 0.0001 uM details
Detected and Quantified0.0002 uM details
Detected and Quantified0.00014 uM details
Detected and Quantified0.00042 uM details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000077
DrugBank IDDB01708
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021808
KNApSAcK IDNot Available
Chemspider ID8036443
KEGG Compound IDC01227
BioCyc ID3-BETA-HYDROXYANDROST-5-EN-17-ONE
BiGG ID37131
Wikipedia LinkDehydroepiandrosterone
METLIN ID5133
PubChem Compound5881
PDB IDNot Available
ChEBI ID28689
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. Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. [PubMed:17852390 ]
  2. Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. [PubMed:18412364 ]
  3. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]