dehydroepiandrosterone (PAMDB120549)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120549
Identification
Name: dehydroepiandrosterone
Description:An androstanoid that is androst-5-ene substituted by a β-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3-BETA-HYDROXY-5-ANDROSTEN-17-ONE
  • 3beta-hydroxyandrost-5-en-17-one
  • 3beta-Hydroxyandrost-5-en-17-one
  • 3β-hydroxyandrost-5-en-17-one
  • 3beta-Hydroxyandrost-5-en-17-one
  • Dehydroepiandrosterone
  • Dehydroisoandrosterone
  • DHA
  • DHEA
  • Prasterone
Chemical Formula: C19H28O2
Average Molecular Weight: 288.429
Monoisotopic Molecular Weight: 288.20892
InChI Key: FMGSKLZLMKYGDP-USOAJAOKSA-N
InChI: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
CAS number: 53-43-0
IUPAC Name:3β-hydroxyandrost-5-en-17-one
Traditional IUPAC Name: dhea - dehydroepiandrosterone
SMILES:CC24(CCC(O)CC(=CC[CH]1([CH]3(CCC(=O)C(CC[CH]12)(C)3)))4)
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Steroids and steroid derivatives
Sub ClassAndrostane steroids
Direct Parent Androgens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular Framework Aliphatic homopolycyclic compounds
External Descriptors
  • a 3\u0026beta;-hydroxy-\u0026delta;\u003csup\u003e5\u003c/sup\u003e-steroid (3-BETA-HYDROXYANDROST-5-EN-17-ONE)
Physical Properties
State: Solid
Charge:0
Melting point: 140 - 141 °C
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 mg/mLALOGPS
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 Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.66 m3·mol-1ChemAxon
Polarizability33.2 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Water + 3-β-hydroxyandrost-5-en-17-one 3-sulfate → Hydrogen ion + Sulfate + dehydroepiandrosterone
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uk9-0190000000-c3794202067bedafc38fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053s-2920000000-ae96b214b1844b2bee11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-6900000000-019d22877fe66944e9efView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Ng MK, Nakhla S, Baoutina A, Jessup W, Handelsman DJ, Celermajer DS (2003)Dehydroepiandrosterone, an adrenal androgen, increases human foam cell formation: a potentially pro-atherogenic effect. Journal of the American College of Cardiology 42, Pubmed: 14662261
  • Narkwichean A, Jayaprakasan K, Maalouf WE, Hernandez-Medrano JH, Pincott-Allen C, Campbell BK (2014)Effects of dehydroepiandrosterone on in vivo ovine follicular development. Human reproduction (Oxford, England) 29, Pubmed: 24256992
  • Engdahl C, Lagerquist MK, Stubelius A, Andersson A, Studer E, Ohlsson C, Westberg L, Carlsten H, Forsblad-d'Elia H (2014)Role of androgen and estrogen receptors for the action of dehydroepiandrosterone (DHEA). Endocrinology 155, Pubmed: 24424045
  • Krysiak R, Frysz-Naglak D, Okopien B (2008)[Current views on the role of dehydroepiandrosterone in physiology, pathology and therapy]. Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego 24, Pubmed: 18634257
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)
External Links:
ResourceLink
METABOLIGHTSMTBLC28689
HMDBHMDB00077
LIPID_MAPSLMST02020021
DRUGBANKDB01708
CHEMSPIDER5670
CHEBI28689
PUBCHEM5881
CAS53-43-0
LIGAND-CPDC01227
NCI9896