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Record Information
Version1.0
Creation Date2016-07-13 19:40:55 UTC
Update Date2016-09-23 18:44:30 UTC
LmdbLMDB00034
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 animal 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
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 Name(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
Traditional Name(1S,2R,5S,10R,11S,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
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.66 m³·mol⁻¹ChemAxon
Polarizability34.1 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-004i-4920000000-9dc14963a290268534b8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-3910000000-2bbc760dbeb7f9f1ebfcView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0abi-1790000000-52f5e67bc4d1fab73561View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-022a-1229000000-5fc1bd40299ad859ad1cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fk9-0190000000-66ac82624767dc6821e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0w90-1690000000-b3a231fc509b7a34e09cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-08gj-1930000000-309dc082cc36ec9dcd8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-06sj-2910000000-378638f2a861c948f79dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0536-3900000000-72e80e1a07c4d3a40a7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0036-4900000000-26c8272483a80d1b5eabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0290000000-1a3588ca5d5bacb9ad30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0bta-3920000000-2df257db43df6cc86570View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-89da8cb383a0718d9033View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0390000000-e6efd70cef2520255bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udm-4690000000-e304b251e97b02f672adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-89da8cb383a0718d9033View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0390000000-e6efd70cef2520255bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udm-4690000000-e304b251e97b02f672adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-7498c93972acc3c16404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-d3ddffc56e91bed39fc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-2190000000-15aba54ba135047ffe9aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4l-6940000000-948ad487c238d48aa9beView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected and Quantified0.00052 uMNot AvailableBovine details
SerumDetected and Quantified0.00118 uMNot AvailableBovine details
SerumDetected and Quantified<0.000884 uMNot AvailableBovine details
SerumDetected and Quantified<0.000884 uMNot AvailableBovine details
DrugBank IDDB01708
HMDB IDHMDB0000077
FooDB IDFDB021808
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID37131
BioCyc ID3-BETA-HYDROXYANDROST-5-EN-17-ONE
METLIN ID5133
PDB IDNot Available
Wikipedia LinkDehydroepiandrosterone
Chemspider ID8036443
ChEBI ID28689
PubChem Compound ID5881
Kegg Compound IDC01227
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available