Record Information
Version1.0
Creation date2011-04-11 17:01:40 UTC
Update date2019-11-26 03:20:53 UTC
Primary IDFDB021808
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 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. [HMDB]. Dehydroepiandrosterone is found in many foods, some of which are summer grape, quinoa, calabash, and chinese chives.
CAS Number53-43-0
Structure
Thumb
Synonyms
SynonymSource
(+)-DehydroisoandrosteroneHMDB
(3-beta)-3-Hydroxyandrost-5-en-17-oneHMDB
(3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-oneHMDB
(3beta)-3-Hydroxy-androst-5-en-17-oneHMDB
17-ChetovisHMDB
17-HormoforinHMDB
3-beta-Hydroxy-5-androsten-17-oneHMDB
3-beta-Hydroxyandrost-5-en-17-oneHMDB
3b-Hydroxy-D5-androsten-17-oneHMDB
3b-Hydroxyandrost-5-en-17-oneHMDB
3beta-Hydroxy-5-androsten-17-oneHMDB
3beta-Hydroxy-androst-5-en-17-oneHMDB
3beta-Hydroxy-D5-androsten-17-oneHMDB
3beta-Hydroxyandrost-5-en-17-oneHMDB
5-Androsten-3-beta-ol-17-oneHMDB
5-Androsten-3b-ol-17-oneHMDB
5-Androsten-3beta-ol-17-oneHMDB
5-dehydro-EpiandrosteroneHMDB
5-DehydroepiandrosteroneHMDB
5,6-DehydroisoandrosteroneHMDB
5,6-DidehydroisoandrosteroneHMDB
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
DehydroisoandrosteroneHMDB
DiandronHMDB
DiandroneHMDB
HydroxyandrostenoneHMDB
PrasteronaHMDB
PrasteroneHMDB
PrasteronumHMDB
PrestaraHMDB
PsicosteroneHMDB
trans-DehydroandrosteroneHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
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
Polarizability34.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H28O2
IUPAC name5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
InChI IdentifierInChI=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
InChI KeyFMGSKLZLMKYGDP-UHFFFAOYSA-N
Isomeric SMILESCC12CCC3C(CC=C4CC(O)CCC34C)C1CCC2=O
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
Classification
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
  • 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0190000000-ef1bdbe2e566bf990398Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0390000000-bdd35ddc0b6e3286c3c6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-5890000000-c154acb416fe7f522282Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-fd66c37dc9b26db39c67Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-a24aadd604a9c752ac7dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-1190000000-193d5d733f56150dc428Spectrum
NMRNot Available
ChemSpider ID8036443
ChEMBL IDCHEMBL309821
KEGG Compound IDC01227
Pubchem Compound ID9860744
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00077
CRC / DFC (Dictionary of Food Compounds) IDHDV68-S:HGC81-V
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID37131
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Sulfotransferase family cytosolic 2B member 1SULT2B1O00204
Pathways
NameSMPDB LinkKEGG Link
Androgen and Estrogen MetabolismSMP00068 map00150
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference