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Showing Compound DHEA sulfate (FDB022381)

Record Information
Version1.0
Creation date2011-09-21 00:13:08 UTC
Update date2015-07-21 06:57:10 UTC
Primary IDFDB022381
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDHEA sulfate
DescriptionDHEAS or Dehydroepiandrosterone sulfate is the sulfated form of DHEA. This sulfation is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestine. In the blood, most DHEA is found as DHEAS with levels that are about 300 times higher than those of free DHEA. Orally-ingested DHEA is converted to its sulfate when passing through intestines and liver. Whereas DHEA levels naturally reach their peak in the early morning hours, DHEAS levels show no diurnal variation. From a practical point of view, measurement of DHEAS is preferable to DHEA, as levels are more stable. DHEA (from which DHEAS comes from) is a natural steroid prohormone produced from cholesterol by the adrenal glands, the gonads, adipose tissue, brain and in the skin (by an autocrine mechanism). DHEA is the precursor of androstenedione, which can undergo further conversion to produce the androgen testosterone and the estrogens estrone and estradiol. DHEA is also a potent sigma-1 agonist. DHEAS can serve as a precursor for testosterone; androstenedione; estradiol; and estrone. [HMDB]
CAS Number651-48-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3-beta)-3-(Sulfooxy)androst-5-en-17-oneChEBI
17-Ketoandrost-5-en-3beta-yl sulfateChEBI
17-Oxoandrost-5-en-3beta-yl hydrogen sulphateChEBI
3-O-SulfodehydroepiandrosteroneChEBI
3beta-Hydroxyandrost-5-en-17-one 3-sulfateChEBI
Androst-5-en-17-on-3beta-yl sulfuric acidChEBI
Dehydroepiandrosterone 3-sulfateChEBI
Dehydroepiandrosterone monosulfateChEBI
Dehydroepiandrosterone sulphateChEBI
Dehydroisoandrosterone sulfateChEBI
Dehydroisoandrosterone-3-sulfateChEBI
DHEA sulfateChEBI
DHEA-SChEBI
DHEASChEBI
Prasterone sulfateChEBI
(3-b)-3-(Sulfooxy)androst-5-en-17-oneGenerator
(3-b)-3-(Sulphooxy)androst-5-en-17-oneGenerator
(3-beta)-3-(Sulphooxy)androst-5-en-17-oneGenerator
(3-Β)-3-(sulfooxy)androst-5-en-17-oneGenerator
(3-Β)-3-(sulphooxy)androst-5-en-17-oneGenerator
17-Ketoandrost-5-en-3b-yl sulfateGenerator
17-Ketoandrost-5-en-3b-yl sulfuric acidGenerator
17-Ketoandrost-5-en-3b-yl sulphateGenerator
17-Ketoandrost-5-en-3b-yl sulphuric acidGenerator
17-Ketoandrost-5-en-3beta-yl sulfuric acidGenerator
17-Ketoandrost-5-en-3beta-yl sulphateGenerator
17-Ketoandrost-5-en-3beta-yl sulphuric acidGenerator
17-Ketoandrost-5-en-3β-yl sulfateGenerator
17-Ketoandrost-5-en-3β-yl sulfuric acidGenerator
17-Ketoandrost-5-en-3β-yl sulphateGenerator
17-Ketoandrost-5-en-3β-yl sulphuric acidGenerator
17-Oxoandrost-5-en-3b-yl hydrogen sulfateGenerator
17-Oxoandrost-5-en-3b-yl hydrogen sulfuric acidGenerator
17-Oxoandrost-5-en-3b-yl hydrogen sulphateGenerator
17-Oxoandrost-5-en-3b-yl hydrogen sulphuric acidGenerator
17-Oxoandrost-5-en-3beta-yl hydrogen sulfateGenerator
17-Oxoandrost-5-en-3beta-yl hydrogen sulfuric acidGenerator
17-Oxoandrost-5-en-3beta-yl hydrogen sulphuric acidGenerator
17-Oxoandrost-5-en-3β-yl hydrogen sulfateGenerator
17-Oxoandrost-5-en-3β-yl hydrogen sulfuric acidGenerator
17-Oxoandrost-5-en-3β-yl hydrogen sulphateGenerator
17-Oxoandrost-5-en-3β-yl hydrogen sulphuric acidGenerator
3-O-SulphodehydroepiandrosteroneGenerator
3b-Hydroxyandrost-5-en-17-one 3-sulfateGenerator
3b-Hydroxyandrost-5-en-17-one 3-sulfuric acidGenerator
3b-Hydroxyandrost-5-en-17-one 3-sulphateGenerator
3b-Hydroxyandrost-5-en-17-one 3-sulphuric acidGenerator
3beta-Hydroxyandrost-5-en-17-one 3-sulfuric acidGenerator
3beta-Hydroxyandrost-5-en-17-one 3-sulphateGenerator
3beta-Hydroxyandrost-5-en-17-one 3-sulphuric acidGenerator
3Β-hydroxyandrost-5-en-17-one 3-sulfateGenerator
3Β-hydroxyandrost-5-en-17-one 3-sulfuric acidGenerator
3Β-hydroxyandrost-5-en-17-one 3-sulphateGenerator
3Β-hydroxyandrost-5-en-17-one 3-sulphuric acidGenerator
Androst-5-en-17-on-3b-yl sulfateGenerator
Androst-5-en-17-on-3b-yl sulfuric acidGenerator
Androst-5-en-17-on-3b-yl sulphateGenerator
Androst-5-en-17-on-3b-yl sulphuric acidGenerator
Androst-5-en-17-on-3beta-yl sulfateGenerator
Androst-5-en-17-on-3beta-yl sulphateGenerator
Androst-5-en-17-on-3beta-yl sulphuric acidGenerator
Androst-5-en-17-on-3β-yl sulfateGenerator
Androst-5-en-17-on-3β-yl sulfuric acidGenerator
Androst-5-en-17-on-3β-yl sulphateGenerator
Androst-5-en-17-on-3β-yl sulphuric acidGenerator
Dehydroepiandrosterone 3-sulfuric acidGenerator
Dehydroepiandrosterone 3-sulphateGenerator
Dehydroepiandrosterone 3-sulphuric acidGenerator
Dehydroepiandrosterone monosulfuric acidGenerator
Dehydroepiandrosterone monosulphateGenerator
Dehydroepiandrosterone monosulphuric acidGenerator
Dehydroepiandrosterone sulfuric acidGenerator
Dehydroepiandrosterone sulphuric acidGenerator
Dehydroisoandrosterone sulfuric acidGenerator
Dehydroisoandrosterone sulphateGenerator
Dehydroisoandrosterone sulphuric acidGenerator
Dehydroisoandrosterone-3-sulfuric acidGenerator
Dehydroisoandrosterone-3-sulphateGenerator
Dehydroisoandrosterone-3-sulphuric acidGenerator
DHEA sulfuric acidGenerator
DHEA sulphateGenerator
DHEA sulphuric acidGenerator
Prasterone sulfuric acidGenerator
Prasterone sulphateGenerator
Prasterone sulphuric acidGenerator
(3beta)-3-(Sulfooxy)-androst-5-en-17-oneHMDB
17-Oxoandrost-5-en-3-yl hydrogen sulfateHMDB
17-Oxoandrost-5-en-3-yl hydrogen sulphateHMDB
3-b-Hydroxyandrost-5-en-17-one 3-sulfateHMDB
3-b-Hydroxyandrost-5-en-17-one 3-sulphateHMDB
3-beta-Hydroxyandrost-5-en-17-one 3-sulfateHMDB
3-beta-Hydroxyandrost-5-en-17-one 3-sulphateHMDB
3b-Hydroxy-androst-5-en-17-one hydrogen sulfateHMDB
3b-Hydroxy-androst-5-en-17-one hydrogen sulphateHMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulfateHMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulphateHMDB
Dehydroepiandrosterone-3-sulfateHMDB
Dehydroepiandrosterone-3-sulphateHMDB
Formylisoglutamic acidHMDB
Prasterone-3-sulfateHMDB
Prasterone-3-sulphateHMDB
DHA sulfateHMDB
Sulfate, dehydroisoandrosteroneHMDB
Sulfate, prasteroneHMDB
Sulfate, dheaHMDB
Sulfate, dehydroepiandrosteroneHMDB
Sulfate, dhaHMDB
(3-β)-3-(sulfooxy)androst-5-en-17-oneGenerator
(3-β)-3-(sulphooxy)androst-5-en-17-oneGenerator
(3beta)-3-(sulfooxy)-Androst-5-en-17-onehmdb
17-oxoandrost-5-en-3b-yl hydrogen sulfatehmdb
17-oxoandrost-5-en-3beta-yl hydrogen sulfatehmdb
3-b-hydroxyandrost-5-en-17-one 3-sulfatehmdb
3-beta-hydroxyandrost-5-en-17-one 3-sulfatehmdb
3b-hydroxy-Androst-5-en-17-one hydrogen sulfatehmdb
3b-hydroxyandrost-5-en-17-one 3-sulfatehmdb
3beta-hydroxy-Androst-5-en-17-one hydrogen sulfatehmdb
3beta-hydroxyandrost-5-en-17-one 3-sulfatehmdb
3β-hydroxyandrost-5-en-17-one 3-sulfateGenerator
3β-hydroxyandrost-5-en-17-one 3-sulfuric acidGenerator
3β-hydroxyandrost-5-en-17-one 3-sulphateGenerator
3β-hydroxyandrost-5-en-17-one 3-sulphuric acidGenerator
Dehydroepiandrosterone sulfateChEBI
Predicted Properties
PropertyValueSource
Water Solubility0.0081 g/LALOGPS
logP0.49ALOGPS
logP3.42ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.65 m³·mol⁻¹ChemAxon
Polarizability39.85 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H28O5S
IUPAC name[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid
InChI IdentifierInChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1
InChI KeyCZWCKYRVOZZJNM-USOAJAOKSA-N
Isomeric SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O
Average Molecular Weight368.488
Monoisotopic Molecular Weight368.165744696
Classification
Description Belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSulfated steroids
Direct ParentSulfated steroids
Alternative Parents
Substituents
  • Sulfated steroid skeleton
  • Androstane-skeleton
  • 17-oxosteroid
  • Oxosteroid
  • Delta-5-steroid
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfuric acid monoester
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDHEA sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-0097000000-e6d4f60e9803940d2f55Spectrum
Predicted GC-MSDHEA sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-d49a8b7164a230745f202021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-3009000000-bd7e895ed74eba8a0f232021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-8d7ea5bd8a8a0d5219c72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-9001000000-5d89a4081c0f6b0c33242021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0049000000-f9a938b029283c157bdf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0091000000-c2b83d86ae8174524e1d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5792000000-20638b1484fe342eb3c92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-79344bc1ba3ea2c26db72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1092000000-3b129a6c30b2629e16612016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008i-6090000000-35cc27267154382811702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-c58c9c29bacda1fca2402021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1009000000-d5f9b663138c7975150b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9105000000-a5c4a9d21c991c730dab2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-e7315ac14210f0dc39302021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0292000000-06a461930592bd575f192021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-4920000000-e6055497e2f92515f76a2021-09-23View Spectrum
NMRNot Available
ChemSpider ID12074
ChEMBL IDCHEMBL259898
KEGG Compound IDC04555
Pubchem Compound ID12594
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB05804
HMDB IDHMDB01032
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID44038
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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference