Showing metabocard for DHEA sulfate (BMDB0001032)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:08 UTC
Update Date2020-05-21 16:29:05 UTC
BMDB IDBMDB0001032
Secondary Accession Numbers
  • BMDB01032
Metabolite Identification
Common NameDHEA sulfate
DescriptionDehydroepiandrosterone sulfate, also known as Dehydroepiandrosterone sulfate or dehydroepiandrosterone sulfate, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Dehydroepiandrosterone sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dehydroepiandrosterone sulfate participates in a number of enzymatic reactions, within cattle. In particular, Adenosine 3',5'-diphosphate and dehydroepiandrosterone sulfate can be biosynthesized from phosphoadenosine phosphosulfate and dehydroepiandrosterone through the action of the enzyme sulfotransferase family cytosolic 2B member 1. In addition, Dehydroepiandrosterone sulfate can be converted into dehydroepiandrosterone and sulfate through the action of the enzyme steryl-sulfatase. In cattle, dehydroepiandrosterone sulfate is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Dehydroepiandrosterone sulfate is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC19H28O5S
Average Molecular Weight368.488
Monoisotopic Molecular Weight368.165744696
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
Traditional 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
CAS Registry Number651-48-9
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
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-0097000000-e6d4f60e9803940d2f55View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-d49a8b7164a230745f20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-3009000000-bd7e895ed74eba8a0f23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-8d7ea5bd8a8a0d5219c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-9001000000-5d89a4081c0f6b0c3324View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0049000000-f9a938b029283c157bdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0091000000-c2b83d86ae8174524e1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5792000000-20638b1484fe342eb3c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-79344bc1ba3ea2c26db7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1092000000-3b129a6c30b2629e1661View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008i-6090000000-35cc2726715438281170View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-c58c9c29bacda1fca240View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1009000000-d5f9b663138c7975150bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9105000000-a5c4a9d21c991c730dabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-e7315ac14210f0dc3930View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0292000000-06a461930592bd575f19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-4920000000-e6055497e2f92515f76aView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Kidney
  • Liver
  • Placenta
  • Prostate Tissue
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Treated with steroids 		details
HMDB IDHMDB0001032
DrugBank IDDB05804
Phenol Explorer Compound IDNot Available
FooDB IDFDB022381
KNApSAcK IDNot Available
Chemspider ID12074
KEGG Compound IDC04555
BioCyc IDDEHYDRO-EPIANDROSTERONE-SULFATE
BiGG ID44038
Wikipedia LinkDehydroepiandrosterone_sulfate
METLIN ID4095
PubChem Compound12594
PDB IDNot Available
ChEBI ID16814
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Arylsulfatase A
General function:
Inorganic ion transport and metabolism
Specific function:
Hydrolyzes cerebroside sulfate.
Gene Name:
ARSA
Uniprot ID:
Q08DD1
Molecular weight:
53807.0
Reactions
DHEA sulfate + Water → Dehydroepiandrosterone + Sulfatedetails
Enzyme Details
2. Sulfotransferase 1A1
General function:
Involved in aryl sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk (By similarity).
Gene Name:
SULT1A1
Uniprot ID:
P50227
Molecular weight:
34184.0
Reactions
Phosphoadenosine phosphosulfate + Dehydroepiandrosterone → Adenosine 3',5'-diphosphate + DHEA sulfatedetails