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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 19:06:21 UTC
Update Date2021-09-14 15:40:24 UTC
HMDB IDHMDB0004448
Secondary Accession Numbers
  • HMDB04448
Metabolite Identification
Common Name17beta-Estradiol 3-sulfate
Description17beta-Estradiol 3-sulfate, also known as estradiol 3-sulfuric acid or estradiol-17beta 3-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. 17beta-Estradiol 3-sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle(Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy.
Structure
Data?1584994261
Synonyms
ValueSource
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfateChEBI
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfateChEBI
Estradiol 3-sulphateChEBI
Estradiol-17beta 3-sulfateChEBI
Estradiol-3-sulfateChEBI
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfateGenerator
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfuric acidGenerator
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphateGenerator
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphuric acidGenerator
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfuric acidGenerator
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphateGenerator
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphuric acidGenerator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfateGenerator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfuric acidGenerator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphateGenerator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphuric acidGenerator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfateGenerator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfuric acidGenerator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphateGenerator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphuric acidGenerator
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfuric acidGenerator
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphateGenerator
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphuric acidGenerator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfateGenerator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfuric acidGenerator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphateGenerator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphuric acidGenerator
Estradiol 3-sulfateGenerator
Estradiol 3-sulfuric acidGenerator
Estradiol 3-sulphuric acidGenerator
Estradiol-17b 3-sulfateGenerator
Estradiol-17b 3-sulfuric acidGenerator
Estradiol-17b 3-sulphateGenerator
Estradiol-17b 3-sulphuric acidGenerator
Estradiol-17beta 3-sulfuric acidGenerator
Estradiol-17beta 3-sulphateGenerator
Estradiol-17beta 3-sulphuric acidGenerator
Estradiol-17β 3-sulfateGenerator
Estradiol-17β 3-sulfuric acidGenerator
Estradiol-17β 3-sulphateGenerator
Estradiol-17β 3-sulphuric acidGenerator
Estradiol-3-sulfuric acidGenerator
Estradiol-3-sulphateGenerator
Estradiol-3-sulphuric acidGenerator
17b-Estradiol 3-sulfateGenerator
17b-Estradiol 3-sulfuric acidGenerator
17b-Estradiol 3-sulphateGenerator
17b-Estradiol 3-sulphuric acidGenerator
17beta-Estradiol 3-sulfuric acidGenerator
17beta-Estradiol 3-sulphateGenerator
17beta-Estradiol 3-sulphuric acidGenerator
17Β-estradiol 3-sulfateGenerator
17Β-estradiol 3-sulfuric acidGenerator
17Β-estradiol 3-sulphateGenerator
17Β-estradiol 3-sulphuric acidGenerator
17beta-Estradiol sulfateHMDB
17beta-Estradiol sulphateHMDB
17Β-estradiol sulfateHMDB
17Β-estradiol sulphateHMDB
17beta-Estradiol 3-sulfateHMDB
Chemical FormulaC18H24O5S
Average Molecular Weight352.45
Monoisotopic Molecular Weight352.134445047
IUPAC Name[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl]oxidanesulfonic acid
Traditional Name[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl]oxidanesulfonic acid
CAS Registry Number481-96-9
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OS(O)(=O)=O)C=C3CC[C@@]21[H]
InChI Identifier
InChI=1S/C18H24O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-17,19H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,17+,18+/m1/s1
InChI KeyQZIGLSSUDXBTLJ-ZBRFXRBCSA-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
  • Estrane-skeleton
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Phenanthrene
  • Arylsulfate
  • Tetralin
  • Benzenoid
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Organic sulfuric acid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.6 mg/L at 27 °CNot Available
LogP2.936Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP0.16ALOGPS
logP1.57ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.9 m³·mol⁻¹ChemAxon
Polarizability37.68 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-223.26730932474
DeepCCS[M+Na]+198.06230932474
AllCCS[M+H]+184.132859911
AllCCS[M+H-H2O]+181.332859911
AllCCS[M+NH4]+186.732859911
AllCCS[M+Na]+187.432859911
AllCCS[M-H]-183.232859911
AllCCS[M+Na-2H]-183.332859911
AllCCS[M+HCOO]-183.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
17beta-Estradiol 3-sulfate[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OS(O)(=O)=O)C=C3CC[C@@]21[H]4650.1Standard polar33892256
17beta-Estradiol 3-sulfate[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OS(O)(=O)=O)C=C3CC[C@@]21[H]2803.4Standard non polar33892256
17beta-Estradiol 3-sulfate[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OS(O)(=O)=O)C=C3CC[C@@]21[H]3096.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
17beta-Estradiol 3-sulfate,1TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(OS(=O)(=O)O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C3178.2Semi standard non polar33892256
17beta-Estradiol 3-sulfate,1TMS,isomer #2C[C@]12CC[C@@H]3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O3123.2Semi standard non polar33892256
17beta-Estradiol 3-sulfate,2TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C3148.3Semi standard non polar33892256
17beta-Estradiol 3-sulfate,2TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C3158.2Standard non polar33892256
17beta-Estradiol 3-sulfate,2TMS,isomer #1C[C@]12CC[C@@H]3C4=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C3727.1Standard polar33892256
17beta-Estradiol 3-sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(OS(=O)(=O)O)=CC=C4[C@H]3CC[C@]12C3474.7Semi standard non polar33892256
17beta-Estradiol 3-sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]123362.6Semi standard non polar33892256
17beta-Estradiol 3-sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C3673.0Semi standard non polar33892256
17beta-Estradiol 3-sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C3705.4Standard non polar33892256
17beta-Estradiol 3-sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C3880.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 17beta-Estradiol 3-sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 10V, Positive-QTOFsplash10-0f79-0019000000-ca9cb18127c021c08b1b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 20V, Positive-QTOFsplash10-052r-0297000000-01f46b2a5b35f2cc509d2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 40V, Positive-QTOFsplash10-002u-3961000000-490f7ea3a427ec2aeee82019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 10V, Negative-QTOFsplash10-0udi-0009000000-0b04c74e16882ade2cae2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 20V, Negative-QTOFsplash10-0uk9-0093000000-0df31e427e4f5bdca8842019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 40V, Negative-QTOFsplash10-0knc-4090000000-1547f1a5a0346810c8292019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 10V, Negative-QTOFsplash10-0udi-0009000000-94abf727a938582892862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 20V, Negative-QTOFsplash10-0udi-1009000000-0d419d0dc3e14754ecc22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 40V, Negative-QTOFsplash10-0002-9015000000-33c33a97f8108eb6169f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 10V, Positive-QTOFsplash10-0udi-0009000000-f5481d1faa140b88ef322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 20V, Positive-QTOFsplash10-0zfr-0269000000-d5fe5f3755fc2f0a06a92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17beta-Estradiol 3-sulfate 40V, Positive-QTOFsplash10-002b-1930000000-99a045d39fd4ca0d3b5e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112363
KNApSAcK IDNot Available
Chemspider ID59790
KEGG Compound IDC08357
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound66416
PDB IDNot Available
ChEBI ID4866
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available