Showing metabocard for Estrone sulfate (BMDB0001425)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:45:47 UTC
Update Date2020-06-04 18:59:39 UTC
BMDB IDBMDB0001425
Secondary Accession Numbers
  • BMDB01425
Metabolite Identification
Common NameEstrone sulfate
DescriptionEstrone sulfate, also known as evex or conestoral, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Estrone sulfate exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Estrone sulfate exists in all living organisms, ranging from bacteria to humans. Estrone sulfate and adenosine 3',5'-diphosphate can be biosynthesized from estrone and phosphoadenosine phosphosulfate through its interaction with the enzyme estrogen sulfotransferase. In cattle, estrone sulfate is involved in the metabolic pathway called the estrone metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulphateChEBI
Estrone hydrogen sulfateChEBI
Estrone sulphateChEBI
3-Hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulfateGenerator
3-Hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulfuric acidGenerator
3-Hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulphuric acidGenerator
Estrone hydrogen sulfuric acidGenerator
Estrone hydrogen sulphateGenerator
Estrone hydrogen sulphuric acidGenerator
Estrone sulfuric acidGenerator
Estrone sulphuric acidGenerator
ConestoralHMDB
Estrogenic substancesHMDB
EstroneHMDB
Estrone hydrogen sulfateHMDB
Estrone hydrogen sulphateHMDB
Estrone 3-sulfateHMDB
Estrone 3-sulphateHMDB
Estrone sulfate sodiumHMDB
Estrone sulphate sodiumHMDB
Estrone-3-sulfateHMDB
Estrone-3-sulphateHMDB
PremarinHMDB
Sodium estrone 3-monosulfateHMDB
Sodium estrone 3-monosulphateHMDB
Sodium estrone 3-sulfateHMDB
Sodium estrone 3-sulphateHMDB
Estrone sulfate, sodium saltHMDB
Potassium estrone sulfateHMDB
Sodium estrone sulfateHMDB
Estrone sulfate, ammonium saltHMDB
Oestrone sulphateHMDB
EvexHMDB
Estrone sulfate, 16-(14)C-labeledHMDB
Estrone sulfate, 14C-labeledHMDB
Estrone sulfate, potassium saltHMDB
Chemical FormulaC18H22O5S
Average Molecular Weight350.429
Monoisotopic Molecular Weight350.118794504
IUPAC Name[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid
Traditional NameOgen
CAS Registry Number481-97-0
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(OS(O)(=O)=O)=C4)[C@@H]1CCC2=O
InChI Identifier
InChI=1S/C18H22O5S/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/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1
InChI KeyJKKFKPJIXZFSSB-CBZIJGRNSA-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
  • 17-oxosteroid
  • Oxosteroid
  • Phenanthrene
  • Arylsulfate
  • Tetralin
  • Benzenoid
  • Sulfuric acid ester
  • Sulfuric acid monoester
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Ketone
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point254.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.29ALOGPS
logP3.83ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)-1.7ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.07 m³·mol⁻¹ChemAxon
Polarizability36.64 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, Positivesplash10-0079-1195000000-45f680d267db2b386dfbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-66837890a45e12ff4df5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ul0-1298000000-be851ade10d052513145View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-5934000000-d4c5c30541fd04c44e38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-45855a16f86d3580ba3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0093000000-18cc1497d0c7397e16afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gc0-5090000000-83bfa06ed14805d78102View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-e8b485c62cd4477fbfc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9003000000-98936cb1b9953748d5a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-7192000000-e9e53d190e852f9b5b1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-d7902d7f420476e65a84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-2189000000-15572bc45f5db3a69da1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gx1-6693000000-29c27e485a34d776e412View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen Locations
  • Epidermis
  • Intestine
  • Kidney
  • Liver
  • Milk
  • Ovary
  • Placenta
  • Platelet
  • Testis
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.000582 +/- 0.000002854 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.000588 +/- 0.00003995 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.000574 +/- 0.00005137 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.000665 +/- 0.0000371 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.000648 +/- 0.000005707 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.000685 +/- 0.00003139 uMNot SpecifiedNot Specified
Normal		 details
OvaryExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Treated with steroids 		details
HMDB IDHMDB0001425
DrugBank IDDB04574
Phenol Explorer Compound IDNot Available
FooDB IDFDB021804
KNApSAcK IDNot Available
Chemspider ID2272513
KEGG Compound IDC02538
BioCyc IDNot Available
BiGG ID40054
Wikipedia LinkEstrone sulfate
METLIN ID3556
PubChem Compound3001028
PDB IDNot Available
ChEBI ID17474
References
Synthesis ReferencePrice, Wm. H. Process for the production of alkali metal estrone sulfate salts. (1959), US Patent 2917522 19591215
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024. Epub 2010 May 25. [PubMed:20541211 ]

Enzymes

Enzyme Details
1. Sulfotransferase 1E1
General function:
Involved in estrone sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone (PubMed:1900200) (By similarity). Is a key enzyme in estrogen homeostasis, the sulfation of estrogens leads to their inactivation. Also sulfates dehydroepiandrosterone (DHEA), pregnenolone, (24S)-hydroxycholesterol and xenobiotic compounds like ethinylestradiol, equalenin, diethyl stilbesterol and 1-naphthol at significantly lower efficiency. Does not sulfonate cortisol, testosterone and dopamine (By similarity).
Gene Name:
SULT1E1
Uniprot ID:
P19217
Molecular weight:
34640.0
Reactions
Estrone + Phosphoadenosine phosphosulfate → Estrone sulfate + Adenosine 3',5'-diphosphatedetails
Enzyme Details
2. 17-beta-hydroxysteroid dehydrogenase type 6
General function:
Lipid transport and metabolism
Specific function:
NAD-dependent oxidoreductase with broad substrate specificity that shows both oxidative and reductive activity (in vitro). Has 17-beta-hydroxysteroid dehydrogenase activity towards various steroids (in vitro). Converts 5-alpha-androstan-3-alpha,17-beta-diol to androsterone and estradiol to estrone (in vitro). Has 3-alpha-hydroxysteroid dehydrogenase activity towards androsterone (in vitro). Has retinol dehydrogenase activity towards all-trans-retinol (in vitro). Can convert androsterone to epi-androsterone. Androsterone is first oxidized to 5-alpha-androstane-3,17-dione and then reduced to epi-andosterone. Can act on both C-19 and C-21 3-alpha-hydroxysteroids (By similarity).
Gene Name:
HSD17B6
Uniprot ID:
Q3T001
Molecular weight:
36198.0
Enzyme Details
3. Very-long-chain 3-oxoacyl-CoA reductase
General function:
Involved in binding
Specific function:
Catalyzes the second of the four reactions of the long-chain fatty acids elongation cycle. This endoplasmic reticulum-bound enzymatic process, allows the addition of two carbons to the chain of long- and very long-chain fatty acids/VLCFAs per cycle. This enzyme has a 3-ketoacyl-CoA reductase activity, reducing 3-ketoacyl-CoA to 3-hydroxyacyl-CoA, within each cycle of fatty acid elongation. Thereby, it may participate in the production of VLCFAs of different chain lengths that are involved in multiple biological processes as precursors of membrane lipids and lipid mediators. May also catalyze the transformation of estrone (E1) into estradiol (E2) and play a role in estrogen formation.
Gene Name:
HSD17B12
Uniprot ID:
Q5E9H7
Molecular weight:
34495.0