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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-02-23 13:59:03 UTC
Update Date2017-12-07 01:46:17 UTC
HMDB IDHMDB0001876
Secondary Accession Numbers
  • HMDB01876
Metabolite Identification
Common NameEpinephrine sulfate
DescriptionEpinephrine sulfate is found in human plasma at different levels. Glucuronidation may be an improtant pathway for catecholammine in man at rest or under sympathetic stimulation.(PMID: 6688268 ).
Structure
Thumb
Synonyms
ValueSource
(R)-4-[1-Hydroxy-2-(methylamino)ethyl]-2-benzenediol mono(hydrogen sulfate) (ester)HMDB
(R)-4-[1-Hydroxy-2-(methylamino)ethyl]-2-benzenediol mono(hydrogen sulphate) (ester)HMDB
Adrenaline sulfateHMDB
Adrenaline sulphateHMDB
Epinephrine sulfoconjugateHMDB
Epinephrine-3-O-sulfateMeSH
Chemical FormulaC9H13NO6S
Average Molecular Weight263.268
Monoisotopic Molecular Weight263.046357843
IUPAC Name{2-hydroxy-4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenyl}oxidanesulfonic acid
Traditional Nameepinephrine sulfoconjugate
CAS Registry Number77469-50-2
SMILES
CNC[C@H](O)C1=CC(O)=C(OS(O)(=O)=O)C=C1
InChI Identifier
InChI=1S/C9H13NO6S/c1-10-5-8(12)6-2-3-9(7(11)4-6)16-17(13,14)15/h2-4,8,10-12H,5H2,1H3,(H,13,14,15)/t8-/m0/s1
InChI KeyAELFRHHZGTVYGJ-QMMMGPOBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylsulfates. These are compounds containing a sulfuric acid group conjugated to a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic sulfuric acids and derivatives
Direct ParentPhenylsulfates
Alternative Parents
Substituents
  • Phenylsulfate
  • Phenoxy compound
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Organic nitrogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.55 g/LALOGPS
logP-1.6ALOGPS
logP-0.75ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)9.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.09 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.22 m³·mol⁻¹ChemAxon
Polarizability24.3 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0006-9220000000-2ece4d03b2567c81287bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01bc-9647000000-df7d020cb12314aed975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0090000000-10698a49856be4dc14e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1690000000-404ceebd15110a71f4dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7p-9530000000-2681df63164cd1374dd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1090000000-c14175b75803b9f650fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-2940000000-cc1a9d9f83dd8f4a2240View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kar-5900000000-42cb1da8290c53d480afView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0057 +/- 0.003 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.004 +/- 0.002 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00537
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022721
KNApSAcK IDNot Available
Chemspider ID2299690
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3035453
PDB IDNot Available
ChEBI ID89878
References
Synthesis ReferenceLernhardt U; Strobel G; Schell H; Werle E; Weicker H Modified syntheses of dopamine-4-sulfate, epinephrine-3-sulfate, and norepinephrine-3-sulfate: determination of the position of the sulfate group by 1H-NMR spectroscopy. International journal of sports medicine (1988), 9 Suppl 2 S89-92.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
  2. Claustre J, Serusclat P, Peyrin L: Glucuronide and sulfate catecholamine conjugates in rat and human plasma. J Neural Transm. 1983;56(4):265-78. [PubMed:6688268 ]