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Record Information
Version3.6
Creation Date2006-05-22 14:17:34 UTC
Update Date2017-08-16 03:52:53 UTC
HMDB IDHMDB0002062
Secondary Accession Numbers
  • HMDB02062
  • HMDB06346
Metabolite Identification
Common NameNorepinephrine sulfate
DescriptionPlasma norepinephrine sulfate increases after sympathetic nervous system activation by an exhausting incremental exercise test and remain elevated up to 2 h after exercise. (PMID: 8330610 ). Human platelets contribute to the formation of plasma norepinephrine sulfate by norepinephrine uptake, intraplatelet sulfoconjugation and release of norepinephrine sulfate. (PMID: 7968241 ). Higher concentrations of norepinephrine sulfate in portal venous than arterial plasma indicate substantial production of norepinephrine by mesenteric organs. (PMID: 8627312 ). Intravenously infused norepinephrine is sulfoconjugated in humans, indicating that a major part of NE is sulfoconjugated in blood or at sites easily accessible from blood. (PMID: 12020748 ).
Structure
Thumb
Synonyms
ValueSource
Noradrenaline sulfateHMDB
Noradrenaline sulfoconjugateHMDB
Noradrenaline sulphateHMDB
Norepinephrine-3-O-sulfateHMDB
Norepinephrine-3-O-sulphateHMDB
Norepinephrine-O-sulfateHMDB
Norepinephrine-O-sulphateHMDB
Chemical FormulaC8H11NO6S
Average Molecular Weight249.241
Monoisotopic Molecular Weight249.030707779
IUPAC Name{4-[(1R)-2-amino-1-hydroxyethyl]-2-hydroxyphenyl}oxidanesulfonic acid
Traditional Namenorepinephrine sulfate
CAS Registry Number77469-51-3
SMILES
NC[C@H](O)C1=CC(O)=C(OS(O)(=O)=O)C=C1
InChI Identifier
InChI=1S/C8H11NO6S/c9-4-7(11)5-1-2-8(6(10)3-5)15-16(12,13)14/h1-3,7,10-11H,4,9H2,(H,12,13,14)/t7-/m0/s1
InChI KeyCVJMZWLHUCMEKO-ZETCQYMHSA-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
  • Sulfuric acid monoester
  • Sulfate-ester
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility5.97 mg/mLALOGPS
logP-1.6ALOGPS
logP-0.97ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)-2.2ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area130.08 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.45 m3·mol-1ChemAxon
Polarizability22.16 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.007 +/- 0.001 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.009 +/- 0.0008 uMAdult (>18 years old)BothNormal details
UrineExpected but not Quantified Not AvailableNot AvailableNormal
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00549
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022825
    KNApSAcK IDNot Available
    Chemspider ID110309
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0002062
    METLIN IDNot Available
    PubChem Compound123747
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceNot Available
    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. Strobel G, Hack V, Kinscherf R, Weicker H: Sustained noradrenaline sulphate response in long-distance runners and untrained subjects up to 2 h after exhausting exercise. Eur J Appl Physiol Occup Physiol. 1993;66(5):421-6. [PubMed:8330610 ]
    3. Eisenhofer G, Aneman A, Hooper D, Rundqvist B, Friberg P: Mesenteric organ production, hepatic metabolism, and renal elimination of norepinephrine and its metabolites in humans. J Neurochem. 1996 Apr;66(4):1565-73. [PubMed:8627312 ]
    4. Mielke K, Strobel G: The potential of intact human platelets for sulfoconjugation of norepinephrine in vitro. Life Sci. 1994;55(21):1657-63. [PubMed:7968241 ]
    5. Strobel G, Haussmann R, Bartsch P: Effect of differently induced plasma norepinephrine increments on norepinephrine sulfate formation. Life Sci. 2002 May 24;71(1):55-65. [PubMed:12020748 ]