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Record Information
Creation Date2007-05-22 20:54:05 UTC
Update Date2016-02-11 01:07:27 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameDopamine 3-O-sulfate
DescriptionDopamine 3-O-sulfate is a sulfonated form of dopamine. In human blood circulation endogenous dopamine exists predominantly in the sulfated form and dopamine sulfate accounts for more than 90% of all dopamine. Dopamine-3-O-sulfate predominates in human plasma, with concentrations about 10-fold higher than those of the regioisomer dopamine-4-O-sulfate. Sulfonation is the most important metabolic pathway that interferes with the binding of dopamine to its receptors. The origins of this preponderance for Dopamine-3-O-sulfate have not been determined, although there has been speculation about the contribution of the specificity of transport proteins and/or arylsulfatases. It has also been proposed to depend on the regiospecificity of the metabolizing enzyme(s) for the 3-hydroxy group of dopamine. It is believed that the vast majority of circulating dopamine sulfate originates in the upper gastrointestinal tract, and indeed that is the main site of expression of the enzyme responsible for its formation. Aryl sulfotransferase (SULT1A3, EC is an enzyme that catalyzes the sulfonation of many endogenous and exogenous phenols and catechols; the most important endogenous substrate is dopamine. SULT1A3 strongly favors the 3-hydroxy group of dopamine over the 4-hydroxy group and may indeed be primarily responsible for the difference between the circulating levels of dopamine sulfates in human blood. (PMID: 17548063 ).
4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulfate)ChEBI
Dopamine 3-sulfateChEBI
4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulfuric acid)Generator
4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulphate)Generator
4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulphuric acid)Generator
Chemical FormulaC8H11NO5S
Average Molecular Weight233.242
Monoisotopic Molecular Weight233.035793157
IUPAC Name[5-(2-aminoethyl)-2-hydroxyphenyl]oxidanesulfonic acid
Traditional Namedopamine 3-O-sulfate
CAS Registry Number51317-41-0
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylsulfates. These are compounds containing a sulfuric acid group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylsulfates
Direct ParentPhenylsulfates
Alternative Parents
  • Phenylsulfate
  • Phenethylamine
  • Aralkylamine
  • Sulfuric acid monoester
  • Phenol
  • Sulfuric acid ester
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
StatusDetected and Quantified
  • Drug metabolite
  • Endogenous
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
Experimental Properties
Melting Point268 - 270 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility4.06 mg/mLALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.85 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.24 m3·mol-1ChemAxon
Polarizability21.2 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified0.0265 +/- 0.011 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.16 +/- 0.05 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 IDDBMET00573
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023872
KNApSAcK IDNot Available
Chemspider ID108936
KEGG Compound IDC13690
BioCyc IDCPD-7649
BiGG ID2320809
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06275
Metagene LinkHMDB06275
METLIN IDNot Available
PubChem Compound122136
PDB IDNot Available
ChEBI ID37946
Synthesis ReferenceOsikowska, Barbara A.; Idle, J. R.; Swinbourne, F. J.; Sever, P. S. Unequivocal synthesis and characterization of dopamine 3- and 4-O-sulfates. Biochemical Pharmacology (1982), 31(13), 2279-84.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Itaaho K, Alakurtti S, Yli-Kauhaluoma J, Taskinen J, Coughtrie MW, Kostiainen R: Regioselective sulfonation of dopamine by SULT1A3 in vitro provides a molecular explanation for the preponderance of dopamine-3-O-sulfate in human blood circulation. Biochem Pharmacol. 2007 Aug 1;74(3):504-10. Epub 2007 May 10. [17548063 ]


General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
Uniprot ID:
Molecular weight: