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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 13:06:47 UTC
Update Date2019-01-11 19:17:56 UTC
HMDB IDHMDB0004148
Secondary Accession Numbers
  • HMDB04148
Metabolite Identification
Common NameDopamine 4-sulfate
DescriptionDopamine 4-sulfate is one of the metabolic products of the endogenous catecholamine dopamine which have also been implicated as intermediate in noradrenaline biosynthesis. In human blood circulation endogenous dopamine exists predominantly in the sulfated form and dopamine sulfate accounts for more than 90% of all dopamine. Sulfonation is the most important metabolic pathway that interferes with the binding of dopamine to its receptors. Dopamine-4-O-sulfate has concentrations about a 10th of those of the regioisomer dopamine-3-O-sulfate. 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 2.8.2.1) 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 ).
Structure
Data?1547234276
Synonyms
ValueSource
3-Hydroxytyramine-4-O-sulfateChEBI
3-Hydroxytyramine-4-O-sulphateChEBI
4-(2-Aminoethyl)-1,2-benzenediol 1-(hydrogen sulfate)ChEBI
[4-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulfonic acidChEBI
Dopamine 4-monosulfateChEBI
Dopamine 4-O-sulphateChEBI
Dopamine 4-sulfateChEBI
3-Hydroxytyramine-4-O-sulfuric acidGenerator
3-Hydroxytyramine-4-O-sulphuric acidGenerator
4-(2-Aminoethyl)-1,2-benzenediol 1-(hydrogen sulfuric acid)Generator
4-(2-Aminoethyl)-1,2-benzenediol 1-(hydrogen sulphate)Generator
4-(2-Aminoethyl)-1,2-benzenediol 1-(hydrogen sulphuric acid)Generator
[4-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulfonateGenerator
[4-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulphonateGenerator
[4-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulphonic acidGenerator
Dopamine 4-monosulfuric acidGenerator
Dopamine 4-monosulphateGenerator
Dopamine 4-monosulphuric acidGenerator
Dopamine 4-O-sulfuric acidGenerator
Dopamine 4-O-sulphuric acidGenerator
Dopamine 4-sulfuric acidGenerator
Dopamine 4-sulphateGenerator
Dopamine 4-sulphuric acidGenerator
Dopamine 4-O-sulfateHMDB
Chemical FormulaC8H11NO5S
Average Molecular Weight233.242
Monoisotopic Molecular Weight233.035793157
IUPAC Name[4-(2-aminoethyl)-2-hydroxyphenyl]oxidanesulfonic acid
Traditional Namedopamine 4-O-sulfate
CAS Registry Number38339-02-5
SMILES
NCCC1=CC=C(OS(O)(=O)=O)C(O)=C1
InChI Identifier
InChI=1S/C8H11NO5S/c9-4-3-6-1-2-8(7(10)5-6)14-15(11,12)13/h1-2,5,10H,3-4,9H2,(H,11,12,13)
InChI KeyDEKNNWJXAQTLFA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassArylsulfates
Direct ParentPhenylsulfates
Alternative Parents
Substituents
  • Phenylsulfate
  • Phenethylamine
  • Phenoxy compound
  • 2-arylethylamine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Benzenoid
  • Primary amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Amine
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point265 - 270.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.76 g/LALOGPS
logP-1.2ALOGPS
logP-0.054ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)9.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.85 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.24 m³·mol⁻¹ChemAxon
Polarizability21.59 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9640000000-1b7fc3a7c37ad38d60c9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0089-8190000000-a63f7b3ef089830280b5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0190000000-73289d25e4e81f1b6ed4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-1950000000-98b6fd0f26a4b893956bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v03-9300000000-b10c4dac22ab4bc8123aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-1438103684ac3976060cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1930000000-4b0cf6044b09ae5876b6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f8i-5900000000-9074ff50da31657737a1JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0027 +/- 0.0003 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.025 +/- 0.004 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023320
KNApSAcK IDNot Available
Chemspider ID110461
KEGG Compound IDC13691
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound123932
PDB IDNot Available
ChEBI ID34729
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. 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. [PubMed:17548063 ]

Enzymes

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:
SULT1A3
Uniprot ID:
P50224
Molecular weight:
34195.96