You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-08-13 13:06:47 UTC
Update Date2016-02-11 01:06:35 UTC
HMDB IDHMDB04148
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
3-Hydroxytyramine-4-O-sulfateHMDB
3-Hydroxytyramine-4-O-sulphateHMDB
Dopamine 4-O-sulfateHMDB
Dopamine 4-O-sulphateHMDB
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 KeyInChIKey=DEKNNWJXAQTLFA-UHFFFAOYSA-N
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
Substituents
  • 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 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 Point265 - 270.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.76 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.24 m3·mol-1ChemAxon
Polarizability21.59 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 Quantified0.0027 +/- 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
DrugBank Metabolite IDDBMET00565
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023320
KNApSAcK IDNot Available
Chemspider ID110461
KEGG Compound IDC13691
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04148
Metagene LinkHMDB04148
METLIN IDNot Available
PubChem Compound123932
PDB IDNot Available
ChEBI IDNot Available
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. [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