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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-22 20:54:05 UTC
Update Date2020-11-09 23:17:54 UTC
HMDB IDHMDB0006275
Secondary Accession Numbers
  • HMDB06275
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 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?1582752378
Synonyms
ValueSource
4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulfate)ChEBI
[5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulfonic acidChEBI
Dopamine 3-monosulfateChEBI
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
[5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulfonateGenerator
[5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulphonateGenerator
[5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulphonic acidGenerator
Dopamine 3-monosulfuric acidGenerator
Dopamine 3-monosulphateGenerator
Dopamine 3-monosulphuric acidGenerator
Dopamine 3-sulfuric acidGenerator
Dopamine 3-sulphateGenerator
Dopamine 3-sulphuric acidGenerator
Dopamine 3-O-sulfuric acidGenerator
Dopamine 3-O-sulphateGenerator
Dopamine 3-O-sulphuric acidGenerator
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
SMILES
NCCC1=CC(OS(O)(=O)=O)=C(O)C=C1
InChI Identifier
InChI=1S/C8H11NO5S/c9-4-3-6-1-2-7(10)8(5-6)14-15(11,12)13/h1-2,5,10H,3-4,9H2,(H,11,12,13)
InChI KeyNZKRYJGNYPYXJZ-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-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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point268 - 270 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.06 g/LALOGPS
logP10(-1.2) g/LALOGPS
logP10(-0.054) g/LChemAxon
logS10(-1.8) g/LALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.85 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.24 m³·mol⁻¹ChemAxon
Polarizability21.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.41731661259
DarkChem[M-H]-147.98731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dopamine 3-O-sulfate,1TMS,#1C[Si](C)(C)OC1=CC=C(CCN)C=C1OS(=O)(=O)O2140.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dopamine 3-O-sulfate,1TMS,#2C[Si](C)(C)OS(=O)(=O)OC1=CC(CCN)=CC=C1O2084.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dopamine 3-O-sulfate,1TMS,#3C[Si](C)(C)NCCC1=CC=C(O)C(OS(=O)(=O)O)=C12240.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dopamine 3-O-sulfate,1TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC=C(CCN)C=C1OS(=O)(=O)O2379.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dopamine 3-O-sulfate,1TBDMS,#2CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(CCN)=CC=C1O2325.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Dopamine 3-O-sulfate,1TBDMS,#3CC(C)(C)[Si](C)(C)NCCC1=CC=C(O)C(OS(=O)(=O)O)=C12497.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dopamine 3-O-sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9650000000-2db72db7d63697e55bd12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dopamine 3-O-sulfate GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-9320000000-ace4fcc9cdb2373f726c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dopamine 3-O-sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 10V, Positive-QTOFsplash10-0159-0090000000-b2228f1210694d4037be2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 20V, Positive-QTOFsplash10-014r-1950000000-c9ce0c682709c1c90e1d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 40V, Positive-QTOFsplash10-0gdi-9300000000-f413b35bca5b45692bb02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 10V, Negative-QTOFsplash10-001i-0090000000-c18c16811fdd8fb7e8d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 20V, Negative-QTOFsplash10-0udi-1930000000-37551dd11cac8f51977a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 40V, Negative-QTOFsplash10-0f8i-5900000000-6729c4999d2afb12eec02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 10V, Negative-QTOFsplash10-001i-0090000000-b5c60a607f4b8ffe83092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 20V, Negative-QTOFsplash10-001j-5090000000-6dc0ebdf64e66d55361a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 40V, Negative-QTOFsplash10-01ow-9100000000-c48fe767b4f0b00bc40e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 10V, Positive-QTOFsplash10-000i-0920000000-5bc862fdad49e730b60a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 20V, Positive-QTOFsplash10-000i-0900000000-751f9057ce9f08d810362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 40V, Positive-QTOFsplash10-066u-5900000000-9d59879b17c28b88d4642021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0265 +/- 0.011 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
Phenol Explorer Compound IDNot Available
FooDB IDFDB023872
KNApSAcK IDNot Available
Chemspider ID108936
KEGG Compound IDC13690
BioCyc IDCPD-7649
BiGG ID2320809
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound122136
PDB IDNot Available
ChEBI ID37946
Food Biomarker OntologyNot Available
VMH IDDOPASF
MarkerDB IDNot Available
Good Scents IDNot Available
References
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. [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