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Showing Compound Dopamine 3-sulfate (FDB023872)

Record Information
Version1.0
Creation date2011-09-21 00:36:07 UTC
Update date2015-07-21 06:57:55 UTC
Primary IDFDB023872
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDopamine 3-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) [HMDB]
CAS Number51317-41-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility4.06 g/LALOGPS
logP-1.2ALOGPS
logP-0.054ChemAxon
logS-1.8ALOGPS
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
Chemical FormulaC8H11NO5S
IUPAC name[5-(2-aminoethyl)-2-hydroxyphenyl]oxidanesulfonic acid
InChI IdentifierInChI=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
Isomeric SMILESNCCC1=CC(OS(O)(=O)=O)=C(O)C=C1
Average Molecular Weight233.242
Monoisotopic Molecular Weight233.035793157
Classification
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

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDopamine 3-sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9650000000-2db72db7d63697e55bd1Spectrum
Predicted GC-MSDopamine 3-sulfate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fl0-9320000000-ace4fcc9cdb2373f726cSpectrum
Predicted GC-MSDopamine 3-sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0090000000-b2228f1210694d4037be2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-1950000000-c9ce0c682709c1c90e1d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdi-9300000000-f413b35bca5b45692bb02016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-c18c16811fdd8fb7e8d72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1930000000-37551dd11cac8f51977a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f8i-5900000000-6729c4999d2afb12eec02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-b5c60a607f4b8ffe83092021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-5090000000-6dc0ebdf64e66d55361a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ow-9100000000-c48fe767b4f0b00bc40e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0920000000-5bc862fdad49e730b60a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-751f9057ce9f08d810362021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-5900000000-9d59879b17c28b88d4642021-09-22View Spectrum
NMRNot Available
ChemSpider ID108936
ChEMBL IDNot Available
KEGG Compound IDC13690
Pubchem Compound ID122136
Pubchem Substance IDNot Available
ChEBI ID37946
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06275
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2320809
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference