Dopamine 3-O-sulfate (CHEM021702)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:25 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021702
Identification
Common NameDopamine 3-O-sulfate
ClassSmall Molecule
DescriptionAn aryl sulfate that is dopamine in which the phenolic hydrogen at position 3 has been replaced by a sulfo group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass233.242 g/mol
Monoisotopic Mass233.036 g/mol
CAS Registry Number51317-41-0
IUPAC Name[5-(2-aminoethyl)-2-hydroxyphenyl]oxidanesulfonic acid
Traditional Namedopamine 3-O-sulfate
SMILESNCCC1=CC(OS(O)(=O)=O)=C(O)C=C1
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9650000000-2db72db7d63697e55bd1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-9320000000-ace4fcc9cdb2373f726cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0090000000-b2228f1210694d4037beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-1950000000-c9ce0c682709c1c90e1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdi-9300000000-f413b35bca5b45692bb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-c18c16811fdd8fb7e8d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1930000000-37551dd11cac8f51977aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f8i-5900000000-6729c4999d2afb12eec0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-b5c60a607f4b8ffe8309Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-5090000000-6dc0ebdf64e66d55361aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ow-9100000000-c48fe767b4f0b00bc40eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0920000000-5bc862fdad49e730b60aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-751f9057ce9f08d81036Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-5900000000-9d59879b17c28b88d464Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006275
FooDB IDFDB023872
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2320809
BioCyc IDCPD-7649
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID108936
ChEBI ID37946
PubChem Compound ID122136
Kegg Compound IDC13690
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1195131
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17548063
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=4055948
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=571950
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6496664
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=938583
7. Osikowska, 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.
8. Osikowska, 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.
9. 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.