NP-MRD: Showing NP-Card for Dopamine 3-sulfate (NP0087479)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 16:50:48 UTC

Updated at

2022-05-11 16:50:48 UTC

NP-MRD ID

NP0087479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dopamine 3-sulfate

Description

Dopamine 3-O-sulfate, also known as dopamine 3-monosulphate, belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. Dopamine 3-sulfate was first documented in 1975 (PMID: 1195131). Dopamine 3-O-sulfate is a very strong basic compound (based on its pKa) (PMID: 571950) (PMID: 6496664) (PMID: 938583).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652312191915362D          

 15 15  0  0  0  0            999 V2000
    5.9011   -5.8886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6157   -5.5277    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.3302   -5.1151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8956   -6.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3358   -4.7836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0447   -6.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7593   -6.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4737   -6.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4737   -5.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7593   -5.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0447   -5.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3302   -6.7651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1883   -5.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9028   -5.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6172   -5.1151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  7  6  1  0  0  0  0
 11  6  2  0  0  0  0
 12  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 13  9  1  0  0  0  0
 11 10  1  0  0  0  0
  3 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087479

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
NZKRYJGNYPYXJZ-UHFFFAOYSA-N

> <FORMULA>
C8H11NO5S

> <MOLECULAR_WEIGHT>
233.242

> <EXACT_MASS>
233.035793157

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.201640694643448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[5-(2-aminoethyl)-2-hydroxyphenyl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-1.22

> <JCHEM_LOGP>
-0.054285728027644746

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.55238694286428

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.065613083530857

> <JCHEM_PKA_STRONGEST_BASIC>
9.69097547001141

> <JCHEM_POLAR_SURFACE_AREA>
109.84999999999998

> <JCHEM_REFRACTIVITY>
53.24000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dopamine 3-O-sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-DEC-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-DEC-19         0                                  
HETATM    1  O   UNK     0      11.015 -10.992   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0      12.349 -10.318   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      13.683  -9.548   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.872 -11.528   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.827  -8.929   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      15.017 -11.858   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.351 -12.628   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.684 -11.858   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.684 -10.318   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.351  -9.548   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.017 -10.318   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.683 -12.628   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.018  -9.548   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.352 -10.318   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      21.685  -9.548   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2   11                                                       
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    7   11   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11    6   10    3                                                  
CONECT   12    6                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulfate)	ChEBI
[5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulfonic acid	ChEBI
Dopamine 3-monosulfate	ChEBI
Dopamine 3-sulfate	ChEBI
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]oxidanesulfonate	Generator
[5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulphonate	Generator
[5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulphonic acid	Generator
Dopamine 3-monosulfuric acid	Generator
Dopamine 3-monosulphate	Generator
Dopamine 3-monosulphuric acid	Generator
Dopamine 3-sulfuric acid	Generator
Dopamine 3-sulphate	Generator
Dopamine 3-sulphuric acid	Generator
Dopamine 3-O-sulfuric acid	Generator
Dopamine 3-O-sulphate	Generator
Dopamine 3-O-sulphuric acid	Generator

Chemical Formula

C₈H₁₁NO₅S

Average Mass

233.2420 Da

Monoisotopic Mass

233.03579 Da

IUPAC Name

[5-(2-aminoethyl)-2-hydroxyphenyl]oxidanesulfonic acid

Traditional Name

dopamine 3-O-sulfate

CAS Registry Number

Not Available

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 Key

NZKRYJGNYPYXJZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Arylsulfates

Direct Parent

Phenylsulfates

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aryl sulfate (CHEBI:37946 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.2	ALOGPS
logP	-0.054	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	-2.1	ChemAxon
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.85 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.24 m³·mol⁻¹	ChemAxon
Polarizability	21.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006275

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023872

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122136

PDB ID

Not Available

ChEBI ID

37946

Good Scents ID

Not Available

References

General References

Bronaugh RL, Hattox SE, Hoehn MM, Murphy RC, Rutledge CO: The separation and identification of dopamine 3-O-sulfate and dopamine 4-O-sulfate in urine of Parkinsonian patients. J Pharmacol Exp Ther. 1975 Dec;195(3):441-52. [PubMed:1195131 ]
Buu NT, Kuchel O: The direct converstion of dopamine 3-O-sulfate to norepinephrine by dopamine-beta-hydroxylase. Life Sci. 1979 Feb 26;24(9):783-9. doi: 10.1016/0024-3205(79)90361-8. [PubMed:571950 ]
Racz K, Buu NT, Kuchel O, De Lean A: Dopamine 3-sulfate inhibits aldosterone secretion in cultured bovine adrenal cells. Am J Physiol. 1984 Oct;247(4 Pt 1):E431-5. doi: 10.1152/ajpendo.1984.247.4.E431. [PubMed:6496664 ]
Merits I: Formation and metabolism of [14C] dopamine 3-O-sulfate in dog, rat and guinea pig. Biochem Pharmacol. 1976 Apr 1;25(7):829-33. doi: 10.1016/0006-2952(76)90154-4. [PubMed:938583 ]

Showing NP-Card for Dopamine 3-sulfate (NP0087479)

MOL for NP0087479 (Dopamine 3-sulfate)

3D MOL for NP0087479 (Dopamine 3-sulfate)

3D SDF for NP0087479 (Dopamine 3-sulfate)

3D-SDF for NP0087479 (Dopamine 3-sulfate)

PDB for NP0087479 (Dopamine 3-sulfate)

3D PDB for NP0087479 (Dopamine 3-sulfate)

SMILES for NP0087479 (Dopamine 3-sulfate)

INCHI for NP0087479 (Dopamine 3-sulfate)

Structure for NP0087479 (Dopamine 3-sulfate)

3D Structure for NP0087479 (Dopamine 3-sulfate)