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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-05-22 20:54:05 UTC

Update Date

2020-11-09 23:17:54 UTC

HMDB ID

HMDB0006275

Secondary Accession Numbers

HMDB06275

Metabolite Identification

Common Name

Dopamine 3-O-sulfate

Description

Dopamine 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

MOL 3D MOL SDF 3D SDF PDB 3D 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>
HMDB0006275

> <DATABASE_NAME>
hmdb

> <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

COMPND    HMDB0006275
HETATM    1  N1  UNL     1      -4.278  -0.417   1.239  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.010   0.099   0.839  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.232  -0.814  -0.070  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.947  -0.124  -0.386  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.815   0.722  -1.479  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.376   1.353  -1.761  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.477   1.161  -0.960  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.678   1.817  -1.271  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.376   0.330   0.127  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.476   0.125   0.945  1.00  0.00           O  
HETATM   11  S1  UNL     1       3.605  -1.119   0.681  1.00  0.00           S  
HETATM   12  O3  UNL     1       2.950  -2.380   0.195  1.00  0.00           O  
HETATM   13  O4  UNL     1       4.247  -1.445   2.003  1.00  0.00           O  
HETATM   14  O5  UNL     1       4.820  -0.652  -0.368  1.00  0.00           O  
HETATM   15  C8  UNL     1       0.184  -0.292   0.396  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.395  -1.431   1.173  1.00  0.00           H  
HETATM   17  H2  UNL     1      -5.078   0.163   0.977  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.182   1.067   0.315  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.395   0.289   1.752  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.992  -1.764   0.450  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.825  -0.986  -1.004  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.689   0.865  -2.102  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.432   2.002  -2.622  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.695   2.415  -2.082  1.00  0.00           H  
HETATM   25  H10 UNL     1       5.445  -0.018   0.067  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.077  -0.966   1.267  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3   18   19
CONECT    3    4   20   21
CONECT    4    5    5   15
CONECT    5    6   22
CONECT    6    7    7   23
CONECT    7    8    9
CONECT    8   24
CONECT    9   10   15   15
CONECT   10   11
CONECT   11   12   12   13   13
CONECT   11   14
CONECT   14   25
CONECT   15   26
END

View in JSmol View NMR Assignments View Stereo Labels

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 Molecular Weight

233.242

Monoisotopic Molecular Weight

233.035793157

IUPAC Name

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

Traditional Name

dopamine 3-O-sulfate

CAS Registry Number

51317-41-0

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 Key

NZKRYJGNYPYXJZ-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.

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 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	268 - 270 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.06 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	150.417	31661259
DarkChem	[M-H]-	147.987	31661259
DeepCCS	[M+H]+	154.489	30932474
DeepCCS	[M-H]-	152.131	30932474
DeepCCS	[M-2H]-	185.202	30932474
DeepCCS	[M+Na]+	160.582	30932474
AllCCS	[M+H]+	150.5	32859911
AllCCS	[M+H-H2O]+	146.7	32859911
AllCCS	[M+NH4]+	154.1	32859911
AllCCS	[M+Na]+	155.1	32859911
AllCCS	[M-H]-	145.3	32859911
AllCCS	[M+Na-2H]-	145.8	32859911
AllCCS	[M+HCOO]-	146.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.51 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6884 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.39 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	218.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	508.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	273.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	87.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	263.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	290.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	741.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	653.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	144.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	867.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	169.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	514.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	393.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	272.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dopamine 3-O-sulfate	NCCC1=CC(OS(O)(=O)=O)=C(O)C=C1	3621.9	Standard polar	33892256
Dopamine 3-O-sulfate	NCCC1=CC(OS(O)(=O)=O)=C(O)C=C1	2182.7	Standard non polar	33892256
Dopamine 3-O-sulfate	NCCC1=CC(OS(O)(=O)=O)=C(O)C=C1	2114.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dopamine 3-O-sulfate,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN)C=C1OS(=O)(=O)O	2140.9	Semi standard non polar	33892256
Dopamine 3-O-sulfate,1TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=CC(CCN)=CC=C1O	2084.2	Semi standard non polar	33892256
Dopamine 3-O-sulfate,1TMS,isomer #3	C[Si](C)(C)NCCC1=CC=C(O)C(OS(=O)(=O)O)=C1	2240.6	Semi standard non polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN)C=C1OS(=O)(=O)O[Si](C)(C)C	2134.2	Semi standard non polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN)C=C1OS(=O)(=O)O[Si](C)(C)C	2260.7	Standard non polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN)C=C1OS(=O)(=O)O[Si](C)(C)C	3084.9	Standard polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #2	C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O)=C1	2233.1	Semi standard non polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #2	C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O)=C1	2390.2	Standard non polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #2	C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O)=C1	2963.4	Standard polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #3	C[Si](C)(C)NCCC1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C)=C1	2194.1	Semi standard non polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #3	C[Si](C)(C)NCCC1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C)=C1	2340.5	Standard non polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #3	C[Si](C)(C)NCCC1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C)=C1	3064.4	Standard polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #4	C[Si](C)(C)N(CCC1=CC=C(O)C(OS(=O)(=O)O)=C1)[Si](C)(C)C	2385.4	Semi standard non polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #4	C[Si](C)(C)N(CCC1=CC=C(O)C(OS(=O)(=O)O)=C1)[Si](C)(C)C	2460.7	Standard non polar	33892256
Dopamine 3-O-sulfate,2TMS,isomer #4	C[Si](C)(C)N(CCC1=CC=C(O)C(OS(=O)(=O)O)=C1)[Si](C)(C)C	3307.9	Standard polar	33892256
Dopamine 3-O-sulfate,3TMS,isomer #1	C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)=C1	2219.3	Semi standard non polar	33892256
Dopamine 3-O-sulfate,3TMS,isomer #1	C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)=C1	2440.0	Standard non polar	33892256
Dopamine 3-O-sulfate,3TMS,isomer #1	C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)=C1	2754.5	Standard polar	33892256
Dopamine 3-O-sulfate,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1OS(=O)(=O)O	2387.4	Semi standard non polar	33892256
Dopamine 3-O-sulfate,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1OS(=O)(=O)O	2566.9	Standard non polar	33892256
Dopamine 3-O-sulfate,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1OS(=O)(=O)O	2839.7	Standard polar	33892256
Dopamine 3-O-sulfate,3TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)OC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2353.2	Semi standard non polar	33892256
Dopamine 3-O-sulfate,3TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)OC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2579.0	Standard non polar	33892256
Dopamine 3-O-sulfate,3TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)OC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2946.1	Standard polar	33892256
Dopamine 3-O-sulfate,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1OS(=O)(=O)O[Si](C)(C)C	2411.2	Semi standard non polar	33892256
Dopamine 3-O-sulfate,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1OS(=O)(=O)O[Si](C)(C)C	2634.8	Standard non polar	33892256
Dopamine 3-O-sulfate,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1OS(=O)(=O)O[Si](C)(C)C	2696.9	Standard polar	33892256
Dopamine 3-O-sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN)C=C1OS(=O)(=O)O	2379.4	Semi standard non polar	33892256
Dopamine 3-O-sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(CCN)=CC=C1O	2325.0	Semi standard non polar	33892256
Dopamine 3-O-sulfate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O)C(OS(=O)(=O)O)=C1	2497.3	Semi standard non polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN)C=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2604.1	Semi standard non polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN)C=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2793.2	Standard non polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN)C=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3120.6	Standard polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O)=C1	2746.9	Semi standard non polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O)=C1	2874.2	Standard non polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O)=C1	3075.4	Standard polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1	2704.1	Semi standard non polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1	2861.7	Standard non polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1	3110.8	Standard polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCC1=CC=C(O)C(OS(=O)(=O)O)=C1)[Si](C)(C)C(C)(C)C	2867.1	Semi standard non polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCC1=CC=C(O)C(OS(=O)(=O)O)=C1)[Si](C)(C)C(C)(C)C	2930.6	Standard non polar	33892256
Dopamine 3-O-sulfate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCC1=CC=C(O)C(OS(=O)(=O)O)=C1)[Si](C)(C)C(C)(C)C	3268.0	Standard polar	33892256
Dopamine 3-O-sulfate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1	2942.0	Semi standard non polar	33892256
Dopamine 3-O-sulfate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1	3208.6	Standard non polar	33892256
Dopamine 3-O-sulfate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1	2976.6	Standard polar	33892256
Dopamine 3-O-sulfate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OS(=O)(=O)O	3128.5	Semi standard non polar	33892256
Dopamine 3-O-sulfate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OS(=O)(=O)O	3272.9	Standard non polar	33892256
Dopamine 3-O-sulfate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OS(=O)(=O)O	3022.2	Standard polar	33892256
Dopamine 3-O-sulfate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	3072.4	Semi standard non polar	33892256
Dopamine 3-O-sulfate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	3311.3	Standard non polar	33892256
Dopamine 3-O-sulfate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	3083.3	Standard polar	33892256
Dopamine 3-O-sulfate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3328.2	Semi standard non polar	33892256
Dopamine 3-O-sulfate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3597.1	Standard non polar	33892256
Dopamine 3-O-sulfate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	2951.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine 3-O-sulfate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9650000000-2db72db7d63697e55bd1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine 3-O-sulfate GC-MS (1 TMS) - 70eV, Positive	splash10-0fl0-9320000000-ace4fcc9cdb2373f726c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine 3-O-sulfate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 10V, Positive-QTOF	splash10-0159-0090000000-b2228f1210694d4037be	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 20V, Positive-QTOF	splash10-014r-1950000000-c9ce0c682709c1c90e1d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 40V, Positive-QTOF	splash10-0gdi-9300000000-f413b35bca5b45692bb0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 10V, Negative-QTOF	splash10-001i-0090000000-c18c16811fdd8fb7e8d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 20V, Negative-QTOF	splash10-0udi-1930000000-37551dd11cac8f51977a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 40V, Negative-QTOF	splash10-0f8i-5900000000-6729c4999d2afb12eec0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 10V, Negative-QTOF	splash10-001i-0090000000-b5c60a607f4b8ffe8309	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 20V, Negative-QTOF	splash10-001j-5090000000-6dc0ebdf64e66d55361a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 40V, Negative-QTOF	splash10-01ow-9100000000-c48fe767b4f0b00bc40e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 10V, Positive-QTOF	splash10-000i-0920000000-5bc862fdad49e730b60a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 20V, Positive-QTOF	splash10-000i-0900000000-751f9057ce9f08d81036	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine 3-O-sulfate 40V, Positive-QTOF	splash10-066u-5900000000-9d59879b17c28b88d464	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0265 +/- 0.011 uM	Adult (>18 years old)	Both	Normal	4055948	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.16 +/- 0.05 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	4055948	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

DOPASF

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Enzyme Details

1. Sulfotransferase 1A3/1A4

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

Showing metabocard for Dopamine 3-O-sulfate (HMDB0006275)

MOL for HMDB0006275 (Dopamine 3-O-sulfate)

3D MOL for HMDB0006275 (Dopamine 3-O-sulfate)

3D SDF for HMDB0006275 (Dopamine 3-O-sulfate)

3D-SDF for HMDB0006275 (Dopamine 3-O-sulfate)

PDB for HMDB0006275 (Dopamine 3-O-sulfate)

3D PDB for HMDB0006275 (Dopamine 3-O-sulfate)

SMILES for HMDB0006275 (Dopamine 3-O-sulfate)

INCHI for HMDB0006275 (Dopamine 3-O-sulfate)

Structure for HMDB0006275 (Dopamine 3-O-sulfate)

3D Structure for HMDB0006275 (Dopamine 3-O-sulfate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes