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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-10-06 11:20:09 UTC

Update Date

2022-09-22 17:44:13 UTC

HMDB ID

HMDB0155722

Secondary Accession Numbers

None

Metabolite Identification

Common Name

O-Sulfotyrosine

Description

O-Sulfotyrosine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from a reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. O-Sulfotyrosine has been identified as a potential plasma biomarker of reduced kidney function in early chronic kidney disease (CKD), end stage renal disease (ESRD), and hemodialytic clearance (PMID: 31048706 ). Human plasma levels of O-sulfotyrosine were reported to be influenced by genetic variants in the gene ARSA which codes for the enzyme arylsulfatase A (PMID: 24816252 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652308201919302D          

 17 17  0  0  0  0            999 V2000
 9998.2268 9998.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5127 9999.1765    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0995 9999.8905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9240 9999.8905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7946 9998.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.083710000.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7969 9999.9999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.510010000.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2253 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.510010001.2367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7969 9999.1765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.369210000.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.654710000.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.940210000.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9401 9999.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6546 9998.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3692 9999.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
  1 15  1  0  0  0  0
 12  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0155722

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CC=C(OS(O)(=O)=O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO6S/c10-8(9(11)12)5-6-1-3-7(4-2-6)16-17(13,14)15/h1-4,8H,5,10H2,(H,11,12)(H,13,14,15)/t8-/m0/s1

> <INCHI_KEY>
CIQHWLTYGMYQQR-QMMMGPOBSA-N

> <FORMULA>
C9H11NO6S

> <MOLECULAR_WEIGHT>
261.252

> <EXACT_MASS>
261.030707779

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.331021212715246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-[4-(sulfooxy)phenyl]propanoic acid

> <ALOGPS_LOGP>
-1.88

> <JCHEM_LOGP>
-0.735755146588887

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.2967205572310618

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.0905879692341216

> <JCHEM_PKA_STRONGEST_BASIC>
9.450845755294097

> <JCHEM_POLAR_SURFACE_AREA>
126.92

> <JCHEM_REFRACTIVITY>
57.089000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-[4-(sulfooxy)phenyl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-AUG-19         0                                  
HETATM    1  O   UNK     0    8663.3578664.358   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0    8662.0248665.129   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0    8661.2528666.462   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8662.7918666.462   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8660.6838664.358   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8668.6908667.436   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.0218666.666   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.3528667.436   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8672.6878666.666   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8671.3528668.975   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8670.0218665.129   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0    8667.3568666.668   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.0228667.438   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.6888666.668   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.6888665.128   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.0228664.358   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3568665.128   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    7   12                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12   13   17    6                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    1                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0155722
HETATM    1  N1  UNL     1      -2.614  -0.149  -1.279  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.768  -0.341   0.162  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.710   0.505   0.885  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.347   0.094   0.478  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.370  -0.884   1.134  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.650  -1.256   0.735  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.245  -0.642  -0.350  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.514  -1.003  -0.756  1.00  0.00           O  
HETATM    9  S1  UNL     1       4.902  -0.247  -0.155  1.00  0.00           S  
HETATM   10  O2  UNL     1       5.373  -1.032   1.037  1.00  0.00           O  
HETATM   11  O3  UNL     1       5.957  -0.313  -1.233  1.00  0.00           O  
HETATM   12  O4  UNL     1       4.615   1.357   0.233  1.00  0.00           O  
HETATM   13  C7  UNL     1       1.529   0.328  -0.999  1.00  0.00           C  
HETATM   14  C8  UNL     1       0.260   0.704  -0.611  1.00  0.00           C  
HETATM   15  C9  UNL     1      -4.079   0.166   0.618  1.00  0.00           C  
HETATM   16  O5  UNL     1      -4.380   0.084   1.821  1.00  0.00           O  
HETATM   17  O6  UNL     1      -4.941   0.719  -0.300  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.266   0.560  -1.630  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.793  -1.056  -1.746  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.638  -1.416   0.442  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.927   1.553   0.600  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.908   0.374   1.959  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.110  -1.369   1.998  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.173  -2.037   1.291  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.064   1.367   1.044  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.989   0.811  -1.848  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.307   1.466  -1.117  1.00  0.00           H  
HETATM   28  H11 UNL     1      -4.856   1.657  -0.668  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3   15   20
CONECT    3    4   21   22
CONECT    4    5    5   14
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8   13
CONECT    8    9
CONECT    9   10   10   11   11
CONECT    9   12
CONECT   12   25
CONECT   13   14   14   26
CONECT   14   27
CONECT   15   16   16   17
CONECT   17   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-Amino-3-[4-(sulfooxy)phenyl]propanoic acid	ChEBI
(2S)-2-Azanyl-3-(4-sulfooxyphenyl)propanoic acid	ChEBI
L-Tyrosine O-sulfate	ChEBI
O-SulfO-L-tyrosine	ChEBI
Sulfotyrosine	ChEBI
Tyrosine O-sulfate	ChEBI
Tyrosine sulfate	ChEBI
(2S)-2-Amino-3-[4-(sulfooxy)phenyl]propanoate	Generator
(2S)-2-Amino-3-[4-(sulphooxy)phenyl]propanoate	Generator
(2S)-2-Amino-3-[4-(sulphooxy)phenyl]propanoic acid	Generator
(2S)-2-Azanyl-3-(4-sulfooxyphenyl)propanoate	Generator
(2S)-2-Azanyl-3-(4-sulphooxyphenyl)propanoate	Generator
(2S)-2-Azanyl-3-(4-sulphooxyphenyl)propanoic acid	Generator
L-Tyrosine O-sulfuric acid	Generator
L-Tyrosine O-sulphate	Generator
L-Tyrosine O-sulphuric acid	Generator
O-SulphO-L-tyrosine	Generator
Sulphotyrosine	Generator
Tyrosine O-sulfuric acid	Generator
Tyrosine O-sulphate	Generator
Tyrosine O-sulphuric acid	Generator
Tyrosine sulfuric acid	Generator
Tyrosine sulphate	Generator
Tyrosine sulphuric acid	Generator
O(4')-SulphO-L-tyrosine	Generator
O-Decasulfate	MeSH, HMDB
O-Sulfotyrosine	HMDB
O-Sulphotyrosine	Generator

Chemical Formula

C₉H₁₁NO₆S

Average Molecular Weight

261.252

Monoisotopic Molecular Weight

261.030707779

IUPAC Name

(2S)-2-amino-3-[4-(sulfooxy)phenyl]propanoic acid

Traditional Name

(2S)-2-amino-3-[4-(sulfooxy)phenyl]propanoic acid

CAS Registry Number

956-46-7

SMILES

N[C@@H](CC1=CC=C(OS(O)(=O)=O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C9H11NO6S/c10-8(9(11)12)5-6-1-3-7(4-2-6)16-17(13,14)15/h1-4,8H,5,10H2,(H,11,12)(H,13,14,15)/t8-/m0/s1

InChI Key

CIQHWLTYGMYQQR-QMMMGPOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Phenylsulfate
Alpha-amino acid
Amphetamine or derivatives
Arylsulfate
L-alpha-amino acid
Phenoxy compound
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

L-tyrosine derivative (CHEBI:46215 )
O-sulfoamino acid (CHEBI:46215 )

Ontology

Not Available

Placenta (HMDB: HMDB0155722)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31048706)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.9	ALOGPS
logP	-0.74	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	-2.1	ChemAxon
pKa (Strongest Basic)	9.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	126.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.09 m³·mol⁻¹	ChemAxon
Polarizability	23.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	158.748	30932474
DeepCCS	[M-H]-	156.353	30932474
DeepCCS	[M-2H]-	189.458	30932474
DeepCCS	[M+Na]+	164.804	30932474
AllCCS	[M+H]+	156.5	32859911
AllCCS	[M+H-H2O]+	153.0	32859911
AllCCS	[M+NH4]+	159.9	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	151.9	32859911
AllCCS	[M+Na-2H]-	152.2	32859911
AllCCS	[M+HCOO]-	152.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Sulfotyrosine	N[C@@H](CC1=CC=C(OS(O)(=O)=O)C=C1)C(O)=O	3626.3	Standard polar	33892256
O-Sulfotyrosine	N[C@@H](CC1=CC=C(OS(O)(=O)=O)C=C1)C(O)=O	2053.9	Standard non polar	33892256
O-Sulfotyrosine	N[C@@H](CC1=CC=C(OS(O)(=O)=O)C=C1)C(O)=O	2500.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Sulfotyrosine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OS(=O)(=O)O)C=C1	2242.8	Semi standard non polar	33892256
O-Sulfotyrosine,1TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(C[C@H](N)C(=O)O)C=C1	2343.4	Semi standard non polar	33892256
O-Sulfotyrosine,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O	2379.5	Semi standard non polar	33892256
O-Sulfotyrosine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	2254.5	Semi standard non polar	33892256
O-Sulfotyrosine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	2395.6	Standard non polar	33892256
O-Sulfotyrosine,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	3521.4	Standard polar	33892256
O-Sulfotyrosine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O[Si](C)(C)C	2307.1	Semi standard non polar	33892256
O-Sulfotyrosine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O[Si](C)(C)C	2345.6	Standard non polar	33892256
O-Sulfotyrosine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O[Si](C)(C)C	3288.8	Standard polar	33892256
O-Sulfotyrosine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C(=O)O	2408.6	Semi standard non polar	33892256
O-Sulfotyrosine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C(=O)O	2379.6	Standard non polar	33892256
O-Sulfotyrosine,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C(=O)O	3399.4	Standard polar	33892256
O-Sulfotyrosine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O)[Si](C)(C)C	2509.7	Semi standard non polar	33892256
O-Sulfotyrosine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O)[Si](C)(C)C	2438.7	Standard non polar	33892256
O-Sulfotyrosine,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O)[Si](C)(C)C	3480.0	Standard polar	33892256
O-Sulfotyrosine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2323.8	Semi standard non polar	33892256
O-Sulfotyrosine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2478.0	Standard non polar	33892256
O-Sulfotyrosine,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	3060.8	Standard polar	33892256
O-Sulfotyrosine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2457.3	Semi standard non polar	33892256
O-Sulfotyrosine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2505.0	Standard non polar	33892256
O-Sulfotyrosine,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O)C=C1)N([Si](C)(C)C)[Si](C)(C)C	3096.6	Standard polar	33892256
O-Sulfotyrosine,3TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2502.9	Semi standard non polar	33892256
O-Sulfotyrosine,3TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1	2589.0	Standard non polar	33892256
O-Sulfotyrosine,3TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1	3197.8	Standard polar	33892256
O-Sulfotyrosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2470.8	Semi standard non polar	33892256
O-Sulfotyrosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2642.7	Standard non polar	33892256
O-Sulfotyrosine,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2942.0	Standard polar	33892256
O-Sulfotyrosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OS(=O)(=O)O)C=C1	2520.8	Semi standard non polar	33892256
O-Sulfotyrosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(C[C@H](N)C(=O)O)C=C1	2585.6	Semi standard non polar	33892256
O-Sulfotyrosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O	2633.3	Semi standard non polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	2750.6	Semi standard non polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	2921.0	Standard non polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	3509.0	Standard polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2843.6	Semi standard non polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2866.2	Standard non polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3354.4	Standard polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	2905.6	Semi standard non polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	2899.7	Standard non polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3414.9	Standard polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3017.6	Semi standard non polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2922.9	Standard non polar	33892256
O-Sulfotyrosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=C(OS(=O)(=O)O)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3442.6	Standard polar	33892256
O-Sulfotyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3049.8	Semi standard non polar	33892256
O-Sulfotyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3253.5	Standard non polar	33892256
O-Sulfotyrosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3244.8	Standard polar	33892256
O-Sulfotyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3241.4	Semi standard non polar	33892256
O-Sulfotyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3241.3	Standard non polar	33892256
O-Sulfotyrosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3245.6	Standard polar	33892256
O-Sulfotyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3254.0	Semi standard non polar	33892256
O-Sulfotyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3300.3	Standard non polar	33892256
O-Sulfotyrosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3302.0	Standard polar	33892256
O-Sulfotyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3413.7	Semi standard non polar	33892256
O-Sulfotyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3593.3	Standard non polar	33892256
O-Sulfotyrosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3173.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O-Sulfotyrosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Sulfotyrosine 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 - O-Sulfotyrosine 10V, Negative-QTOF	splash10-03dl-0090000000-ab3f61d98b1209cd1831	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Sulfotyrosine 20V, Negative-QTOF	splash10-0006-0490000000-c3ca628707c150500e60	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Sulfotyrosine 40V, Negative-QTOF	splash10-006t-9610000000-9ae5134694e584e8e36a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Sulfotyrosine 10V, Positive-QTOF	splash10-02t9-0090000000-32e215938647538891b3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Sulfotyrosine 20V, Positive-QTOF	splash10-014i-0490000000-4e5a780503504d236da2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Sulfotyrosine 40V, Positive-QTOF	splash10-014i-1910000000-9daeebe25cc8f0327e70	2021-09-24	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

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	31048706	details
Blood	Detected but not Quantified	Not Quantified	Adult (40 years old)	Both	Normal	26317986	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Elderly (>65 years old)	Male	Renal failure with dialysis	26317986	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

448617

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

514186

PDB ID

Not Available

ChEBI ID

46215

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Shin SY, Fauman EB, Petersen AK, Krumsiek J, Santos R, Huang J, Arnold M, Erte I, Forgetta V, Yang TP, Walter K, Menni C, Chen L, Vasquez L, Valdes AM, Hyde CL, Wang V, Ziemek D, Roberts P, Xi L, Grundberg E, Waldenberger M, Richards JB, Mohney RP, Milburn MV, John SL, Trimmer J, Theis FJ, Overington JP, Suhre K, Brosnan MJ, Gieger C, Kastenmuller G, Spector TD, Soranzo N: An atlas of genetic influences on human blood metabolites. Nat Genet. 2014 Jun;46(6):543-550. doi: 10.1038/ng.2982. Epub 2014 May 11. [PubMed:24816252 ]
Velenosi TJ, Thomson BKA, Tonial NC, RaoPeters AAE, Mio MA, Lajoie GA, Garg AX, House AA, Urquhart BL: Untargeted metabolomics reveals N, N, N-trimethyl-L-alanyl-L-proline betaine (TMAP) as a novel biomarker of kidney function. Sci Rep. 2019 May 2;9(1):6831. doi: 10.1038/s41598-019-42992-3. [PubMed:31048706 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for O-Sulfotyrosine (HMDB0155722)

MOL for HMDB0155722 (O-Sulfotyrosine)

3D MOL for HMDB0155722 (O-Sulfotyrosine)

3D SDF for HMDB0155722 (O-Sulfotyrosine)

3D-SDF for HMDB0155722 (O-Sulfotyrosine)

PDB for HMDB0155722 (O-Sulfotyrosine)

3D PDB for HMDB0155722 (O-Sulfotyrosine)

SMILES for HMDB0155722 (O-Sulfotyrosine)

INCHI for HMDB0155722 (O-Sulfotyrosine)

Structure for HMDB0155722 (O-Sulfotyrosine)

3D Structure for HMDB0155722 (O-Sulfotyrosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra