MiMeDB: Showing metabocard for O-Sulfo-L-tyrosine (MMDBc0000837)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 23:04:54 UTC

Update Date

2024-04-30 19:33:47 UTC

Metabolite ID

MMDBc0000837

Metabolite Identification

Common Name

O-Sulfo-L-tyrosine

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>
MMDBc0000837

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₉H₁₁NO₆S

Average Mass

261.252

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.79 g/L	ALOGPS
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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human feces; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	2	Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Bacteroidetes	1	Human feces; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified	Adult (>18 years old)	Not Specified	Normal	HMDB	31048706
Human Blood	Detected but not Quantified	Adult (40 years old)	Both	Normal	HMDB	26317986

External Links

HMDB ID

HMDB0155722

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

References

Synthesis Reference

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-Sulfo-L-tyrosine (MMDBc0000837)

MOL for #<Metabolite:0x00005645c9fc6448>

3D MOL for #<Metabolite:0x00005645c9fc6448>

3D SDF for #<Metabolite:0x00005645c9fc6448>

3D-SDF for #<Metabolite:0x00005645c9fc6448>

PDB for #<Metabolite:0x00005645c9fc6448>

3D PDB for #<Metabolite:0x00005645c9fc6448>

SMILES for #<Metabolite:0x00005645c9fc6448>

INCHI for #<Metabolite:0x00005645c9fc6448>

Structure for #<Metabolite:0x00005645c9fc6448>

3D Structure for #<Metabolite:0x00005645c9fc6448>