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Showing metabocard for Phenol sulphate (HMDB0060015)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-04-09 21:19:47 UTC
Update Date2023-02-21 17:29:40 UTC
HMDB IDHMDB0060015
Secondary Accession Numbers
  • HMDB60015
Metabolite Identification
Common NamePhenol sulphate
DescriptionPhenol sulphate, also known as phenylsulfate or aryl sulphate, belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfate group conjugated to a phenyl group. In normal humans, phenol sulphate is primarily a gut-derived metabolite that arises from the activity of the bacterial enzyme tyrosine phenol-lyase, which is responsible for the synthesis of phenol from dietary tyrosine (PMID: 31015435 ). Phenol sulphate can also arise from the consumption of phenol or from phenol poisoning (PMID: 473790 ). Phenol sulphate is produced from the conjugation of phenol with sulphate in the liver. In particular, phenol sulphate can be biosynthesized from phenol and phosphoadenosine phosphosulfate through the action of the enzyme sulfotransferase 1A1 in the liver. Phenol sulphate can be found in most mammals (mice, rats, sheep, dogs, humans) and likely most animals. Phenol sulphate is a uremic toxin (PMID: 30068866 ). It is a protein-bound uremic solute that induces reactive oxygen species (ROS) production and decreases glutathione levels, rendering cells vulnerable to oxidative stress (PMID: 29474405 ). In experimental models of diabetes, phenol sulphate administration has been shown to induce albuminuria and podocyte damage. In a diabetic patient cohort, phenol sulphate levels were found to significantly correlate with basal and predicted 2-year progression of albuminuria in patients with microalbuminuria (PMID: 31015435 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060015 (Phenol sulphate)

  Mrv1652304062013152D          

 11 11  0  0  0  0            999 V2000
    4.1237   -5.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8382   -6.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8382   -6.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237   -7.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092   -6.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092   -6.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237   -4.8476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092   -4.4351    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948   -4.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8217   -3.7206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967   -5.1496    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
M  END
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3D MOL for HMDB0060015 (Phenol sulphate)

HMDB0060015
     RDKit          3D
Phenol sulphate
 17 17  0  0  0  0  0  0  0  0999 V2000
    1.9393   -0.0342   -1.8397 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663   -0.0715   -0.4880 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.4558   -1.2903   -0.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870    1.2715   -0.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237   -0.1110    0.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601   -0.0993    0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321    1.0841    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9914    1.0675    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455   -0.1383   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9540   -1.3326    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949   -1.3088    0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6233    1.5889    0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0865    2.0269    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117    2.0270    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7021   -0.1479   -0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734   -2.2832   -0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640   -2.2487    0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  4 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
 11 17  1  0
M  END
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3D SDF for HMDB0060015 (Phenol sulphate)

  Mrv1652304062013152D          

 11 11  0  0  0  0            999 V2000
    4.1237   -5.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8382   -6.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8382   -6.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237   -7.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092   -6.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092   -6.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237   -4.8476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092   -4.4351    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948   -4.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8217   -3.7206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967   -5.1496    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060015

> <DATABASE_NAME>
hmdb

> <SMILES>
OS(=O)(=O)OC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O4S/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H,(H,7,8,9)

> <INCHI_KEY>
CTYRPMDGLDAWRQ-UHFFFAOYSA-N

> <FORMULA>
C6H6O4S

> <MOLECULAR_WEIGHT>
174.174

> <EXACT_MASS>
173.99867937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
15.0326808114296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
phenyloxidanesulfonic acid

> <ALOGPS_LOGP>
-0.75

> <JCHEM_LOGP>
1.194367148

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.225815209389176

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
38.0307

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylsulfate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0060015 (Phenol sulphate)

HMDB0060015
     RDKit          3D
Phenol sulphate
 17 17  0  0  0  0  0  0  0  0999 V2000
    1.9393   -0.0342   -1.8397 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663   -0.0715   -0.4880 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.4558   -1.2903   -0.3270 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870    1.2715   -0.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237   -0.1110    0.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0601   -0.0993    0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321    1.0841    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9914    1.0675    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455   -0.1383   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9540   -1.3326    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949   -1.3088    0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6233    1.5889    0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0865    2.0269    0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117    2.0270    0.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7021   -0.1479   -0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734   -2.2832   -0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640   -2.2487    0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  4 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
 11 17  1  0
M  END
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PDB for HMDB0060015 (Phenol sulphate)

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0       7.698 -10.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.031 -11.359   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.031 -12.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.698 -13.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.364 -12.899   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.364 -11.359   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.698  -9.049   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       6.364  -8.279   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0       5.030  -7.509   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       7.134  -6.945   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.594  -9.613   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0060015 (Phenol sulphate)

COMPND    HMDB0060015
HETATM    1  O1  UNL     1       1.939  -0.034  -1.840  1.00  0.00           O  
HETATM    2  S1  UNL     1       2.566  -0.072  -0.488  1.00  0.00           S  
HETATM    3  O2  UNL     1       3.456  -1.290  -0.327  1.00  0.00           O  
HETATM    4  O3  UNL     1       3.587   1.272  -0.369  1.00  0.00           O  
HETATM    5  O4  UNL     1       1.424  -0.111   0.736  1.00  0.00           O  
HETATM    6  C1  UNL     1       0.060  -0.099   0.488  1.00  0.00           C  
HETATM    7  C2  UNL     1      -0.632   1.084   0.401  1.00  0.00           C  
HETATM    8  C3  UNL     1      -1.991   1.068   0.153  1.00  0.00           C  
HETATM    9  C4  UNL     1      -2.645  -0.138  -0.008  1.00  0.00           C  
HETATM   10  C5  UNL     1      -1.954  -1.333   0.078  1.00  0.00           C  
HETATM   11  C6  UNL     1      -0.595  -1.309   0.327  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.623   1.589   0.562  1.00  0.00           H  
HETATM   13  H2  UNL     1      -0.086   2.027   0.533  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.512   2.027   0.090  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.702  -0.148  -0.201  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.473  -2.283  -0.049  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.064  -2.249   0.392  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    4   12
CONECT    5    6
CONECT    6    7    7   11
CONECT    7    8   13
CONECT    8    9    9   14
CONECT    9   10   15
CONECT   10   11   11   16
CONECT   11   17
END
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SMILES for HMDB0060015 (Phenol sulphate)

OS(=O)(=O)OC1=CC=CC=C1
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INCHI for HMDB0060015 (Phenol sulphate)

InChI=1S/C6H6O4S/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H,(H,7,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Phenol sulfateChEBI
PhenylsulfateChEBI
Phenol sulfuric acidGenerator
Phenol sulphuric acidGenerator
Phenylsulfuric acidGenerator
PhenylsulphateGenerator
Phenylsulphuric acidGenerator
Aryl sulfuric acidHMDB
Aryl sulphateHMDB
Aryl sulphuric acidHMDB
Phenylsulfate, sodium saltHMDB
Phenylsulfate, potassium saltHMDB
Phenyl hydrogen sulfateHMDB
Phenyl sulfateHMDB
Phenol sulphateGenerator
Chemical FormulaC6H6O4S
Average Molecular Weight174.174
Monoisotopic Molecular Weight173.99867937
IUPAC Namephenyloxidanesulfonic acid
Traditional Namephenylsulfate
CAS Registry Number937-34-8
SMILES
OS(=O)(=O)OC1=CC=CC=C1
InChI Identifier
InChI=1S/C6H6O4S/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H,(H,7,8,9)
InChI KeyCTYRPMDGLDAWRQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassArylsulfates
Direct ParentPhenylsulfates
Alternative Parents
Substituents
  • Phenylsulfate
  • Phenoxy compound
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDBSALT002236
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02180
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74426
PDB IDNot Available
ChEBI ID27905
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. Sulfotransferase 1A1
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 catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
Gene Name:
SULT1A1
Uniprot ID:
P50225
Molecular weight:
34165.13
Reactions
Phosphoadenosine phosphosulfate + Phenol → Adenosine 3',5'-diphosphate + Phenol sulphatedetails
Enzyme Details
2. Sulfotransferase 1A2
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 catecholamines, phenolic drugs and neurotransmitters. Is also responsible for the sulfonation and activation of minoxidil. Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
Gene Name:
SULT1A2
Uniprot ID:
P50226
Molecular weight:
34310.43
Reactions
Phosphoadenosine phosphosulfate + Phenol → Adenosine 3',5'-diphosphate + Phenol sulphatedetails
Enzyme Details
3. 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
Reactions
Phosphoadenosine phosphosulfate + Phenol → Adenosine 3',5'-diphosphate + Phenol sulphatedetails