Showing metabocard for Phenol sulphate (BMDB0096202)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2020-03-10 17:02:52 UTC
Update Date2021-01-12 22:02:02 UTC
BMDB IDBMDB0096202
Secondary Accession Numbers
  • BMDB96202
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. Phenol sulphate can 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, bovine, 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
Thumb
MOLSDFPDBSMILESInChI
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 NumberNot Available
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.75ALOGPS
logP1.19ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)-2.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.03 m³·mol⁻¹ChemAxon
Polarizability15.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9400000000-79584f1aca1b56554519View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-c57b61490132dfa2f1b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-3900000000-d93d2fe0c147af808fdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-d5618f41e4a61b177231View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-9500000000-f08a7354692c9a6009dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9200000000-a0788af7f51ce46e786eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-f8148fa88a5c80a5a60cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-1121fe37163f4f436167View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-002b0226f6cf4491fd4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-d492330baf8658d93b98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-585c639dc8140c1fbf20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-7bd83f0bf390952fb503View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-ff32c1b87d0a3d4d9ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-ff32c1b87d0a3d4d9ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-3cd30e729ac6dc325c35View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0060015
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kikuchi K, Saigusa D, Kanemitsu Y, Matsumoto Y, Thanai P, Suzuki N, Mise K, Yamaguchi H, Nakamura T, Asaji K, Mukawa C, Tsukamoto H, Sato T, Oikawa Y, Iwasaki T, Oe Y, Tsukimi T, Fukuda NN, Ho HJ, Nanto-Hara F, Ogura J, Saito R, Nagao S, Ohsaki Y, Shimada S, Suzuki T, Toyohara T, Mishima E, Shima H, Akiyama Y, Akiyama Y, Ichijo M, Matsuhashi T, Matsuo A, Ogata Y, Yang CC, Suzuki C, Breeggemann MC, Heymann J, Shimizu M, Ogawa S, Takahashi N, Suzuki T, Owada Y, Kure S, Mano N, Soga T, Wada T, Kopp JB, Fukuda S, Hozawa A, Yamamoto M, Ito S, Wada J, Tomioka Y, Abe T: Gut microbiome-derived phenyl sulfate contributes to albuminuria in diabetic kidney disease. Nat Commun. 2019 Apr 23;10(1):1835. doi: 10.1038/s41467-019-09735-4. [PubMed:31015435 ]
  2. Kao J, Bridges JW, Faulkner JK: Metabolism of [14C]phenol by sheep, pig and rat. Xenobiotica. 1979 Mar;9(3):141-7. doi: 10.3109/00498257909038714. [PubMed:473790 ]
  3. Kanemitsu Y, Tsukamoto H, Matsumoto Y, Nozawa-Kumada K, Kondo Y, Abe T, Tomioka Y: Generation and Characterization of Anti-phenyl Sulfate Monoclonal Antibodies and a Potential Use for Phenyl Sulfate Analysis in Human Blood. Biol Pharm Bull. 2018;41(8):1170-1177. doi: 10.1248/bpb.b17-00925. [PubMed:30068866 ]
  4. Edamatsu T, Fujieda A, Itoh Y: Phenyl sulfate, indoxyl sulfate and p-cresyl sulfate decrease glutathione level to render cells vulnerable to oxidative stress in renal tubular cells. PLoS One. 2018 Feb 23;13(2):e0193342. doi: 10.1371/journal.pone.0193342. eCollection 2018. [PubMed:29474405 ]

Enzymes

Enzyme Details
1. Sulfotransferase 1A1
General function:
Involved in aryl 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 (By similarity).
Gene Name:
SULT1A1
Uniprot ID:
P50227
Molecular weight:
34184.0
Reactions
Phosphoadenosine phosphosulfate + Phenol → Adenosine 3',5'-diphosphate + Phenol sulphatedetails