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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-01-09 12:11:23 UTC
Update Date2020-11-09 23:21:27 UTC
HMDB IDHMDB0059724
Secondary Accession Numbers
  • HMDB0061713
  • HMDB59724
  • HMDB61713
Metabolite Identification
Common NamePyrocatechol sulfate
DescriptionPyrocatechol sulfate, also known as 1,2-benzenediol mono(hydrogen sulfate) and 2-aminophenol sulfate, is classified as a member of the class of compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. Pyrocatechol sulfate is considered to be slightly soluble (in water) and an extremely strong acidic compound. Pyrocatechol sulfate is a benzoxazinoid metabolite. It is a potential urinary biomarker of whole grain intake (PMID: 27805021 ).
Structure
Data?1563865966
Synonyms
ValueSource
(2-Hydroxyphenyl)oxidanesulfonic acidChEBI
1,2-Benzenediol mono(hydrogen sulfate)ChEBI
1,2-Benzenediol mono(hydrogen sulphate)ChEBI
Catechol monosulfateChEBI
Catechol sulfateChEBI
Pyrocatechol hydrogen sulfateChEBI
Pyrocatechol monosulfateChEBI
(2-Hydroxyphenyl)oxidanesulfonateGenerator
(2-Hydroxyphenyl)oxidanesulphonateGenerator
(2-Hydroxyphenyl)oxidanesulphonic acidGenerator
1,2-Benzenediol mono(hydrogen sulfuric acid)Generator
1,2-Benzenediol mono(hydrogen sulphuric acid)Generator
Catechol monosulfuric acidGenerator
Catechol monosulphateGenerator
Catechol monosulphuric acidGenerator
Catechol sulfuric acidGenerator
Catechol sulphateGenerator
Catechol sulphuric acidGenerator
Pyrocatechol hydrogen sulfuric acidGenerator
Pyrocatechol hydrogen sulphateGenerator
Pyrocatechol hydrogen sulphuric acidGenerator
Pyrocatechol monosulfuric acidGenerator
Pyrocatechol monosulphateGenerator
Pyrocatechol monosulphuric acidGenerator
Pyrocatechol sulfuric acidGenerator
Pyrocatechol sulphateGenerator
Pyrocatechol sulphuric acidGenerator
Catechol 1-O-sulfateHMDB
Catechol 1-O-sulfuric acidHMDB
Catechol 1-O-sulphuric acidHMDB
2-Aminophenol sulfateHMDB
Pyrocatechol sulfateHMDB
Chemical FormulaC6H6O5S
Average Molecular Weight190.174
Monoisotopic Molecular Weight189.993593992
IUPAC Name(2-hydroxyphenyl)oxidanesulfonic acid
Traditional Name(2-hydroxyphenyl)oxidanesulfonic acid
CAS Registry Number4918-96-1
SMILES
OC1=C(OS(O)(=O)=O)C=CC=C1
InChI Identifier
InChI=1S/C6H6O5S/c7-5-3-1-2-4-6(5)11-12(8,9)10/h1-4,7H,(H,8,9,10)
InChI KeyMZPWKJZDOCIALD-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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 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
Disposition

Biological location

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
PropertyValueSource
Water Solubility6.23 g/LALOGPS
logP-0.81ALOGPS
logP1.54ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)-2.4ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.01 m³·mol⁻¹ChemAxon
Polarizability15.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+136.64930932474
DeepCCS[M-H]-134.09230932474
DeepCCS[M-2H]-169.91930932474
DeepCCS[M+Na]+145.17930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pyrocatechol sulfateOC1=C(OS(O)(=O)=O)C=CC=C13122.8Standard polar33892256
Pyrocatechol sulfateOC1=C(OS(O)(=O)=O)C=CC=C11496.2Standard non polar33892256
Pyrocatechol sulfateOC1=C(OS(O)(=O)=O)C=CC=C11575.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyrocatechol sulfate,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC=C1OS(=O)(=O)O1720.9Semi standard non polar33892256
Pyrocatechol sulfate,1TMS,isomer #2C[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1O1616.4Semi standard non polar33892256
Pyrocatechol sulfate,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C1726.9Semi standard non polar33892256
Pyrocatechol sulfate,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C1813.6Standard non polar33892256
Pyrocatechol sulfate,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C2249.9Standard polar33892256
Pyrocatechol sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC=C1OS(=O)(=O)O1964.1Semi standard non polar33892256
Pyrocatechol sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=CC=C1O1866.9Semi standard non polar33892256
Pyrocatechol sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C2191.7Semi standard non polar33892256
Pyrocatechol sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C2329.3Standard non polar33892256
Pyrocatechol sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C2423.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pyrocatechol sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bti-3900000000-e6f53d18ac22c7f5bfe92017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrocatechol sulfate GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-6910000000-80237dcbd0d19fe9a3922017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrocatechol sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 10V, Positive-QTOFsplash10-0006-0900000000-e1185fdf71a2405723c52017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 20V, Positive-QTOFsplash10-03dl-1900000000-f40e0d29b8b6a74dd3f42017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 40V, Positive-QTOFsplash10-0udi-9100000000-dc63c933049bc6dd67752017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 10V, Negative-QTOFsplash10-000i-0900000000-1f7ed2ebb353e20269a02017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 20V, Negative-QTOFsplash10-0a4i-1900000000-d6dda28db9ba8ee670d62017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 40V, Negative-QTOFsplash10-0a4i-9800000000-36d37bd38c5d133fdcbc2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 10V, Negative-QTOFsplash10-000i-0900000000-65e842416b97970070f92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 20V, Negative-QTOFsplash10-000i-1900000000-a74fdd722d14d05c3f522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 40V, Negative-QTOFsplash10-0002-9300000000-2f6a02e142d2ef82baaa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 10V, Positive-QTOFsplash10-01ox-0900000000-1590fbbb0009f5db59812021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 20V, Positive-QTOFsplash10-01q9-9800000000-a3950de0d98e729d8c8f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrocatechol sulfate 40V, Positive-QTOFsplash10-0w29-9000000000-a4a9c033315ddd0f0d2d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031315
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3083879
PDB IDNot Available
ChEBI ID68505
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
  1. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
  2. Zhu Y, Wang P, Sha W, Sang S: Urinary Biomarkers of Whole Grain Wheat Intake Identified by Non-targeted and Targeted Metabolomics Approaches. Sci Rep. 2016 Nov 2;6:36278. doi: 10.1038/srep36278. [PubMed:27805021 ]
  3. 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 ]
  4. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]