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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-09-12 18:57:27 UTC
Update Date2020-11-09 23:30:14 UTC
HMDB IDHMDB0124993
Secondary Accession NumbersNone
Metabolite Identification
Common NameProtocatechuic acid 3-O-sulfate
DescriptionProtocatechuic acid sulfate, also known as 3,4-DHBA sulfate, is an endogenous phenolic acid metabolite found to be elevated in mice urine after rye-bran supplemented diets which makes this compound a potential urinary biomarker of whole grain intake (PMID: 25944556 ). BioTransformer predicts that protocatechuic acid 3-O-sulfate is a product of 3,4-dihydroxybenzoic acid metabolism via a 3-O-sulfation-of-phenolic-compound reaction catalyzed by sulfotransferase 1A3 (P0DMM9) and sulfotransferase enzymes (PMID: 30612223 ).
Structure
Data?1563874918
Synonyms
ValueSource
3,4-Dihydroxybenzoate 3-O-sulfateGenerator
3,4-Dihydroxybenzoate 3-O-sulphateGenerator
3,4-Dihydroxybenzoic acid 3-O-sulfuric acidGenerator
3,4-Dihydroxybenzoic acid 3-O-sulphuric acidGenerator
4-Hydroxy-3-(sulfooxy)benzoateGenerator
4-Hydroxy-3-(sulphooxy)benzoateGenerator
4-Hydroxy-3-(sulphooxy)benzoic acidGenerator
4-Hydroxy-3-(sulfooxy)benzoic acidHMDB
5-Carboxy-2-hydroxyphenyl sulfateHMDB
5-Carboxy-2-hydroxyphenyl sulphateHMDB
Protocatechuic acid 3-sulfateHMDB
Protocatechuic acid 3-sulphateHMDB
Protocatechuic acid sulfateHMDB
Protocatechuic acid sulphateHMDB
3,4-DHBA sulfateHMDB
3,4-DHBA sulphateHMDB
Chemical FormulaC7H6O7S
Average Molecular Weight234.18
Monoisotopic Molecular Weight233.983423707
IUPAC Name4-hydroxy-3-(sulfooxy)benzoic acid
Traditional Name4-hydroxy-3-(sulfooxy)benzoic acid
CAS Registry Number76496-11-2
SMILES
OC(=O)C1=CC(OS(O)(=O)=O)=C(O)C=C1
InChI Identifier
InChI=1S/C7H6O7S/c8-5-2-1-4(7(9)10)3-6(5)14-15(11,12)13/h1-3,8H,(H,9,10)(H,11,12,13)
InChI KeyGSFKEOSQCKWCLH-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
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Phenoxy compound
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP-0.71ALOGPS
logP1.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)-2.7ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.27 m³·mol⁻¹ChemAxon
Polarizability19.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.62231661259
DarkChem[M-H]-147.82931661259
DeepCCS[M+H]+153.16930932474
DeepCCS[M-H]-150.77330932474
DeepCCS[M-2H]-184.19130932474
DeepCCS[M+Na]+159.08130932474
AllCCS[M+H]+149.032859911
AllCCS[M+H-H2O]+145.132859911
AllCCS[M+NH4]+152.632859911
AllCCS[M+Na]+153.632859911
AllCCS[M-H]-139.832859911
AllCCS[M+Na-2H]-140.232859911
AllCCS[M+HCOO]-140.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Protocatechuic acid 3-O-sulfateOC(=O)C1=CC(OS(O)(=O)=O)=C(O)C=C13893.6Standard polar33892256
Protocatechuic acid 3-O-sulfateOC(=O)C1=CC(OS(O)(=O)=O)=C(O)C=C11696.6Standard non polar33892256
Protocatechuic acid 3-O-sulfateOC(=O)C1=CC(OS(O)(=O)=O)=C(O)C=C12020.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Protocatechuic acid 3-O-sulfate,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O)C(OS(=O)(=O)O)=C12095.6Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(C(=O)O)C=C1OS(=O)(=O)O2129.8Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,1TMS,isomer #3C[Si](C)(C)OS(=O)(=O)OC1=CC(C(=O)O)=CC=C1O2173.3Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O)=C12103.9Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C)=C12112.8Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(C(=O)O)C=C1OS(=O)(=O)O[Si](C)(C)C2146.9Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)=C12159.1Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)=C12323.7Standard non polar33892256
Protocatechuic acid 3-O-sulfate,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C)=C12667.2Standard polar33892256
Protocatechuic acid 3-O-sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O)C(OS(=O)(=O)O)=C12385.3Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)O)C=C1OS(=O)(=O)O2420.4Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(C(=O)O)=CC=C1O2440.0Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O)=C12630.0Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C12632.8Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)O)C=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C2660.9Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C12842.7Semi standard non polar33892256
Protocatechuic acid 3-O-sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C13106.0Standard non polar33892256
Protocatechuic acid 3-O-sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C12906.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Protocatechuic acid 3-O-sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uyi-1930000000-dbe378b15d10b18bfc8d2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protocatechuic acid 3-O-sulfate GC-MS (2 TMS) - 70eV, Positivesplash10-059i-7094000000-250fc934a1cd3def170a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protocatechuic acid 3-O-sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Protocatechuic acid 3-O-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 - Protocatechuic acid 3-O-sulfate 10V, Positive-QTOFsplash10-001i-0090000000-ce78d31adc86e11036a92017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 20V, Positive-QTOFsplash10-05o0-1980000000-65650bc6469bbeb3ff822017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 40V, Positive-QTOFsplash10-0udi-9410000000-f022bd1eab2dd55681362017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 10V, Negative-QTOFsplash10-001i-0490000000-a6fe4c80266f8e0d57902017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 20V, Negative-QTOFsplash10-0pbi-0910000000-95dfcda1a97998c39e922017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 40V, Negative-QTOFsplash10-0a4i-2900000000-d2e3d6937cfcba24199a2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 10V, Negative-QTOFsplash10-001i-0090000000-87648273c9aefe644cb12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 20V, Negative-QTOFsplash10-0019-0960000000-40ee51c333f6079d686d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 40V, Negative-QTOFsplash10-014j-9100000000-88a140d83590944a85822021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 10V, Positive-QTOFsplash10-015i-0490000000-bed33871b3ace11b6bc42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 20V, Positive-QTOFsplash10-05nr-0930000000-348a1c3eb47e39ef970e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Protocatechuic acid 3-O-sulfate 40V, Positive-QTOFsplash10-0zg0-9600000000-33101aed9a8c8c7be6e32021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031322
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71316222
PDB IDNot Available
ChEBI IDNot Available
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. Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]
  2. Pekkinen J, Rosa-Sibakov N, Micard V, Keski-Rahkonen P, Lehtonen M, Poutanen K, Mykkanen H, Hanhineva K: Amino acid-derived betaines dominate as urinary markers for rye bran intake in mice fed high-fat diet--A nontargeted metabolomics study. Mol Nutr Food Res. 2015 Aug;59(8):1550-62. doi: 10.1002/mnfr.201500066. Epub 2015 May 28. [PubMed:25944556 ]
  3. 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 ]