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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-12 03:42:55 UTC
Update Date2019-07-23 06:35:03 UTC
HMDB IDHMDB0041788
Secondary Accession Numbers
  • HMDB41788
Metabolite Identification
Common NameVanillic acid 4-O-sulfate
DescriptionVanillic acid 4-O-sulfate is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ). Vanillic acid 4-O-sulfate was found to be elevated in rat urine after whole rye consumption which makes this compound a potential urinary biomarker of whole grain intake (PMID: 26862900 ).
Structure
Data?1563863703
Synonyms
ValueSource
Vanillate 4-sulfateGenerator
Vanillate 4-sulphateGenerator
Vanillic acid 4-sulfuric acidGenerator
Vanillic acid 4-sulphuric acidGenerator
3-Methoxy-4-(sulfooxy)benzoateGenerator
3-Methoxy-4-(sulphooxy)benzoateGenerator
3-Methoxy-4-(sulphooxy)benzoic acidGenerator
3-Methoxy-4-(sulfooxy)benzoic acidHMDB
Vanillic acid 4-sulfateHMDB
Vanillic acid 4-sulphateHMDB
Vanillic acid sulfateHMDB
Vanillic acid sulphateHMDB
Vanillic acid-4-O-sulfateHMDB
Vanillic acid-4-O-sulphateHMDB
Chemical FormulaC8H8O7S
Average Molecular Weight248.21
Monoisotopic Molecular Weight247.9990733
IUPAC Name3-methoxy-4-(sulfooxy)benzoic acid
Traditional Name3-methoxy-4-(sulfooxy)benzoic acid
CAS Registry Number71235-86-4
SMILES
COC1=C(OS(O)(=O)=O)C=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C8H8O7S/c1-14-7-4-5(8(9)10)2-3-6(7)15-16(11,12)13/h2-4H,1H3,(H,9,10)(H,11,12,13)
InChI KeyTXRKUXPAEPOCIX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • Phenylsulfate
  • M-methoxybenzoic acid or derivatives
  • Arylsulfate
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

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
Water Solubility2.38 g/LALOGPS
logP-0.77ALOGPS
logP0.69ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)-2.6ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.75 m³·mol⁻¹ChemAxon
Polarizability21.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-1960000000-0504414d58a59a1325f6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9272000000-d57b9fca4e862e904773JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-1c987472df7b6ef1cd78JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1960000000-b60b95a52bda88dfb605JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-9620000000-0842cb37f9c7777e6d12JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-2b59120eb186bb6911a9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxs-0940000000-0d684f8d4fbf918cac00JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1900000000-8a0487cf7234e41fff61JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029964
KNApSAcK IDNot Available
Chemspider ID339308
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound382946
PDB IDNot Available
ChEBI ID88847
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [PubMed:22827565 ]
  2. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]
  3. Ounnas F, Prive F, Salen P, Gaci N, Tottey W, Calani L, Bresciani L, Lopez-Gutierrez N, Hazane-Puch F, Laporte F, Brugere JF, Del Rio D, Demeilliers C, de Lorgeril M: Whole Rye Consumption Improves Blood and Liver n-3 Fatty Acid Profile and Gut Microbiota Composition in Rats. PLoS One. 2016 Feb 10;11(2):e0148118. doi: 10.1371/journal.pone.0148118. eCollection 2016. [PubMed:26862900 ]
  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 ]