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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-08 14:59:33 UTC
Update Date2019-07-23 06:03:31 UTC
HMDB IDHMDB0029200
Secondary Accession Numbers
  • HMDB29200
Metabolite Identification
Common NameFerulic acid 4-O-sulfate
DescriptionFerulic acid 4-O-sulfate (CAS: 86321-29-1) is a phenolic acid metabolite. It is also a coffee metabolite found in blood or urine. Ferulic 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?1563861811
Synonyms
ValueSource
Ferulic acid sulfateChEBI
Ferulate sulfateGenerator
Ferulate sulphateGenerator
Ferulic acid sulfuric acidGenerator
Ferulic acid sulphuric acidGenerator
Ferulate 4-sulfateGenerator
Ferulate 4-sulphateGenerator
Ferulic acid 4-sulfuric acidGenerator
Ferulic acid 4-sulphuric acidGenerator
(2E)-3-[3-Methoxy-4-(sulfooxy)phenyl]-2-propenoic acidHMDB
Ferulic acid 4-O-sulfateHMDB
Ferulic acid-4'-sulfateHMDB
(E)-Ferulic acid 4-O-sulfateHMDB
(E)-Ferulic acid-4'-sulfateHMDB
trans-Ferulic acid 4-O-sulfateHMDB
trans-Ferulic acid-4'-sulfateHMDB
Ferulic acid 4-sulfateHMDB
(E)-Ferulic acid 4-O-sulphateHMDB
(E)-Ferulic acid-4'-sulphateHMDB
(E)-Ferulic acid-4’-sulfateHMDB
(E)-Ferulic acid-4’-sulphateHMDB
Ferulic acid 4-O-sulphateHMDB
Ferulic acid 4-sulphateHMDB
Ferulic acid-4'-sulphateHMDB
Ferulic acid-4’-sulfateHMDB
Ferulic acid-4’-sulphateHMDB
trans-Ferulic acid 4-O-sulphateHMDB
trans-Ferulic acid-4'-sulphateHMDB
trans-Ferulic acid-4’-sulfateHMDB
trans-Ferulic acid-4’-sulphateHMDB
Chemical FormulaC10H10O7S
Average Molecular Weight274.247
Monoisotopic Molecular Weight274.014723364
IUPAC Name(2E)-3-[3-methoxy-4-(sulfooxy)phenyl]prop-2-enoic acid
Traditional Name(2E)-3-[3-methoxy-4-(sulfooxy)phenyl]prop-2-enoic acid
CAS Registry Number151481-53-7
SMILES
COC1=C(OS(O)(=O)=O)C=CC(\C=C\C(O)=O)=C1
InChI Identifier
InChI=1S/C10H10O7S/c1-16-9-6-7(3-5-10(11)12)2-4-8(9)17-18(13,14)15/h2-6H,1H3,(H,11,12)(H,13,14,15)/b5-3+
InChI KeyPZPATWACAAOHTJ-HWKANZROSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Phenylsulfate
  • Arylsulfate
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP-0.32ALOGPS
logP1.2ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)-2.2ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity61.5 m³·mol⁻¹ChemAxon
Polarizability24.7 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, Positivesplash10-0a4m-1980000000-0a04a82fe28e63433e61JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gi-6194000000-af9906ac00d0c397e1c1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-cbbeeecc312476cf7b4cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056s-1790000000-c30f07543dbbb35fc47eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-8920000000-1c33c8ea0fa1f33c6eadJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-5f31290999c27432202eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bc-0950000000-498bb5d6540050ba1f92JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-4900000000-3eb0d6bf9f242cb7be06JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029899
KNApSAcK IDNot Available
Chemspider ID4878542
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6305574
PDB IDNot Available
ChEBI ID133508
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Menozzi-Smarrito C, Wong CC, Meinl W, Glatt H, Fumeaux R, Munari C, Robert F, Williamson G, Barron D: First chemical synthesis and in vitro characterization of the potential human metabolites 5-o-feruloylquinic acid 4'-sulfate and 4'-O-glucuronide. J Agric Food Chem. 2011 May 25;59(10):5671-6. doi: 10.1021/jf200272m. Epub 2011 Apr 21. [PubMed:21417257 ]
  2. Amin HP, Czank C, Raheem S, Zhang Q, Botting NP, Cassidy A, Kay CD: Anthocyanins and their physiologically relevant metabolites alter the expression of IL-6 and VCAM-1 in CD40L and oxidized LDL challenged vascular endothelial cells. Mol Nutr Food Res. 2015 Jun;59(6):1095-106. doi: 10.1002/mnfr.201400803. Epub 2015 Apr 30. [PubMed:25787755 ]
  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 ]