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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-17 03:54:36 UTC
Update Date2019-11-12 17:22:25 UTC
HMDB IDHMDB0131141
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-[4-methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid
Description3-[4-methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid, also known as isoferulic acid 3-O-sulfuric acid or isoferulate 3-O-sulfate, 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. 3-prop-2-enoic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid. 3-[4-methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by Sulfotransferase 1A3 (P0DMM9) and Sulfotransferase enzymes via a -3-O-sulfation-of-phenolic-compound reaction. This -3-O-sulfation-of-phenolic-compound occurs in humans.
Structure
Data?1563875740
Synonyms
ValueSource
3-[4-Methoxy-3-(sulfooxy)phenyl]prop-2-enoateGenerator
3-[4-Methoxy-3-(sulphooxy)phenyl]prop-2-enoateGenerator
3-[4-Methoxy-3-(sulphooxy)phenyl]prop-2-enoic acidGenerator
Isoferulate 3-O-sulfateHMDB
Isoferulate 3-O-sulphateHMDB
Isoferulic acid 3-O-sulfuric acidHMDB
Isoferulic acid 3-O-sulphuric acidHMDB
Chemical FormulaC10H10O7S
Average Molecular Weight274.24
Monoisotopic Molecular Weight274.014723836
IUPAC Name3-[4-methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid
Traditional Name3-[4-methoxy-3-(sulfooxy)phenyl]prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
COC1=C(OS(O)(=O)=O)C=C(C=CC(O)=O)C=C1
InChI Identifier
InChI=1S/C10H10O7S/c1-16-8-4-2-7(3-5-10(11)12)6-9(8)17-18(13,14)15/h2-6H,1H3,(H,11,12)(H,13,14,15)
InChI KeyDCMKMHVTKFJMAU-UHFFFAOYSA-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

Source:

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-0.33ALOGPS
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
Polarizability24.04 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gi-6194000000-ff48317daa64aa6eb3c8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4m-1890000000-c48e01dffb041302e904Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-cbbeeecc312476cf7b4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056s-1790000000-37e98dea95704cf56791Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003s-8920000000-71fc0312e7f46526e17eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-4c23032bf8411c69ae2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bc-0950000000-3a48f734a2bc1f8d5e1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005a-4910000000-409f2f90875227c4ca63Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92000742
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.