Caffeic acid 3-sulfate (CHEM041576)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:34:36 UTC
Update Date2016-11-09 01:22:30 UTC
Accession NumberCHEM041576
Identification
Common NameCaffeic acid 3-sulfate
ClassSmall Molecule
DescriptionAn aryl sulfate that is trans-caffeic acid in which the phenolic hydrogen at position 3 is replaced by a sulfo group. A metabolite from coffee.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Caffeic acid 3'-O-sulfateChEBI
Caffeic acid 3'-sulfateChEBI
Caffeic acid 3-sulphateChEBI
Caffeate 3'-O-sulfateGenerator
Caffeate 3'-O-sulphateGenerator
Caffeic acid 3'-O-sulfuric acidGenerator
Caffeic acid 3'-O-sulphuric acidGenerator
Caffeate 3'-sulfateGenerator
Caffeate 3'-sulphateGenerator
Caffeic acid 3'-sulfuric acidGenerator
Caffeic acid 3'-sulphuric acidGenerator
Caffeate 3-sulfateGenerator
Caffeate 3-sulphateGenerator
Caffeic acid 3-sulfuric acidGenerator
Caffeic acid 3-sulphuric acidGenerator
Caffeate 3-O-sulfateGenerator
Caffeate 3-O-sulphateGenerator
Caffeic acid 3-O-sulfuric acidGenerator
Caffeic acid 3-O-sulphuric acidGenerator
(2E)-3-[4-Hydroxy-3-(sulfooxy)phenyl]-2-propenoic acidHMDB
(e)-Caffeic acid 3-O-sulfateHMDB
(e)-Caffeic acid 3-O-sulphateHMDB
(e)-Caffeic acid 3-sulfateHMDB
(e)-Caffeic acid 3-sulphateHMDB
(e)-Caffeic acid sulfateHMDB
(e)-Caffeic acid sulphateHMDB
3-[4-Hydroxy-3-(sulfooxy)phenyl]-2-propenoic acidHMDB
Caffeic acid 3-O-sulphateHMDB
Caffeic acid 3-sulfateHMDB
Caffeic acid sulfateHMDB
Caffeic acid sulphateHMDB
trans-Caffeic acid 3-O-sulfateHMDB
trans-Caffeic acid 3-O-sulphateHMDB
trans-Caffeic acid 3-sulfateHMDB
trans-Caffeic acid 3-sulphateHMDB
trans-Caffeic acid sulfateHMDB
trans-Caffeic acid sulphateHMDB
Caffeic acid 3-O-sulfateChEBI
Chemical FormulaC9H8O7S
Average Molecular Mass260.221 g/mol
Monoisotopic Mass259.999 g/mol
CAS Registry NumberNot Available
IUPAC Name(2E)-3-[4-hydroxy-3-(sulfooxy)phenyl]prop-2-enoic acid
Traditional Name(2E)-3-[4-hydroxy-3-(sulfooxy)phenyl]prop-2-enoic acid
SMILESOC(=O)\C=C\C1=CC(OS(O)(=O)=O)=C(O)C=C1
InChI IdentifierInChI=1S/C9H8O7S/c10-7-3-1-6(2-4-9(11)12)5-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+
InChI KeyVWQNTRNACRFUCQ-DUXPYHPUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Phenylsulfate
  • Arylsulfate
  • Phenoxy compound
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP-0.37ALOGPS
logP1.7ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.01 m³·mol⁻¹ChemAxon
Polarizability22.35 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xu-1690000000-11cf3ed2d92f173f27ccSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-5019000000-93ef726d3d90fbb1f5d1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-1fbaa79aef2070940a38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0j4l-0790000000-8e3aac299e17766efec2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0q29-7910000000-91f54071865bef100eebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-3dfaf420aef92ccf20c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vi-0950000000-9079a77c64b4f3115a00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03e9-4900000000-942bbc0cc678f5e50dc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-067i-0490000000-7d8c68b79b3ef929f350Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-5290000000-be2fa5928e40e9240e38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05a2-5910000000-15fbdce02e7a7ec55f64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0980000000-d31a92acfa7ffec23a28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0910000000-a11925c7fa34c6c78a65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-825e2ebba2493279eceeSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041706
FooDB IDFDB029871
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30777605
ChEBI ID90242
PubChem Compound ID102261219
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19460943
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20842300
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21481558
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21676405
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23157164
6. 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.
7. 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.
8. Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510