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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-12 03:37:29 UTC
Update Date2019-06-18 17:01:50 UTC
HMDB IDHMDB0041706
Secondary Accession Numbers
  • HMDB41706
Metabolite Identification
Common NameCaffeic acid 3-O-sulfate
DescriptionCaffeic acid 3-O-sulfate (CAS: 1208232-16-9) is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ). Caffeic acid 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?1560546852
Synonyms
ValueSource
Caffeic acid 3'-O-sulfateChEBI
Caffeic acid 3'-sulfateChEBI
Caffeic acid 3-O-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-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
(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
Chemical FormulaC9H8O7S
Average Molecular Weight260.221
Monoisotopic Molecular Weight259.9990733
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
CAS Registry Number151481-52-6
SMILES
OC(=O)\C=C\C1=CC(OS(O)(=O)=O)=C(O)C=C1
InChI Identifier
InChI=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
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 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xu-1690000000-11cf3ed2d92f173f27ccJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-5019000000-93ef726d3d90fbb1f5d1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-1fbaa79aef2070940a38JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0j4l-0790000000-8e3aac299e17766efec2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0q29-7910000000-91f54071865bef100eebJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-3dfaf420aef92ccf20c3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vi-0950000000-9079a77c64b4f3115a00JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03e9-4900000000-942bbc0cc678f5e50dc1JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 941 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029871
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102261219
PDB IDNot Available
ChEBI ID90242
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  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 ]