Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 03:37:36 UTC
Update Date2022-03-07 02:57:09 UTC
HMDB IDHMDB0041708
Secondary Accession Numbers
  • HMDB41708
Metabolite Identification
Common NameCaffeic acid 4-O-sulfate
DescriptionCaffeic acid 4-O-sulfate, also known as caffeate 4-O-sulfate or caffeic acid 4-sulfuric acid, 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. Based on a literature review very few articles have been published on Caffeic acid 4-O-sulfate.
Structure
Data?1563863693
Synonyms
ValueSource
Caffeate 4-O-sulfateGenerator
Caffeate 4-O-sulphateGenerator
Caffeic acid 4-O-sulfuric acidGenerator
Caffeic acid 4-O-sulphuric acidGenerator
Caffeate 4-sulfateHMDB
Caffeate 4-sulphateHMDB
Caffeic acid 4-sulfuric acidHMDB
Caffeic acid 4-sulphuric acidHMDB
(2E)-3-[3-Hydroxy-4-(sulfooxy)phenyl]prop-2-enoateHMDB
(2E)-3-[3-Hydroxy-4-(sulphooxy)phenyl]prop-2-enoateHMDB
(2E)-3-[3-Hydroxy-4-(sulphooxy)phenyl]prop-2-enoic acidHMDB
(2E)-3-[3-Hydroxy-4-(sulfooxy)phenyl]-2-propenoic acidHMDB
(e)-Caffeic acid 4-O-sulfateHMDB
(e)-Caffeic acid 4-O-sulphateHMDB
(e)-Caffeic acid 4-sulfateHMDB
(e)-Caffeic acid 4-sulphateHMDB
(e)-Caffeic acid sulfateHMDB
(e)-Caffeic acid sulphateHMDB
3-[3-Hydroxy-4-(sulfooxy)phenyl]-2-propenoic acidHMDB
Caffeic acid 4-O-sulphateHMDB
Caffeic acid 4-sulfateHMDB
Caffeic acid 4-sulphateHMDB
Caffeic acid sulfateHMDB
Caffeic acid sulphateHMDB
Caffeic acid-4'-sulfateHMDB
Caffeic acid-4'-sulphateHMDB
Caffeic acid-4’-sulfateHMDB
Caffeic acid-4’-sulphateHMDB
trans-Caffeic acid 4-O-sulfateHMDB
trans-Caffeic acid 4-O-sulphateHMDB
trans-Caffeic acid 4-sulfateHMDB
trans-Caffeic acid 4-sulphateHMDB
trans-Caffeic acid sulfateHMDB
trans-Caffeic acid sulphateHMDB
Caffeic acid 4-O-sulfateHMDB
Chemical FormulaC9H8O7S
Average Molecular Weight260.221
Monoisotopic Molecular Weight259.9990733
IUPAC Name(2E)-3-[3-hydroxy-4-(sulfooxy)phenyl]prop-2-enoic acid
Traditional Name(2E)-3-[3-hydroxy-4-(sulfooxy)phenyl]prop-2-enoic acid
CAS Registry Number151481-51-5
SMILES
OC(=O)\C=C\C1=CC(O)=C(OS(O)(=O)=O)C=C1
InChI Identifier
InChI=1S/C9H8O7S/c10-7-5-6(2-4-9(11)12)1-3-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+
InChI KeySNVAIAITQIIEMQ-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-4-unsubstituted benzenoid
  • 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
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.73 g/LALOGPS
logP-0.36ALOGPS
logP1.7ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)-2.4ChemAxon
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
Polarizability22.62 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+157.73730932474
DeepCCS[M-H]-155.37930932474
DeepCCS[M-2H]-188.3430932474
DeepCCS[M+Na]+163.8330932474
AllCCS[M+H]+154.932859911
AllCCS[M+H-H2O]+151.232859911
AllCCS[M+NH4]+158.332859911
AllCCS[M+Na]+159.332859911
AllCCS[M-H]-149.232859911
AllCCS[M+Na-2H]-149.332859911
AllCCS[M+HCOO]-149.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Caffeic acid 4-O-sulfateOC(=O)\C=C\C1=CC(O)=C(OS(O)(=O)=O)C=C14471.6Standard polar33892256
Caffeic acid 4-O-sulfateOC(=O)\C=C\C1=CC(O)=C(OS(O)(=O)=O)C=C11962.2Standard non polar33892256
Caffeic acid 4-O-sulfateOC(=O)\C=C\C1=CC(O)=C(OS(O)(=O)=O)C=C12367.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Caffeic acid 4-O-sulfate,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=C(OS(=O)(=O)O)C(O)=C12449.7Semi standard non polar33892256
Caffeic acid 4-O-sulfate,1TMS,isomer #2C[Si](C)(C)OC1=CC(/C=C/C(=O)O)=CC=C1OS(=O)(=O)O2460.7Semi standard non polar33892256
Caffeic acid 4-O-sulfate,1TMS,isomer #3C[Si](C)(C)OS(=O)(=O)OC1=CC=C(/C=C/C(=O)O)C=C1O2475.9Semi standard non polar33892256
Caffeic acid 4-O-sulfate,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=C(OS(=O)(=O)O)C(O[Si](C)(C)C)=C12497.1Semi standard non polar33892256
Caffeic acid 4-O-sulfate,2TMS,isomer #2C[Si](C)(C)OC(=O)/C=C/C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O)=C12455.9Semi standard non polar33892256
Caffeic acid 4-O-sulfate,2TMS,isomer #3C[Si](C)(C)OC1=CC(/C=C/C(=O)O)=CC=C1OS(=O)(=O)O[Si](C)(C)C2491.8Semi standard non polar33892256
Caffeic acid 4-O-sulfate,3TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C12495.7Semi standard non polar33892256
Caffeic acid 4-O-sulfate,3TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C12559.2Standard non polar33892256
Caffeic acid 4-O-sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(OS(=O)(=O)O)C(O)=C12726.4Semi standard non polar33892256
Caffeic acid 4-O-sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O)=CC=C1OS(=O)(=O)O2738.9Semi standard non polar33892256
Caffeic acid 4-O-sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(/C=C/C(=O)O)C=C1O2744.6Semi standard non polar33892256
Caffeic acid 4-O-sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(OS(=O)(=O)O)C(O[Si](C)(C)C(C)(C)C)=C13018.6Semi standard non polar33892256
Caffeic acid 4-O-sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(O)=C12983.8Semi standard non polar33892256
Caffeic acid 4-O-sulfate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O)=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C3007.6Semi standard non polar33892256
Caffeic acid 4-O-sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13223.4Semi standard non polar33892256
Caffeic acid 4-O-sulfate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13364.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Caffeic acid 4-O-sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xu-1690000000-2099aa56bc17d6f8dfbc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Caffeic acid 4-O-sulfate GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-5029000000-f3ae7ef7834ca7b22d7d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Caffeic acid 4-O-sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Caffeic acid 4-O-sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 10V, Positive-QTOFsplash10-0006-0090000000-6d7405df313b60db279d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 20V, Positive-QTOFsplash10-03xu-1980000000-2ff5233a16c02db10ab42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 40V, Positive-QTOFsplash10-0690-8910000000-6a92b09121121f341ba82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 10V, Negative-QTOFsplash10-0a4i-0090000000-895e0889ba62c427ad9e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 20V, Negative-QTOFsplash10-01t9-0950000000-c8670832bae0b366e1c72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 40V, Negative-QTOFsplash10-03e9-4900000000-539439543f38aa9043572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 10V, Positive-QTOFsplash10-03dl-0980000000-3dc7f107fbc65c3318a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 20V, Positive-QTOFsplash10-03di-0920000000-89701f174df8154819af2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 40V, Positive-QTOFsplash10-014j-0900000000-55d19e06bcffd3a501792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 10V, Negative-QTOFsplash10-0a4i-0090000000-2459f93a8b832017b2ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 20V, Negative-QTOFsplash10-00kb-7290000000-2342a5604ec0a33d21d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Caffeic acid 4-O-sulfate 40V, Negative-QTOFsplash10-0002-9000000000-b206397b87a65fe63d412021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 940 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 940 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031320
KNApSAcK IDNot Available
Chemspider ID30777608
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21668705
PDB IDNot Available
ChEBI ID176485
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]