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Showing Compound Caffeic acid 3-glucoside (FDB007443)

Record Information
Version1.0
Creation date2010-04-08 22:07:37 UTC
Update date2019-11-26 03:01:39 UTC
Primary IDFDB007443
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCaffeic acid 3-glucoside
DescriptionCaffeic acid 3-glucoside is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Caffeic acid 3-glucoside is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Caffeic acid 3-glucoside can be found in american cranberry, which makes caffeic acid 3-glucoside a potential biomarker for the consumption of this food product.
CAS Number24959-81-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility6.24 g/LALOGPS
logP-0.61ALOGPS
logP-0.74ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.17 m³·mol⁻¹ChemAxon
Polarizability32.44 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H18O9
IUPAC name(2E)-3-(4-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-5-7(1-3-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+/t10-,12-,13+,14-,15-/m1/s1
InChI KeyQOPSZFXPZWQLOG-VHCZEJTMSA-N
Isomeric SMILES[H]\C(=C(\[H])C1=CC(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)=C(O)C=C1)C(O)=O
Average Molecular Weight342.3
Monoisotopic Molecular Weight342.09508216
Classification
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hexose monosaccharide
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • O-glycosyl compound
  • Styrene
  • Phenol ether
  • Phenoxy compound
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01sl-0916000000-e677e480f325aeeaf5312016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0900000000-1e83f1ba36a7ce61b3ae2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900000000-748ad099a27ea54d22ba2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-2928000000-88b5911db1f82a296ebe2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1911000000-5f8771b2b4e5a3712d4d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01u3-2900000000-614d23c371e61247c8012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901000000-514f52cf631674533b292021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0901000000-90fe068e015786922d512021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-1910000000-9027d46fe5f0b7b47d342021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0409000000-a46e9c18202ca539f6262021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0041-0950000000-eb9b37358e2d2872dc9b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-0900000000-afb4cbb449fbf6430a6c2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCAFFEIC-ACID-3-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).