Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2018-01-25 19:27:14 UTC
Primary IDFDB000223
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEllagic acid arabinoside
DescriptionEllagic acid arabinoside is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Ellagic acid arabinoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Ellagic acid arabinoside can be found in red raspberry, which makes ellagic acid arabinoside a potential biomarker for the consumption of this food product.
CAS Number302-72-7
Structure
Thumb
Synonyms
SynonymSource
4-Arabinosyl-ellagic aciddb_source
Ellagic acid 4-a-L-arabinofuranosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility3.4 g/LALOGPS
logP0.77ALOGPS
logP0.68ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)5.83ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area192.44 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.79 m³·mol⁻¹ChemAxon
Polarizability39.16 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC19H14O12
IUPAC name7,13,14-trihydroxy-6-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione
InChI IdentifierInChI=1S/C19H14O12/c20-6-1-4-9-10-5(18(27)30-15(9)12(6)23)2-8(13(24)16(10)31-17(4)26)29-19-14(25)11(22)7(21)3-28-19/h1-2,7,11,14,19-25H,3H2/t7-,11-,14+,19-/m0/s1
InChI KeyKNURQRIPZJJYQO-FYZLSVPNSA-N
Isomeric SMILES[H][C@]1(O)CO[C@@]([H])(OC2=CC3=C4C(OC(=O)C5=CC(O)=C(O)C(OC3=O)=C45)=C2O)[C@]([H])(O)[C@@]1([H])O
Average Molecular Weight434.309
Monoisotopic Molecular Weight434.048525891
Classification
DescriptionThis compound belongs to the class of chemical entities known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassTannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Ellagic_acid
  • Phenolic glycoside
  • 7,8-dihydroxycoumarin
  • O-glycosyl compound
  • Isocoumarin
  • Glycosyl compound
  • Coumarin
  • 2-benzopyran
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0139700000-dc22411162a7333f66ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0159100000-9a473d30387873dcf837View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1092000000-5007766f53152c5bdcf4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-1219700000-67db4997fe588d345b17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1269200000-ea875b68fcc12e05d564View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3091000000-6e948d6982d939f8556cView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID422
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET 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
FoodReference
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 Reference
  1. Mullen W, Yokota T, Lean ME, Crozier A: Analysis of ellagitannins and conjugates of ellagic acid and quercetin in raspberry fruits by LC-MSn. Phytochemistry. 2003 Sep;64(2):617-24. Pubmed [Structure]
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.