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Ellagic acid acetyl-arabinoside (FDB000225)

Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2019-11-26 02:54:34 UTC
Primary IDFDB000225
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEllagic acid acetyl-arabinoside
DescriptionEllagic acid acetyl-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 acetyl-arabinoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Ellagic acid acetyl-arabinoside can be found in red raspberry, which makes ellagic acid acetyl-arabinoside a potential biomarker for the consumption of this food product.
CAS Number476-66-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.13 g/LALOGPS
logP1.44ALOGPS
logP1.12ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.83ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area198.51 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.94 m³·mol⁻¹ChemAxon
Polarizability43.09 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H16O13
IUPAC name(3S,4R,5R,6S)-4,5-dihydroxy-6-({7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaen-6-yl}oxy)oxan-3-yl acetate
InChI IdentifierInChI=1S/C21H16O13/c1-5(22)31-10-4-30-21(16(27)14(10)25)32-9-3-7-12-11-6(19(28)34-18(12)15(9)26)2-8(23)13(24)17(11)33-20(7)29/h2-3,10,14,16,21,23-27H,4H2,1H3/t10-,14-,16+,21-/m0/s1
InChI KeyHRUPKKAITRRGMV-GLEFEWGCSA-N
Isomeric SMILESCC(=O)O[C@H]1CO[C@@H](OC2=CC3=C4C(OC(=O)C5=CC(O)=C(O)C(OC3=O)=C45)=C2O)[C@H](O)[C@H]1O
Average Molecular Weight476.3439
Monoisotopic Molecular Weight476.059090598
Classification
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Ellagic_acid
  • Phenolic glycoside
  • 7,8-dihydroxycoumarin
  • Coumarin
  • Glycosyl compound
  • Isocoumarin
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 2-benzopyran
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Lactone
  • Oxacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1128900000-2593ae55f4b3b337f8bb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0149100000-b0230d5af3b38db936ff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2293000000-ea660cfabb1ead03a8b82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pe9-5314900000-b9552d86931bae7948da2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9147400000-5e8f5d5f67018b7e6a732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9041000000-66b65c4af0fe35f3f8172016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009600000-be3ccbec6353a2cc46852021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0019200000-1e0e4e310df3e15a5e682021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hg6-9737100000-309d407805006c23f0152021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0003900000-e3258256f26e03afe0c62021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-5149000000-6f4a7698c8819d2221d12021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9051100000-efab20f817b43eef57312021-10-21View 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 ID424
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
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
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
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.