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Showing Compound Apigenin 6-C-arabinoside 8-C-glucoside (FDB000136)

Record Information
Version1.0
Creation date2010-04-08 22:04:27 UTC
Update date2019-11-26 02:54:32 UTC
Primary IDFDB000136
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameApigenin 6-C-arabinoside 8-C-glucoside
DescriptionApigenin 6-c-arabinoside 8-c-glucoside is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Apigenin 6-c-arabinoside 8-c-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Apigenin 6-c-arabinoside 8-c-glucoside can be found in common wheat, which makes apigenin 6-c-arabinoside 8-c-glucoside a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility6.44 g/LALOGPS
logP-0.7ALOGPS
logP-2.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)5.76ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area247.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity133.19 m³·mol⁻¹ChemAxon
Polarizability54.51 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC26H28O14
IUPAC name6-[(3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
InChI IdentifierInChI=1S/C26H28O14/c27-6-12-17(31)21(35)23(37)26(40-12)16-20(34)15(25-22(36)18(32)13(7-28)39-25)19(33)14-10(30)5-11(38-24(14)16)8-1-3-9(29)4-2-8/h1-5,12-13,17-18,21-23,25-29,31-37H,6-7H2/t12-,13+,17-,18+,21+,22-,23-,25?,26?/m1/s1
InChI KeyDRLZZQRQMWQRLZ-FBMRRHFKSA-N
Isomeric SMILESOC[C@@H]1OC([C@H](O)[C@H]1O)C1=C(O)C(C2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1
Average Molecular Weight564.4921
Monoisotopic Molecular Weight564.147905604
Classification
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Glycosyl compound
  • Chromone
  • C-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Tetrahydrofuran
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Dialkyl ether
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0000490000-7b85c9efde7045dc11502016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1400290000-4fb98ede80290a3baa082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-1109710000-e3b71f5e478d20c38b112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1000390000-93d6ee328d2b08869c6a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vn-6400890000-b04dc9a57a52b9edab302016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k96-9401710000-aa2523d22854b0be52942016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-2b44d7c7097dece6794d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000090000-2b44d7c7097dece6794d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0401960000-093631fb2a5b6ffdabea2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-7dac33c1867ebf2369b92021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000090000-5d8a4e28f213bae4d1382021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-0900630000-d29e083ca2321a32cc9a2021-10-21View 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 ID249
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 ReferenceNot Available
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.