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Showing Compound Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside (FDB001707)

Record Information
Version1.0
Creation date2010-04-08 22:05:05 UTC
Update date2025-11-18 22:32:37 UTC
Primary IDFDB001707
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside
DescriptionIsoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside, also known as homoorientin or luteolin-6-C-beta-D-glucoside, is a member of the class of compounds known as flavonoid c-glycosides. Flavonoid c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside can be synthesized from luteolin. Isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside is also a parent compound for other transformation products, including but not limited to, isoorientin 7-O-glucoside, 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucosyl]isoorientin, and 7-O-(6-sinapoylglucosyl)isoorientin. Isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside can be found in barley, which makes isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside a potential biomarker for the consumption of this food product.
CAS Number496788-50-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-6-beta-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
HomoorientinChEBI
Luteolin-6-C-beta-D-glucosideChEBI
2-(3,4-Dihydroxyphenyl)-6-b-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
Luteolin-6-C-b-D-glucosideGenerator
Luteolin-6-C-β-D-glucosideGenerator
6-GLC-LuteolinMeSH
Iso-orientinMeSH
Luteolin-6-C-glucosideMeSH
Predicted Properties
PropertyValueSource
logP-0.35ChemAxon
pKa (Strongest Acidic)6.14ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area197.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity108.01 m³·mol⁻¹ChemAxon
Polarizability42.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H20O11
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21+/m1/s1
InChI KeyODBRNZZJSYPIDI-VJXVFPJBSA-N
Isomeric SMILESOC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC(O)=C(O)C=C2)C=C1O
Average Molecular Weight448.3769
Monoisotopic Molecular Weight448.100561482
Classification
Description Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid C-glycosides
Alternative Parents
Substituents
  • Flavonoid c-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • C-glycosyl compound
  • Glycosyl compound
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 31V, positivesplash10-001i-0009600000-63aca9b4e94182b5fa782020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 31V, positivesplash10-001i-0007900000-066f6c97856af91728a52020-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0000900000-4deb7298d7dc5928ad892016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-3321900000-00aa5483c1d5c8e7a90b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r2-5397200000-4d4fad2cb7e71de05fec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0011900000-17de0eb864f93a0410522016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05ds-9336700000-89bd0f817e7ef84d44ca2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9442000000-e1cf40127250e554e9f22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-6cdaf2bc31caca882f1d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000900000-6cdaf2bc31caca882f1d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0309600000-60823208b2459e4934c52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-e34b057bc120eef7d6a02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000900000-578e80e06a8f791630d82021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-0955400000-d57d92c5c589d52431dc2021-10-21View Spectrum
NMRNot Available
ChemSpider ID102753
ChEMBL IDCHEMBL239559
KEGG Compound IDC01821
Pubchem Compound ID114776
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 IDISOORIENTIN-7-FERULYL-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00014097
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDIsoorientin
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.