Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside (CHEM023944)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:23:13 UTC
Update Date2016-11-09 01:17:48 UTC
Accession NumberCHEM023944
Identification
Common NameIsoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside
ClassSmall Molecule
DescriptionA flavone C-glycoside consisting of luteolin having a beta-D-glucosyl residue at the 6-position.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC21H20O11
Average Molecular Mass448.377 g/mol
Monoisotopic Mass448.101 g/mol
CAS Registry Number496788-50-2
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
Traditional Nameisoorientin
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
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 31V, positivesplash10-001i-0009600000-63aca9b4e94182b5fa78Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 31V, positivesplash10-001i-0007900000-066f6c97856af91728a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0000900000-4deb7298d7dc5928ad89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-3321900000-00aa5483c1d5c8e7a90bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r2-5397200000-4d4fad2cb7e71de05fecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0011900000-17de0eb864f93a041052Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05ds-9336700000-89bd0f817e7ef84d44caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9442000000-e1cf40127250e554e9f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-6cdaf2bc31caca882f1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000900000-6cdaf2bc31caca882f1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0309600000-60823208b2459e4934c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-e34b057bc120eef7d6a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000900000-578e80e06a8f791630d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-0955400000-d57d92c5c589d52431dcSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0301981
FooDB IDFDB001707
Phenol Explorer IDNot Available
KNApSAcK IDC00001055
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsoorientin
Chemspider ID102753
ChEBI ID17965
PubChem Compound ID114776
Kegg Compound IDC01821
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21080643
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22529049
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22948221
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22980875
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23026832
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23220614