Record Information
Version1.0
Creation date2010-04-08 22:05:24 UTC
Update date2020-02-24 19:10:31 UTC
Primary IDFDB002510
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameOrientin
DescriptionOrientin, also known as lutexin, 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. Orientin is an extremely weak basic (essentially neutral) compound (based on its pKa). Orientin has been detected, but not quantified in, several different foods, such as flaxseeds, rices, common salsifies, oats, and highbush blueberries. This could make orientin a potential biomarker for the consumption of these foods.
CAS Number28608-75-5
Structure
Thumb
Synonyms
SynonymSource
8-b-D-Glucopyranosyl-3',4',5,7-tetrahydroxyflavoneHMDB
8-b-D-GlucopyranosylluteolinHMDB
8-beta-D-GlucosylluteolinHMDB
8-GlucosylluteolinHMDB
Luteolin 8-C-beta-D-glucopyranosideHMDB
Luteolin 8-C-glucosideHMDB
Luteolin 8-glucosideHMDB
Luteolin-8-glucosideHMDB
LutexinHMDB
8-C-beta-Glucopyranosyl-3',4',5,7-tetrahydroxyflav-2-en-3-oneMeSH
Luteolin-8-c-glucosideMeSH
OrientinMeSH
OrientineMeSH
8-beta-D-glucosylluteolinbiospider
Predicted Properties
PropertyValueSource
Water Solubility2.18 g/LALOGPS
logP0.34ALOGPS
logP-0.35ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)6.2ChemAxon
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
Polarizability42.33 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O11
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2
InChI KeyPLAPMLGJVGLZOV-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(C(O)C(O)C1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC(O)=C(O)C=C1
Average Molecular Weight448.3769
Monoisotopic Molecular Weight448.100561482
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
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • C-glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • Phenol
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.25%; H 4.50%; O 39.25%DFC
Melting PointMp 265-267° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +18.4 (c, 1.4 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-5359500000-f9adac53dffd9a9c99e7JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udm-2400649000-74ca092951d9881de08bJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004j-0009400000-3059cfe62dc1fc2d4ae7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-002b-0139400000-f3fff996fce68da266cbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0000900000-dbaba69a1ec2e196894cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-3321900000-58f0bdc82c44d422ce9bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bta-4298000000-6aa6da44ac805b909faeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0011900000-11759d86677ab5572af7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bj-8348900000-5afe26ef74613ffacf3cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9443000000-3dafb42d1ba4e7e09433JSpectraViewer
ChemSpider ID4529887
ChEMBL IDNot Available
KEGG Compound IDC10114
Pubchem Compound ID5382105
Pubchem Substance IDNot Available
ChEBI ID7781
Phenol-Explorer ID255
DrugBank IDNot Available
HMDB IDHMDB30614
CRC / DFC (Dictionary of Food Compounds) IDCMF48-S:CMF48-S
EAFUS IDNot Available
Dr. Duke IDORIENTIN
BIGG IDNot Available
KNApSAcK IDC00001078
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDOrientin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
cAMP-phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).