Record Information
Version1.0
Creation date2010-04-08 22:12:27 UTC
Update date2019-11-26 03:13:16 UTC
Primary IDFDB016454
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDiosmetin 3,8-di-C-glucoside
Description3,8-Diglucosyldiosmetin 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. 3,8-Diglucosyldiosmetin is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,8-Diglucosyldiosmetin has been detected, but not quantified in, citrus and sweet oranges. This could make 3,8-diglucosyldiosmetin a potential biomarker for the consumption of these foods.
CAS Number97218-32-1
Structure
Thumb
Synonyms
SynonymSource
3,8-Di-C-glucopyranosyldiosmetinHMDB
3,8-Diglucopyranosyl-3',5,7-trihydroxy-4'-methoxyflavoneHMDB
3,8-DiglucopyranosyldiosmetinHMDB
3,8-Diglucosyldiosmetindb_source
Diosmetin 3,8-di-C-glucosidemanual
Predicted Properties
PropertyValueSource
Water Solubility7.54 g/LALOGPS
logP-0.93ALOGPS
logP-3.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)6.14ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area276.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity144.93 m³·mol⁻¹ChemAxon
Polarizability59.01 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H32O16
IUPAC name5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
InChI IdentifierInChI=1S/C28H32O16/c1-41-12-3-2-8(4-9(12)31)25-17(28-24(40)22(38)19(35)14(7-30)43-28)20(36)15-10(32)5-11(33)16(26(15)44-25)27-23(39)21(37)18(34)13(6-29)42-27/h2-5,13-14,18-19,21-24,27-35,37-40H,6-7H2,1H3
InChI KeyOZSVEJJFZRCNON-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=C(C=C1)C1=C(C2OC(CO)C(O)C(O)C2O)C(=O)C2=C(O1)C(C1OC(CO)C(O)C(O)C1O)=C(O)C=C2O
Average Molecular Weight624.5441
Monoisotopic Molecular Weight624.169034976
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
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • C-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Polyol
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.85%; H 5.16%; O 40.99%DFC
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-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06sl-1000191000-29af48a161274b058de3Spectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_1_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiosmetin 3,8-di-C-glucoside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0000129000-1e511bfe0c0cd1b05da5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2300498000-020de5a95523ed5321b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-1003930000-2c4108daab6aeb2cdd58Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000249000-054908f9b5a6a4ba87cdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kn9-3000393000-600254964cccd9b27ca9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-4103390000-494ddec8d63fd5fcd1e7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000009000-6e37f976b9b174b76115Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000009000-6e37f976b9b174b76115Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w29-0019001000-1733530a9bf0bfd54ba9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-2d7dfb6c8050c5654c90Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000009000-2d7dfb6c8050c5654c90Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-0019004000-c6555f429dc532c754dfSpectrum
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 IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37409
CRC / DFC (Dictionary of Food Compounds) IDKRG20-C:KRG21-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00006287
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.