Record Information
Version1.0
Creation date2010-04-08 22:09:57 UTC
Update date2019-11-26 03:06:01 UTC
Primary IDFDB012030
Secondary Accession Numbers
  • FDB007557
Chemical Information
FooDB NameTaxifolin 3-rhamnoside
DescriptionConstituent of Vitis vinifera (wine grape) Astilbin is a flavanonol, a type of flavonoid. It can be found in St John's wort (Hypericum perforatum, Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in Dimorphandra mollis (Fava d'anta, Fabaceae), in the the leaves of Harungana madagascariensis (Hypericaceae), in the rhizome of Astilbe thunbergii, in the root of Astilbe odontophylla(Saxifragaceae) and in the rhizone of Smilax glabra (Chinaroot, Smilacaceae).
CAS Number29838-67-3
Structure
Thumb
Synonyms
SynonymSource
(2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-oneChEBI
(2R,3R)-3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
Dihydroquercetin-3-O-alpha-lrhapChEBI
(2R,3R)-3-[(6-Deoxy-a-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
(2R,3R)-3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
Dihydroquercetin-3-O-a-lrhapGenerator
Dihydroquercetin-3-O-α-lrhapGenerator
IsoastilbinMeSH
(2R-cis)-Isomer OF astilbinMeSH
3-0-alpha-1-Rhamnosyl-(2R,3R)-dihydroquercetinMeSH
NeoisoastilbinMeSH
(2S-cis)-Isomer OF astilbinMeSH
Astilbindb_source
Taxifolin 3-O-a-L-rhamnopyranosidemanual
Taxifolin 3-O-a-L-rhamnosidemanual
Taxifolin 3-rhamnosidemanual
Predicted Properties
PropertyValueSource
Water Solubility3.64 g/LALOGPS
logP0.79ALOGPS
logP1.09ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)7.74ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.48 m³·mol⁻¹ChemAxon
Polarizability42.86 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H22O11
IUPAC name(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1
InChI KeyZROGCCBNZBKLEL-MPRHSVQHSA-N
Isomeric SMILESC[C@@H]1O[C@@H](O[C@@H]2[C@H](OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
Average Molecular Weight450.3928
Monoisotopic Molecular Weight450.116211546
Classification
Description Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • Flavanonol
  • Flavanone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Flavan
  • Hexose monosaccharide
  • Chromone
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Chromane
  • Aryl alkyl ketone
  • Aryl ketone
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Ether
  • Polyol
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 56.00%; H 4.92%; O 39.08%DFC
Melting PointMp 179-180°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +4 (50% Me2CO aq.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDihydroquercetin 3-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053i-9202300000-af284319f9f7daef6563Spectrum
Predicted GC-MSDihydroquercetin 3-rhamnoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udj-9400018000-46752fa654776148b695Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , negativesplash10-0udj-0931000000-d3051bed4ea8c591959bSpectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0941200000-7752c995c6f2cbdea0b4Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0abi-4973000000-4834cf38b559208d69efSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0339800000-cf9f21b3c745b539fb5dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0967100000-0aa725c6044e8b4d50e4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1921000000-a6239f11b462739244ccSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-2316900000-d0ae694f24bb821e3490Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2938200000-836dd24906777ec601ffSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-3911000000-5af2480f5105a4d92d05Spectrum
NMRNot Available
ChemSpider ID106533
ChEMBL IDCHEMBL486017
KEGG Compound IDC17449
Pubchem Compound ID119258
Pubchem Substance IDNot Available
ChEBI ID38200
Phenol-Explorer ID116
DrugBank IDNot Available
HMDB IDHMDB33850
CRC / DFC (Dictionary of Food Compounds) IDCNL06-P:HCQ85-P
EAFUS IDNot Available
Dr. Duke IDASTILBIN
BIGG IDNot Available
KNApSAcK IDC00008703
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAstilbin
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
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).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— 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.
— 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.