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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:40:39 UTC
Update Date2019-07-23 06:23:49 UTC
HMDB IDHMDB0037429
Secondary Accession Numbers
  • HMDB37429
Metabolite Identification
Common NameAstragalin
DescriptionAstragalin 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. Astragalin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Astragalin is found, on average, in the highest concentration within a few different foods, such as yellow wax beans, green beans, and common beans and in a lower concentration in highbush blueberries, common grapes, and american cranberries. Astragalin has also been detected, but not quantified in, several different foods, such as sweet potato, parsley, bilberries, java plums, and docks. This could make astragalin a potential biomarker for the consumption of these foods. A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.
Structure
Data?1563863029
Synonyms
ValueSource
3,4',5,7-Tetrahydroxyflavone-3-glucosideChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-D-glucopyranosideChEBI
AstragalineChEBI
Kaempferol 3-O-glucosideChEBI
Kaempferol-3-O-beta-glucopyranosideChEBI
Kaempferol 3-O-beta-D-glucosideKegg
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl b-D-glucopyranosideGenerator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl β-D-glucopyranosideGenerator
Kaempferol-3-O-b-glucopyranosideGenerator
Kaempferol-3-O-β-glucopyranosideGenerator
Kaempferol 3-O-b-D-glucosideGenerator
Kaempferol 3-O-β-D-glucosideGenerator
3,4',5,7-TetrahydroxyflavoneHMDB
3-O-b-D-GlucopyranosideHMDB
3-O-b-D-Glucopyranosyloxy-4',5,7-trihydroxyflavoneHMDB
AsragalinHMDB
Kaempferol 3-glucosideHMDB
Kaempferol 3-O-beta-D-glucopyranosideHMDB
Kaempferol-3-beta-glucopyranosideHMDB
Kaempferol-3-beta-monoglucosideHMDB
Kaempferol-3-D-glucosideHMDB
Kaempferol-3-glucosideHMDB
Kaempferol-3-O-glucosideHMDB
AstragalinChEBI
Chemical FormulaC21H20O11
Average Molecular Weight448.3769
Monoisotopic Molecular Weight448.100561482
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Nameastragalin
CAS Registry Number480-10-4
SMILES
OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21+/m1/s1
InChI KeyJPUKWEQWGBDDQB-QSOFNFLRSA-N
Chemical Taxonomy
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
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point178 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP0.52ALOGPS
logP0.16ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.29 m³·mol⁻¹ChemAxon
Polarizability42.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8i-8914600000-70416132b3766fd636fbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f72-4730019000-7036585c066b67f1f0ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0iki-0930000000-20176d350f94ae4a84edSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0020900000-182256be3fac5a878f1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090100000-7bd32a5c1969c5a248acSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0560-0090000000-1c2e7f81b693e6297183Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a6r-0090000000-364026dfdcefd0d2e3a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0000900030-4139a6b8a2e916a0ea74Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900000-b3cdd88343725a79c5e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-9834ce03ded5a1fe8c48Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0020900000-182256be3fac5a878f1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090100000-7bd32a5c1969c5a248acSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0560-0090000000-1c2e7f81b693e6297183Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a6r-0090000000-364026dfdcefd0d2e3a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0000900030-4139a6b8a2e916a0ea74Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052b-0090400000-98b6bb6a62f4d8812fdeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0020900010-4e6aa6edffb0c4b2f832Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a59-0090000000-94e191a13790b3b49952Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0000900000-1c8fa629cb5881a42933Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-055b-0090200000-269c7f2460a6f35009c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a7i-0090000000-d43f3a3dfafef985b9efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0190800000-d3b297eb0fe481caa10aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-1e520254d0769f8f845eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-3590000000-7f6360b543570fc55716Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1151900000-879fdf0c200d1a8caf5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1190200000-8b8be60a1a225937d8d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3590000000-22efe60043282fcdf379Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID319
FooDB IDFDB016478
KNApSAcK IDC00005138
Chemspider ID4445311
KEGG Compound IDC12249
BioCyc IDCPD1F-453
BiGG IDNot Available
Wikipedia LinkAstragalin
METLIN IDNot Available
PubChem Compound5282102
PDB IDNot Available
ChEBI ID30200
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .