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Showing Compound Astragalin (FDB016478)

Record Information
Version1.0
Creation date2010-04-08 22:12:27 UTC
Update date2019-11-26 03:13:18 UTC
Primary IDFDB016478
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). Astragalin is found, on average, in the highest concentration in a few different foods, such as yellow wax beans, green beans, and common beans and in a lower concentration in highbush blueberries, blackcurrants, and quinces. Astragalin has also been detected, but not quantified in, several different foods, such as shea tree, lemon thymes, groundcherries, wax gourds, and wasabis. This could make astragalin a potential biomarker for the consumption of these foods.
CAS Number480-10-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
3,4',5,7-Tetrahydroxyflavone; 3-O-b-D-Glucopyranosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP0.52ALOGPS
logP0.16ChemAxon
logS-2.5ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O11
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
InChI IdentifierInChI=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
Isomeric SMILESOC[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
Average Molecular Weight448.3769
Monoisotopic Molecular Weight448.100561482
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
  • 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:

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 178°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]18D +16.9 (c, 0.62 in MeOH)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, Positivesplash10-0f8i-8914600000-70416132b3766fd636fbJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f72-4730019000-7036585c066b67f1f0ceJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0iki-0930000000-20176d350f94ae4a84edJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0020900000-182256be3fac5a878f1bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090100000-7bd32a5c1969c5a248acJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0560-0090000000-1c2e7f81b693e6297183JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a6r-0090000000-364026dfdcefd0d2e3a9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0000900030-4139a6b8a2e916a0ea74JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900000-b3cdd88343725a79c5e0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-9834ce03ded5a1fe8c48JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0020900000-182256be3fac5a878f1bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090100000-7bd32a5c1969c5a248acJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0560-0090000000-1c2e7f81b693e6297183JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a6r-0090000000-364026dfdcefd0d2e3a9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0000900030-4139a6b8a2e916a0ea74JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052b-0090400000-98b6bb6a62f4d8812fdeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0020900010-4e6aa6edffb0c4b2f832JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a59-0090000000-94e191a13790b3b49952JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0000900000-1c8fa629cb5881a42933JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-055b-0090200000-269c7f2460a6f35009c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a7i-0090000000-d43f3a3dfafef985b9efJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0190800000-d3b297eb0fe481caa10aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-1e520254d0769f8f845eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-3590000000-7f6360b543570fc55716JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1151900000-879fdf0c200d1a8caf5bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1190200000-8b8be60a1a225937d8d8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3590000000-22efe60043282fcdf379JSpectraViewer
ChemSpider ID4445311
ChEMBL IDNot Available
KEGG Compound IDC12249
Pubchem Compound ID5282102
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID319
DrugBank IDNot Available
HMDB IDHMDB37429
CRC / DFC (Dictionary of Food Compounds) IDKRH29-Q:KRH29-Q
EAFUS IDNot Available
Dr. Duke IDASTRAGALIN|KAEMPFEROL-3-O-GLUCOSIDE|KAEMPFEROL-3-O-BETA-D-GLUCOSIDE|KAEMPFEROL-3-MONOGLUCOSIDE|KAEMPFEROL-3-BETA-D-GLUCOSIDE|KAEMPFEROL-3-0-GLUCOSIDE|3-O-BETA-D-KAEMPFEROL-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00005138
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAstragalin
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
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
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
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cholereticDUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
hypotensiveDUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.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).
— 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.