Back to Compounds

Showing Compound Astragalin (FDB016478)

Record Information
Version1.0
Creation date2010-04-08 22:12:27 UTC
Update date2020-09-17 15:36:58 UTC
Primary IDFDB016478
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAstragalin
DescriptionKaempferol 3-O-beta-D-glucoside also known as astragalin, is a kaempferol O-glucoside in which the glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage. Astragalin has been isolated from many different plants and plant families including members of the Fabaceae, Convolvulaceae, Ebenaceae, Rosaceae and Eucommiaceae families. This compound is well known for its diverse pharmacological applications such as anti-inflammatory, antioxidant, neuroprotective, cardioprotective, antiobesity, antiosteoporotic, anticancer, antiulcer, and antidiabetic properties (PMID: 29853868). It appears to carry out these activities by the regulation and modulation of various molecular targets such as transcription factors (NF-κB, TNF-α, and TGF-β1), enzymes (iNOS, COX-2, PGE2, MMP-1, MMP-3, MIP-1α, COX-2, PGE-2, HK2, AChe, SOD, DRP-1, DDH, PLCŒ≥1, and GPX), kinases (JNK, MAPK, Akt, ERK, SAPK, IκBα, PI3K, and PKCβ2), cell adhesion proteins (E-cadherin, vimentin PAR-2, and NCam), apoptotic and antiapoptotic proteins (Beclin-1, Bcl-2, Bax, Bcl-xL, cytochrome c, LC3A/B, caspase-3, caspase-9, procaspase-3, procaspase-8, and IgE), and inflammatory cytokines (SOCS-3, SOCS-5, IL-1β, IL-4, IL-6, IL-8, IL-13, MCP-1, CXCL-1, CXCL-2, and IFN-γ) (PMID: 29853868).
CAS Number480-10-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
Kaempferol 3-O-beta-D-glucopyranosideMeSH
AstragalinChEBI
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-beta-glucopyranosideHMDB
Kaempferol-3-beta-monoglucosideHMDB
Kaempferol-3-D-glucosideHMDB
Kaempferol-3-glucosideHMDB
Kaempferol-3-O-glucosideHMDB
3-GlucosylkaempferolPhytoBank
4',5,7-Trihydroxyflavone 3-beta-D-glucopyranosidePhytoBank
4',5,7-Trihydroxyflavone 3-β-D-glucopyranosidePhytoBank
4’,5,7-Trihydroxyflavone 3-β-D-glucopyranosidePhytoBank
Kaemferol 3-O-glucopyranosidePhytoBank
Kaempferol 3-O-glucopyranosidePhytoBank
Kaempferol 3-O-β-D-glucopyranosidePhytoBank
Kaempferol 3-O-beta-glucosidePhytoBank
Kaempferol 3-O-β-glucosidePhytoBank
Kaempferol 3-beta-D-glucopyranosidePhytoBank
Kaempferol 3-β-D-glucopyranosidePhytoBank
Kaempferol 3-beta-D-glucosidePhytoBank
Kaempferol 3-β-D-glucosidePhytoBank
Kaempherol 3-O-beta-D-glucopyranosidePhytoBank
Kaempherol 3-O-β-D-glucopyranosidePhytoBank
3,4',5,7-Tetrahydroxyflavone; 3-O-b-D-Glucopyranosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP0.52ALOGPS
logP0.16ChemAxon
logS-2.4ALOGPS
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
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAstragalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f8i-8914600000-70416132b3766fd636fbSpectrum
Predicted GC-MSAstragalin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f72-4730019000-7036585c066b67f1f0ceSpectrum
Predicted GC-MSAstragalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0iki-0930000000-20176d350f94ae4a84ed2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0020900000-182256be3fac5a878f1b2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090100000-7bd32a5c1969c5a248ac2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0560-0090000000-1c2e7f81b693e62971832017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a6r-0090000000-364026dfdcefd0d2e3a92017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0000900030-4139a6b8a2e916a0ea742017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900000-b3cdd88343725a79c5e02017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-9834ce03ded5a1fe8c482017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0020900000-182256be3fac5a878f1b2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090100000-7bd32a5c1969c5a248ac2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0560-0090000000-1c2e7f81b693e62971832017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a6r-0090000000-364026dfdcefd0d2e3a92017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0000900030-4139a6b8a2e916a0ea742017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052b-0090400000-98b6bb6a62f4d8812fde2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0020900010-4e6aa6edffb0c4b2f8322017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a59-0090000000-94e191a13790b3b499522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0000900000-1c8fa629cb5881a429332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-055b-0090200000-269c7f2460a6f35009c82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a7i-0090000000-d43f3a3dfafef985b9ef2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0190800000-d3b297eb0fe481caa10a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-1e520254d0769f8f845e2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-3590000000-7f6360b543570fc557162016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1151900000-879fdf0c200d1a8caf5b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1190200000-8b8be60a1a225937d8d82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3590000000-22efe60043282fcdf3792016-08-03View Spectrum
NMRNot Available
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 agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.DUKE
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
CholereticAn agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.DUKE
Expectorant52217 An agent that thins and loosens mucus, making it easier to cough up, reducing congestion. It aids in clearing respiratory tract secretions, commonly used to relieve coughs, colds, and bronchitis, promoting easier breathing and soothing irritated airways.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.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.