Astragalin






Names

    • (2S,3S)-DIHYROKAEMPFEROL 3-O-.BETA.-D-GLUCOSIDE', "4',5,7-TRIHYDROXYFLAVONE 3-beta-D-GLUCOPYRANOSIDE", "4',5,7-TRIHYDROXYFLAVONE 3-.BETA.-D-GLUCOPYRANOSIDE", 'KAEMPFEROL 3-O-GLUCOSIDE (CONSTITUENT OF GINKGO) [DSC]
    • Kaempferol-3-beta-monoglucoside
    • Kaempferol 3-O-beta-D-glucoside
    • AKOS015896779
    • cid_5282102
    • s9289
    • BDBM226182
    • GLXC-13293
    • SMR001397194
    • SCHEMBL23897
    • KAEMPFEROL 3-O-beta-GLUCOSIDE
    • 3-O-b-D-Glucopyranoside
    • ZB1884
    • Kaempferol-3-O-glucoside
    • Astragaline;3-Glucosylkaempferol;Kaempferol 3--D-glucopyranoside
    • CS-3720
    • 3-((2S,3R,4S,5S,6R)-
    • Q-100517
    • Kaempferol-3-D-glucoside
    • Kaempferol-3-beta-glucopyranoside', "3,4',5,7-Tetrahydroxyflavone-3-glucoside", 'Kaempferol 3-O-beta-D-glucopyranoside
    • HY-N0015R
    • KAEMPFEROL 3-O-.BETA.-D-GLUCOSIDE
    • (2S,3S)-DIHYROKAEMPFEROL 3-O-beta-D-GLUCOSIDE', "3-O-b-D-Glucopyranosyloxy-4',5,7-trihydroxyflavone", 'BRD-K44487476-001-01-5
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
    • KAEMPFEROL 3-.BETA.-D-GLUCOPYRANOSIDE
    • 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
    • KAEMPFEROL 3-O-.BETA.-GLUCOSIDE
    • MEGxp0_000168
    • Astragaline
    • 3-Glucosylkaempferol
    • HMS2227A14
    • AC-35088
    • BDBM50241243
    • Kaempferol 3-O-.beta.-D-glucopyranoside
    • kaempferol-3-O-D-glucoside
    • NCGC00163580-01
    • Kaempferol 3-glucoside, analytical standard', "3,4'',5,7-Tetrahydroxyflavone-3-glucoside", 'NS00097613
    • Kaempferol 3-O-beta-D-glucoside (6)
    • DTXSID801017739
    • CHEMBL233930
    • Kaempferol 3-|A-D-glucopyranoside
    • KAEMPFEROL 3-O-GLUCOPYRANOSIDE
    • Q4811191
    • HY-N0015
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl .beta.-D-glucopyranoside
    • ACon1_001224
    • DTXCID101475934
    • Kaempferol-3-O-.beta.-D-glucopyranoside
    • Kaempferol 3-O-glucoside
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
    • K5
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
    • kaempferol-3-glucoside
    • 480-10-4
    • Astragalin
    • 4H-1-BENZOPYRAN-4-ONE, 3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-
    • kaempferol-3-O-beta-glucopyranoside
    • KAEMPFEROL 3-O-GLUCOSIDE (CONSTITUENT OF GINKGO)
    • Astragalin (Standard)
    • Astraglin
    • 4H-1-Benzopyran-4-one, 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
    • SR-05000002271-2
    • 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-
    • MLS002473092
    • CHEBI:30200
    • SR-05000002271
    • UNII-APM8UQ3Z9O
    • 3-(beta-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
    • MFCD00075932
    • APM8UQ3Z9O
    • KAEMPFEROL 3-.BETA.-D-GLUCOSIDE
    • Kaempferol 3-beta-D-glucopyranoside, >=97.0% (HPLC)
    • KAEMPFEROL 3-beta-D-GLUCOSIDE
    • asragalin
    • Kaempferol 3-glucoside
    • Astragalin?
    • CCG-269212
    • Kaempferol 3-beta-D-glucopyranoside
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-D-glucopyranoside
    • NCGC00163580-02
    • Kaempferol 3-glucoside, primary pharmaceutical reference standard

Attributes

  • Canonical SMILES

    C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O

  • InChI

    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

  • Molecule Class: Flavonoids
  • TPSA: 190.27999999999997
  • #RotBonds: 4
  • MW: 448.3800000000001
  • HBD: 7
  • HBA: 11
  • logP: -0.24450000000000044
  • Chemical Formula: C21H20O11


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. pandacaqui Cuba, Thailand 761085 -

External Databases


References

  • Acetylcholinesterase Inhibitor From Tabernaemontana pandacaqui Flowers Natural Product Communications, 2020 (DOI).

Compound-Protein Relationships


Compound Activities

    • Acetylcholinesterase inhibitory

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.

Predicted ADMET Properties

    Property Model Name Predicted Value
    Absorption Caco-2 (logPaap) -6.33
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney -5.54
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability 1.73
    Distribution Blood-Brain Barrier (Central Nervous System) -4.23
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.9
    Plasma Protein Binding 82.18
    Steady State Volume of Distribution 1.01
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.65
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Safe
    Bioconcentration Factor -1.92
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 1.08
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.6
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -74.15
    Rat (Acute) 2.42
    Rat (Chronic Oral) 3.73
    Fathead Minnow 3.92
    Respiratory Disease Safe
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 605.22
    Hydration Free Energy -5.34
    Log(D) at pH=7.4 0.4
    Log(P) 0.98
    Log S -4.19
    Log(Vapor Pressure) -11.53
    Melting Point 212.24
    pKa Acid 5.76
    pKa Basic 7.09