Sinapic acid-hexoside






Names

    • (E)-3-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
    • CHEMBL3916405
    • AKOS040736221
    • (2E)-3-[4-(beta-D-glucopyranosyloxy)-3,5-dimethoxyphenyl]acrylic acid
    • CHEBI:145341
    • Sinapic acid-hexoside
    • O(4)-(beta-D-glucosyl)-(2E)-sinapic acid
    • sinapoyl-4-O-beta-D-glucoside
    • trans-p-Sinapoyl-I(2)-D-glucopyranoside
    • 117405-52-4
    • Sinapic acid O-glucoside
    • 4-O-beta-D-glucosyl-trans-sinapic acid
    • 4-O-(beta-D-glucosyl)-(2E)-sinapic acid
    • 2-Propenoic acid, 3-[4-(beta-D-glucopyranosyloxy)-3,5-dimethoxyphenyl]-, (2E)-', "4'-O-Glucopyranosylsinapic acid", 'C02919
    • 4-O-(beta-D-glucopyranosyl)-(2E)-sinapic acid
    • DTXSID801291032

Attributes

  • Canonical SMILES

    [H]O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1O[H])OC2=C(C=C(C=C2OC)/C=C/C(O[H])=O)OC)CO[H])O[H]

  • InChI

    InChI=1S/C17H22O10/c1-24-9-5-8(3-4-12(19)20)6-10(25-2)16(9)27-17-15(23)14(22)13(21)11(7-18)26-17/h3-6,11,13-15,17-18,21-23H,7H2,1-2H3,(H,19,20)/b4-3+/t11-,13-,14+,15-,17+/m1/s1

  • Molecule Class: Flavonoids
  • TPSA: 155.14000000000001
  • #RotBonds: 7
  • MW: 386.3530000000001
  • HBD: 5
  • HBA: 9
  • logP: -1.0196999999999998
  • Chemical Formula: C17H22O10


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. heyneana India 2563820 -

External Databases


References

  • Simultaneous Extraction Optimization and Analysis of Flavonoids from the Flowers of Tabernaemontana heyneana by High Performance Liquid Chromatography Coupled to Diode Array Detector and Electron Spray Ionization/Mass Spectrometry. ISRN Biotechnol, 2013 (PMID 25969771).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antithrombogenic
    • Antiviral
    • Antimicrobial
    • Antioxidant
    • Antihypercholesterolemic

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) -6.04
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.01
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.54
    Distribution Blood-Brain Barrier (Central Nervous System) -4.21
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.89
    Plasma Protein Binding 71.08
    Steady State Volume of Distribution 0.46
    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 6.86
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life >= 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.63
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.85
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.88
    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 -4.54
    Rat (Acute) 1.8
    Rat (Chronic Oral) 3.45
    Fathead Minnow 4.17
    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 462.62
    Hydration Free Energy -15.83
    Log(D) at pH=7.4 -1.74
    Log(P) -0.51
    Log S -2.19
    Log(Vapor Pressure) -11.92
    Melting Point 172.74
    pKa Acid 3.89
    pKa Basic 4.05