10,11-Dimethoxy-isoeburnamenine






Names

    • 10,11-Dimethoxy-isoeburnamenine

Attributes

  • Canonical SMILES

    COC1=CC2=C(C=C1OC)C3=C4N2[C@@H](O)C[C@](C=CC5)(CC)[C@@]4([H])N5CC3

  • InChI

    InChI=1S/C21H26N2O3/c1-4-21-7-5-8-22-9-6-13-14-10-16(25-2)17(26-3)11-15(14)23(18(24)12-21)19(13)20(21)22/h5,7,10-11,18,20,24H,4,6,8-9,12H2,1-3H3/t18-,20-,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 46.86000000000001
  • #RotBonds: 3
  • MW: 354.45000000000016
  • HBD: 1
  • HBA: 5
  • logP: 3.4185000000000016
  • Chemical Formula: C21H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bovina China, Vietnam 3036760 Cai20150423

External Databases


References

  • Vincan- and eburnan-type alkaloids from Tabernaemontana bovina and their hypoglycemic activity. Phytochemistry, 2021 (PMID 34218044).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Hypoglycemic

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) -4.78
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.71
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.4
    Distribution Blood-Brain Barrier (Central Nervous System) -2.9
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.84
    Plasma Protein Binding 49.62
    Steady State Volume of Distribution 2.0
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.45
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.13
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose None
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.99
    Micronucleos Toxic
    NR-AhR Toxic
    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 -7.37
    Rat (Acute) 2.94
    Rat (Chronic Oral) 1.65
    Fathead Minnow 4.08
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 448.38
    Hydration Free Energy -6.7
    Log(D) at pH=7.4 2.64
    Log(P) 2.47
    Log S -2.38
    Log(Vapor Pressure) -8.02
    Melting Point 199.03
    pKa Acid 11.96
    pKa Basic 7.69