10,11-Dimethoxy-16-O-methyllisoeburnamenine






Names

    • 10,11-Dimethoxy-16-O-methyllisoeburnamenine

Attributes

  • Canonical SMILES

    COC1=CC2=C(C=C1OC)N3C4=C2CCN5[C@@]4([C@@](CC)(C[C@@H]3OC)C=CC5)[H]

  • InChI

    InChI=1S/C22H28N2O3/c1-5-22-8-6-9-23-10-7-14-15-11-17(25-2)18(26-3)12-16(15)24(19(13-22)27-4)20(14)21(22)23/h6,8,11-12,19,21H,5,7,9-10,13H2,1-4H3/t19-,21-,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 35.86
  • #RotBonds: 4
  • MW: 368.4770000000001
  • HBD: 0
  • HBA: 5
  • logP: 4.072600000000003
  • Chemical Formula: C22H28N2O3


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) -4.85
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.55
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.68
    Distribution Blood-Brain Barrier (Central Nervous System) -2.87
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.93
    Plasma Protein Binding 50.16
    Steady State Volume of Distribution 2.14
    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 Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.29
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.68
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.05
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.39
    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 -13.77
    Rat (Acute) 3.05
    Rat (Chronic Oral) 1.34
    Fathead Minnow 4.33
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 455.01
    Hydration Free Energy -5.95
    Log(D) at pH=7.4 2.92
    Log(P) 3.06
    Log S -2.66
    Log(Vapor Pressure) -7.16
    Melting Point 165.82
    pKa Acid 12.43
    pKa Basic 8.58