Taberyunine E






Names

    • Taberyunine E

Attributes

  • Canonical SMILES

    C(C)[C@@]12[C@]3([C@@]4(C(=C(C(OC)=O)C1)NC=5C4=CC=C(OC)C5)CCN3[C@@H]([C@@]6([C@]2(O6)[H])[H])C=7C=C8[C@@]9%10[C@@]%11([C@@](CC)([C@]%12([C@@](CN%11CC9)(O%12)[H])[H])CC[C@@]%10(N(C)C8=CC7)[H])[H])[H]

  • InChI

    InChI=1S/C42H50N4O5/c1-6-39-13-12-30-41(14-16-45(37(39)41)21-29-34(39)50-29)26-18-22(8-11-28(26)44(30)3)31-32-35(51-32)40(7-2)20-24(36(47)49-5)33-42(15-17-46(31)38(40)42)25-10-9-23(48-4)19-27(25)43-33/h8-11,18-19,29-32,34-35,37-38,43H,6-7,12-17,20-21H2,1-5H3/t29-,30+,31-,32-,34-,35-,37+,38+,39-,40-,41+,42+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 82.34
  • #RotBonds: 5
  • MW: 690.8849999999999
  • HBD: 1
  • HBA: 9
  • logP: 5.284000000000005
  • Chemical Formula: C42H50N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Trimeric and dimeric Aspidosperma-type alkaloids from leaves of Tabernaemontana divaricata 'Dwaft'. Bioorg Chem, 2021 (PMID 34500306).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity

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) -5.3
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 30.43
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 4695.06
    Distribution Blood-Brain Barrier (Central Nervous System) -2.99
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.1
    Plasma Protein Binding 57.69
    Steady State Volume of Distribution 2.86
    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 Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.66
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -114.07
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.95
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 6.66
    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 Toxic
    T. Pyriformis -8524286.11
    Rat (Acute) 3.03
    Rat (Chronic Oral) 1.46
    Fathead Minnow 10760.14
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 956050.45
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.54
    Log(P) 4.32
    Log S -5.03
    Log(Vapor Pressure) -31374.64
    Melting Point 201.98
    pKa Acid -191.09
    pKa Basic 8.06