19,20-Epoxyconoduramine






Names

    • 19,20-Epoxyconoduramine

Attributes

  • Canonical SMILES

    C[C@@H]1CC(C2=C(C=CC=C2)N3)=C3[C@](C4=C(C=C(C5=C4)NC6C5[N@]7C[C@@H]8C[C@@](C(OC)=O)(CC6)[C@]7([H])[C@H](CC)C8)OC)([H])C[C@@H](CC(OC)=O)[C@]9(O[C@@H]9C)CN1C

  • InChI

    InChI=1S/C44H58N4O6/c1-8-27-16-26-21-43(42(50)53-7)14-13-35-40(48(22-26)41(27)43)33-19-30(37(51-5)20-36(33)45-35)32-17-28(18-38(49)52-6)44(25(3)54-44)23-47(4)24(2)15-31-29-11-9-10-12-34(29)46-39(31)32/h9-12,19-20,24-28,32,35,40-41,45-46H,8,13-18,21-23H2,1-7H3/t24-,25-,26+,27-,28+,32-,35?,40?,41+,43+,44+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 108.66000000000001
  • #RotBonds: 6
  • MW: 738.97
  • HBD: 2
  • HBA: 9
  • logP: 6.820500000000008
  • Chemical Formula: C44H58N4O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. johnstonii Kenya - -

External Databases


References

  • Plant anticancer agents V: new bisindole alkaloids from Tabernaemontana johnstonii stem bark. J Pharm Sci, 1978 (PMID 621649).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity
    • Reproducible
    • Antileukemic
    • Anticancer

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) -5.47
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 38.27
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 5741.07
    Distribution Blood-Brain Barrier (Central Nervous System) -3.07
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.22
    Plasma Protein Binding 66.74
    Steady State Volume of Distribution 3.21
    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 Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 10.0
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -137.73
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.29
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 6.08
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Toxic
    T. Pyriformis -10421355.89
    Rat (Acute) 2.87
    Rat (Chronic Oral) 1.57
    Fathead Minnow 13158.45
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 1168876.55
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.57
    Log(P) 6.21
    Log S -4.97
    Log(Vapor Pressure) -38407.78
    Melting Point 223.37
    pKa Acid -233.23
    pKa Basic 8.13