Cononusine






Names

    • Cononusine

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)C6CCC(=O)N6

  • InChI

    InChI=1S/C24H31N3O2/c1-3-14-8-13-9-18-23-15(6-7-27(12-13)24(14)18)16-11-21(29-2)17(10-20(16)26-23)19-4-5-22(28)25-19/h10-11,13-14,18-19,24,26H,3-9,12H2,1-2H3,(H,25,28)/t13-,14+,18+,19?,24+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 57.36
  • #RotBonds: 3
  • MW: 393.5310000000001
  • HBD: 2
  • HBA: 3
  • logP: 3.8877000000000024
  • Chemical Formula: C24H31N3O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Ibogan, tacaman, and cytotoxic bisindole alkaloids from tabernaemontana. Cononusine, an iboga alkaloid with unusual incorporation of a pyrrolidone moiety. J Nat Prod, 2015 (PMID 25919190).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Growth inhibitory

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) -4.69
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.18
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.85
    Distribution Blood-Brain Barrier (Central Nervous System) -3.1
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.62
    Plasma Protein Binding 61.12
    Steady State Volume of Distribution 3.56
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-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 8.77
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.18
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.84
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.67
    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 -58.92
    Rat (Acute) 3.12
    Rat (Chronic Oral) 1.62
    Fathead Minnow 4.07
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 496.92
    Hydration Free Energy -3.39
    Log(D) at pH=7.4 2.66
    Log(P) 2.57
    Log S -3.24
    Log(Vapor Pressure) -10.0
    Melting Point 243.26
    pKa Acid 11.51
    pKa Basic 7.63