6-Oxoibogaine






Names

    • 6-Oxoibogaine

Attributes

  • Canonical SMILES

    CC[C@@H]4C(N(C5)CC3=O)C(C[C@@H]5C4)C2=C3C1=C(N2)C=CC(OC)=C1

  • InChI

    InChI=1S/C20H24N2O2/c1-3-12-6-11-7-15-19-18(17(23)10-22(9-11)20(12)15)14-8-13(24-2)4-5-16(14)21-19/h4-5,8,11-12,15,20-21H,3,6-7,9-10H2,1-2H3/t11-,12-,15?,20?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 45.33
  • #RotBonds: 2
  • MW: 324.42400000000004
  • HBD: 1
  • HBA: 3
  • logP: 3.576800000000002
  • Chemical Formula: C20H24N2O2


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) -4.53
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.86
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.14
    Distribution Blood-Brain Barrier (Central Nervous System) -2.92
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.63
    Plasma Protein Binding 49.01
    Steady State Volume of Distribution 2.93
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor 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 10.67
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.68
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.76
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.77
    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 -2.8
    Rat (Acute) 3.05
    Rat (Chronic Oral) 1.64
    Fathead Minnow 4.12
    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 419.55
    Hydration Free Energy -5.44
    Log(D) at pH=7.4 2.7
    Log(P) 3.36
    Log S -3.28
    Log(Vapor Pressure) -8.29
    Melting Point 224.21
    pKa Acid 7.94
    pKa Basic 7.13