19-Epi-iboxygaine






Names

    • 19-Epi-iboxygaine

Attributes

  • Canonical SMILES

    C[C@@H]([C@@]1([H])[C@](N(CCC2=C3NC4=C2C=C(OC)C=C4)C5)([H])C3C[C@@H]5C1)O

  • InChI

    InChI=1S/C20H26N2O2/c1-11(23)15-7-12-8-17-19-14(5-6-22(10-12)20(15)17)16-9-13(24-2)3-4-18(16)21-19/h3-4,9,11-12,15,17,20-21,23H,5-8,10H2,1-2H3/t11-,12-,15-,17?,20+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 48.49
  • #RotBonds: 2
  • MW: 326.44000000000005
  • HBD: 2
  • HBA: 3
  • logP: 2.907400000000002
  • Chemical Formula: C20H26N2O2


Species

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

External Databases


References

  • Dichomine, a novel type of iboga alkaloid*,**. Planta Med, 1983 (PMID 17405059).
  • Tertiary indole alkaloids from leaves of Tabernaemontana dichotoma. Planta Med, 1983 (PMID 17404903).
  • Vobatensines A-F, Cytotoxic Iboga-Vobasine Bisindoles from Tabernaemontana corymbosa. J Nat Prod, 2016 (PMID 26918761).

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) -5.01
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.25
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.11
    Distribution Blood-Brain Barrier (Central Nervous System) -3.19
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.43
    Plasma Protein Binding 53.22
    Steady State Volume of Distribution 3.73
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 11.95
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.64
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.85
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.57
    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 -4.93
    Rat (Acute) 2.94
    Rat (Chronic Oral) 1.85
    Fathead Minnow 4.06
    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 427.02
    Hydration Free Energy -5.75
    Log(D) at pH=7.4 2.15
    Log(P) 2.04
    Log S -2.85
    Log(Vapor Pressure) -8.67
    Melting Point 219.38
    pKa Acid 12.32
    pKa Basic 8.5