Voatinggine






Names

    • Voatinggine

Attributes

  • Canonical SMILES

    CC(=O)C1=C[C@H]2C[C@@H](C1)CN3[C@@]24[C@](CC3)(C5=CC=CC=C5N4)O

  • InChI

    InChI=1S/C19H22N2O2/c1-12(22)14-8-13-9-15(10-14)19-18(23,6-7-21(19)11-13)16-4-2-3-5-17(16)20-19/h2-5,10,13,15,20,23H,6-9,11H2,1H3/t13-,15-,18+,19-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 52.57000000000001
  • #RotBonds: 1
  • MW: 310.39699999999993
  • HBD: 2
  • HBA: 4
  • logP: 2.2569000000000004
  • Chemical Formula: C19H22N2O2


Species

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

External Databases


References

  • Voatinggine and tabertinggine, pentacyclic indole alkaloids derived from an iboga precursor via a common cleavamine-type intermediate. Org Lett, 2013 (PMID 23991636).

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) -4.82
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.86
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.32
    Distribution Blood-Brain Barrier (Central Nervous System) -2.55
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.61
    Plasma Protein Binding 49.02
    Steady State Volume of Distribution 3.51
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.9
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.35
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.13
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.66
    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 Safe
    T. Pyriformis -1.34
    Rat (Acute) 3.18
    Rat (Chronic Oral) 2.1
    Fathead Minnow 4.01
    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 388.01
    Hydration Free Energy -6.96
    Log(D) at pH=7.4 1.51
    Log(P) 0.94
    Log S -2.61
    Log(Vapor Pressure) -8.02
    Melting Point 211.21
    pKa Acid 8.56
    pKa Basic 6.31