16-Hydroxyibogaine






Names

    • 16-Hydroxyibogaine

Attributes

  • Canonical SMILES

    O[C@]12C3=C(CCN(C4)[C@@]1([H])[C@@H](CC)C[C@]4([H])C2)C5=CC(OC)=CC=C5N3

  • InChI

    InChI=1S/C20H26N2O2/c1-3-13-8-12-10-20(23)18-15(6-7-22(11-12)19(13)20)16-9-14(24-2)4-5-17(16)21-18/h4-5,9,12-13,19,21,23H,3,6-8,10-11H2,1-2H3/t12-,13+,19+,20-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 48.49
  • #RotBonds: 2
  • MW: 326.44
  • HBD: 2
  • HBA: 3
  • logP: 3.0406000000000013
  • Chemical Formula: C20H26N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour. Phytochemistry, 2022 (PMID 35074605).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • α-glucosidase inhibitory
    • Antimicrobial
    • Butyrylcholinesterase

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) -4.99
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.08
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.19
    Distribution Blood-Brain Barrier (Central Nervous System) -2.97
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.48
    Plasma Protein Binding 62.12
    Steady State Volume of Distribution 2.96
    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 12.77
    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 -0.63
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.24
    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 -2.26
    Rat (Acute) 2.61
    Rat (Chronic Oral) 2.22
    Fathead Minnow 3.97
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 427.29
    Hydration Free Energy -6.61
    Log(D) at pH=7.4 2.93
    Log(P) 3.06
    Log S -3.3
    Log(Vapor Pressure) -9.17
    Melting Point 240.69
    pKa Acid 11.06
    pKa Basic 8.52