10-Hydroxyibogamine






Names

    • (18R)-ibogamine-12-ol
    • O-desmethylibogaine
    • (1R,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-7-ol
    • PD133273
    • Q7051224
    • (-)-Noribogaine
    • SCHEMBL116220
    • Noribogaine
    • DTXSID90963998
    • 10-Hydroxyibogamine
    • CHEBI:146264

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C19H24N2O/c1-2-12-7-11-8-16-18-14(5-6-21(10-11)19(12)16)15-9-13(22)3-4-17(15)20-18/h3-4,9,11-12,16,19-20,22H,2,5-8,10H2,1H3/t11-,12+,16+,19+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 39.260000000000005
  • #RotBonds: 1
  • MW: 296.41400000000004
  • HBD: 2
  • HBA: 2
  • logP: 3.633600000000002
  • Chemical Formula: C19H24N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. ventricosa Kenya 761103 AM2017/04

External Databases


References

  • Antileishmanial and cytotoxic activity of secondary metabolites from Taberneamontana ventricosa and two aloe species. Nat Prod Res, 2022 (PMID 33459049).

Compound-Protein Relationships


Compound Activities

    • Antileishmanial
    • 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) -4.92
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.09
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.99
    Distribution Blood-Brain Barrier (Central Nervous System) -3.13
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.24
    Plasma Protein Binding 71.97
    Steady State Volume of Distribution 3.99
    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 13.93
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.77
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.92
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.87
    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 -2.12
    Rat (Acute) 2.97
    Rat (Chronic Oral) 1.96
    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 406.0
    Hydration Free Energy -5.04
    Log(D) at pH=7.4 2.7
    Log(P) 2.77
    Log S -3.19
    Log(Vapor Pressure) -8.12
    Melting Point 257.77
    pKa Acid 10.25
    pKa Basic 8.39