Iboxygaine






Names

    • (1S)-1-[(1R,15S,17R,18R)-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-17-yl]ethanol
    • Kimvuline
    • DTXSID90231508
    • Iboxygaine
    • (1S)-1-((1R,15S,17R,18R)-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraen-17-yl)ethanol
    • Ibogamin-20-ol, 12-methoxy-, (4alpha,20S)-
    • (4alpha)-12-Methoxyibogamin-20S-ol
    • DTXCID50153999
    • 82-55-3
    • (-)-Iboxygaine

Attributes

  • Canonical SMILES

    C[C@@H]([C@@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)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: 326.44
  • HBD: 2
  • HBA: 3
  • logP: 2.9074000000000013
  • Chemical Formula: C20H26N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. laeta Brazil 761076 WAG

External Databases


References

  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc, 2008 (PMID 18797794).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity
    • Acetylbutyrylcholinesterase 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) -5.11
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.27
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.15
    Distribution Blood-Brain Barrier (Central Nervous System) -3.24
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.42
    Plasma Protein Binding 61.95
    Steady State Volume of Distribution 3.76
    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 12.07
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.54
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.88
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.54
    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 -4.94
    Rat (Acute) 2.96
    Rat (Chronic Oral) 1.86
    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 427.17
    Hydration Free Energy -5.69
    Log(D) at pH=7.4 2.12
    Log(P) 1.94
    Log S -2.86
    Log(Vapor Pressure) -8.77
    Melting Point 225.96
    pKa Acid 12.36
    pKa Basic 8.4