Ibogaline






Names

    • 482-18-8
    • DECARBOMETHOXYCONOPHARYNGINE
    • (1R,15R,17S,18S)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene
    • 12,13-Dimethoxyibogamine
    • Ibogamine, 12,13-dimethoxy-
    • (1R,15R,17S,18S)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4,6,8-tetraene
    • DTXCID801391743
    • F9CB5X4DA4
    • Methoxyibogaine
    • 13-METHOXYIBOGAINE
    • DTXSID70964024
    • UNII-F9CB5X4DA4
    • Ibogaline

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C21H28N2O2/c1-4-13-7-12-8-16-20-14(5-6-23(11-12)21(13)16)15-9-18(24-2)19(25-3)10-17(15)22-20/h9-10,12-13,16,21-22H,4-8,11H2,1-3H3/t12-,13+,16+,21+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 37.49
  • #RotBonds: 3
  • MW: 340.46700000000004
  • HBD: 1
  • HBA: 3
  • logP: 3.9452000000000025
  • Chemical Formula: C21H28N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. australis Brazil - ICN-68457
    T. chippii Ivory Coast - Lg12291

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorg Med Chem, 2005 (PMID 15911323).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimicrobial
    • Anticholinesterase

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) -4.72
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.88
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.76
    Distribution Blood-Brain Barrier (Central Nervous System) -3.24
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.6
    Plasma Protein Binding 52.41
    Steady State Volume of Distribution 2.45
    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 9.34
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.39
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.02
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.69
    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 -6.13
    Rat (Acute) 2.89
    Rat (Chronic Oral) 1.63
    Fathead Minnow 4.08
    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 425.01
    Hydration Free Energy -4.33
    Log(D) at pH=7.4 3.2
    Log(P) 2.96
    Log S -3.34
    Log(Vapor Pressure) -7.69
    Melting Point 202.77
    pKa Acid 11.93
    pKa Basic 8.62