Ibogamine






Names

    • CHEBI:5853
    • Q5984343
    • (-)-ibogamine
    • 481-87-8
    • SCHEMBL433382
    • (1R,15R,17S,18S)-17-Ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene
    • Ibogamine
    • BDBM50597222
    • CHEMBL5184088
    • NSC 267705

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C19H24N2/c1-2-13-9-12-10-16-18-15(7-8-21(11-12)19(13)16)14-5-3-4-6-17(14)20-18/h3-6,12-13,16,19-20H,2,7-11H2,1H3/t12-,13+,16+,19+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 19.03
  • #RotBonds: 1
  • MW: 280.41499999999996
  • HBD: 1
  • HBA: 1
  • logP: 3.9280000000000026
  • Chemical Formula: C19H24N2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. alba Mexico 761051 132793, 133359, 161424 to 161427
    T. arborea Mexico, Costa Rica 681494 132793, 133359, 161424 to 161427
    T. australis Brazil - ICN-68457
    T. bufalina China 403123 Cai20170220
    T. calcarea Madagascar 761054 -
    T. catharinensis Brazil 403124 UEC117862
    T. corymbosa Malaysia, China 1679252 GK604
    T. dichotoma Sri Lanka, Malaysia - -
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. laeta Brazil 761076 WAG
    T. officinalis China - Cai20120227
    T. ventricosa Kenya 761103 AM2017/04

External Databases


References

  • Taberdines L and M, two new alkaloids from Tabernaemontana divaricata. Nat Prod Res, 2022 (PMID 34933610).
  • Quantification of Anti-Addictive Alkaloids Ibogaine and Voacangine in In Vivo- and In Vitro-Grown Plants of Two Mexican Tabernaemontana Species. Chem Biodivers, 2016 (PMID 27448833).
  • New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest. J Nat Prod, 2003 (PMID 12713407).
  • Bio-guided search of active indole alkaloids from Tabernaemontana catharinensis: Antitumour activity, toxicity in silico and molecular modelling studies. Bioorg Chem, 2019 (PMID 30599414).
  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).
  • Virtual Screening of compounds from Tabernaemontana divaricata for potential anti-bacterial activity. Bioinformation, 2014 (PMID 24748755).
  • 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).
  • Antimycobacterial Activity of Alkaloids and Extracts from Tabernaemontana alba and T. arborea. Planta Med, 2022 (PMID 32392600).
  • Antileishmanial and cytotoxic activity of secondary metabolites from Taberneamontana ventricosa and two aloe species. Nat Prod Res, 2022 (PMID 33459049).
  • Tertiary indole alkaloids of Tabernaemontana dichotoma seeds. Planta Med, 1983 (PMID 6635015).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorg Med Chem, 2005 (PMID 15911323).
  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).
  • Central nervous system activity of a Tabernaemontana arborea alkaloid extract involves serotonergic and opioidergic neurotransmission in murine models. Fitoterapia, 2023 (PMID 37423501).
  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Tabercarpamines A-J, apoptosis-inducing indole alkaloids from the leaves of Tabernaemontana corymbosa. J Nat Prod, 2014 (PMID 24773071).

Compound-Protein Relationships


Compound Activities

    • Antibacterial
    • Antimycobacterial
    • Antidepressant
    • Antitumor
    • Antiinflammatory
    • Spasmolytic
    • Antiaddictive
    • Antileishmanial
    • Antinociceptive
    • Antioxidant
    • Ambulatory
    • Acetylcholinesterase inhibitory
    • Acetylbutyrylcholinesterase inhibitory
    • Cytotoxicity
    • Growth inhibitory
    • 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) -4.63
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.96
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.66
    Distribution Blood-Brain Barrier (Central Nervous System) -3.04
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.67
    Plasma Protein Binding 71.3
    Steady State Volume of Distribution 2.72
    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 Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.69
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.34
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.43
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.2
    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 -0.28
    Rat (Acute) 3.28
    Rat (Chronic Oral) 1.86
    Fathead Minnow 4.05
    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 388.1
    Hydration Free Energy -4.55
    Log(D) at pH=7.4 3.05
    Log(P) 3.57
    Log S -3.22
    Log(Vapor Pressure) -7.37
    Melting Point 186.89
    pKa Acid 12.96
    pKa Basic 8.36