Tabernanthine






Names

    • (1R,15R,17S,18S)-17-ethyl-6-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene
    • IBOGAMINE, 13-METHOXY-
    • Tabernanthine
    • (1R,15R,17S,18S)-17-ethyl-6-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene
    • AKOS040762389
    • 13-Methoxyibogamine
    • 83-94-3
    • UNII-TV52I1S16D
    • (1-methyl-1-((8S)-2-oxo-8,9-dihydrofuro(2,3-h)chromen-8-yl)ethyl) 3-methylbut-2-enoate
    • [1-methyl-1-[(8S)-2-oxo-8,9-dihydrofuro[2,3-h]chromen-8-yl]ethyl] 3-methylbut-2-enoate
    • TABERNANTHINE [MI]
    • TV52I1S16D
    • SCHEMBL3844372
    • DTXCID901016560
    • TABERNANTHIN
    • DTXSID50878514

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=CC(=C5)OC

  • InChI

    InChI=1S/C20H26N2O/c1-3-13-8-12-9-17-19-16(6-7-22(11-12)20(13)17)15-5-4-14(23-2)10-18(15)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3/t12-,13+,17+,20+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 28.26
  • #RotBonds: 2
  • MW: 310.44100000000003
  • HBD: 1
  • HBA: 2
  • logP: 3.936600000000003
  • Chemical Formula: C20H26N2O


Species

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

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).
  • New Iboga-Type Indole Alkaloids from Tabernaemontana divaricata. Nat Prod Bioprospect, 2019 (PMID 31724098).

Compound-Protein Relationships


Compound Activities

    • 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) -4.7
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.95
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.56
    Distribution Blood-Brain Barrier (Central Nervous System) -3.15
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.51
    Plasma Protein Binding 63.32
    Steady State Volume of Distribution 2.58
    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 9.31
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.3
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.09
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.37
    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 -2.02
    Rat (Acute) 3.0
    Rat (Chronic Oral) 1.69
    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 411.02
    Hydration Free Energy -4.52
    Log(D) at pH=7.4 3.27
    Log(P) 3.59
    Log S -3.17
    Log(Vapor Pressure) -7.6
    Melting Point 199.77
    pKa Acid 12.88
    pKa Basic 8.62