11-Methoxyibogamine






Names

    • 11-Methoxyibogamine
    • CHEMBL468036
    • 11-methoxyibogamine

Attributes

  • Canonical SMILES

    CC[C@@H]4[C@H](N(C5)CC3)[C@@H](C[C@@H]5C4)C2=C3C1=CC=C(OC)C=C1N2

  • 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-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 28.259999999999998
  • #RotBonds: 2
  • MW: 310.441
  • HBD: 1
  • HBA: 2
  • logP: 3.936600000000003
  • Chemical Formula: C20H26N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. calcarea Madagascar 761054 -

External Databases


References

  • New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest. J Nat Prod, 2003 (PMID 12713407).

Compound-Protein Relationships

  • No relationship found

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) -4.72
    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 -1.55
    Distribution Blood-Brain Barrier (Central Nervous System) -3.14
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.51
    Plasma Protein Binding 63.73
    Steady State Volume of Distribution 2.59
    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 9.2
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.33
    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 7.38
    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 -2.14
    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 409.97
    Hydration Free Energy -4.54
    Log(D) at pH=7.4 3.31
    Log(P) 3.69
    Log S -3.17
    Log(Vapor Pressure) -7.62
    Melting Point 200.76
    pKa Acid 12.93
    pKa Basic 8.62