3α-Hydroxymethyl-ibogamine






Names

    • 3α-Hydroxymethyl-ibogamine

Attributes

  • Canonical SMILES

    [H][C@]1(CO)N(CC2)[C@]3([H])[C@](C[C@]1([H])C[C@]3([H])CC)([H])C4=C2C5=C(N4)C=CC=C5

  • InChI

    InChI=1S/C20H26N2O/c1-2-12-9-13-10-16-19-15(14-5-3-4-6-17(14)21-19)7-8-22(20(12)16)18(13)11-23/h3-6,12-13,16,18,20-21,23H,2,7-11H2,1H3/t12-,13-,16-,18+,20-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 39.26
  • #RotBonds: 2
  • MW: 310.441
  • HBD: 2
  • HBA: 2
  • logP: 3.2889000000000017
  • Chemical Formula: C20H26N2O


Species

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

External Databases


References

  • Three New Indole Alkaloids from Tabernaemontana divaricata. Nat Prod Bioprospect, 2018 (PMID 29754315).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cidal
    • 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) -4.82
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.08
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.22
    Distribution Blood-Brain Barrier (Central Nervous System) -3.09
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.59
    Plasma Protein Binding 73.78
    Steady State Volume of Distribution 2.54
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-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 7.89
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 0.58
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.54
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.78
    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 -2.25
    Rat (Acute) 2.96
    Rat (Chronic Oral) 1.85
    Fathead Minnow 4.04
    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 413.39
    Hydration Free Energy -4.71
    Log(D) at pH=7.4 2.92
    Log(P) 3.21
    Log S -3.13
    Log(Vapor Pressure) -8.92
    Melting Point 206.89
    pKa Acid 12.35
    pKa Basic 7.69