5-Fluoro-19-(S)-hydroxy-ibogamine






Names

    • 5-Fluoro-19-(S)-hydroxy-ibogamine

Attributes

  • Canonical SMILES

    CC(O)[C@H]4C(N(C5)CC3)[C@@H](C[C@@H]5C4)C1=C3C(C=C(F)C=C2)=C2N1

  • InChI

    InChI=1S/C19H23FN2O/c1-10(23)14-6-11-7-16-18-13(4-5-22(9-11)19(14)16)15-8-12(20)2-3-17(15)21-18/h2-3,8,10-11,14,16,19,21,23H,4-7,9H2,1H3/t10?,11-,14-,16-,19?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 39.26
  • #RotBonds: 1
  • MW: 314.404
  • HBD: 2
  • HBA: 2
  • logP: 3.0379000000000005
  • Chemical Formula: C19H23FN2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • Precursor-directed Biosynthesis in Tabernaemontana catharinensis as a New Avenue for Alzheimer's Disease-modifying Agents. Planta Med, 2021 (PMID 33321518).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Inhibitory

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) -4.88
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.05
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.31
    Distribution Blood-Brain Barrier (Central Nervous System) -3.0
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.41
    Plasma Protein Binding 53.51
    Steady State Volume of Distribution 4.41
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate 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 10.91
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.57
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.91
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.83
    Micronucleos Toxic
    NR-AhR Safe
    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 -3.16
    Rat (Acute) 3.29
    Rat (Chronic Oral) 1.75
    Fathead Minnow 4.11
    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 388.93
    Hydration Free Energy -6.01
    Log(D) at pH=7.4 2.19
    Log(P) 2.16
    Log S -2.83
    Log(Vapor Pressure) -7.91
    Melting Point 216.28
    pKa Acid 10.06
    pKa Basic 7.67