5-Fluoro-voachalotine






Names

    • 5-Fluoro-voachalotine

Attributes

  • Canonical SMILES

    C\C=C(C4)/[C@@H]5CC(N4[C@@H]([C@@](CO)5C(OC)=O)C3)C2=C3C1=C(N2C)C=CC(F)=C1

  • InChI

    InChI=1S/C22H25FN2O3/c1-4-12-10-25-18-9-16(12)22(11-26,21(27)28-3)19(25)8-15-14-7-13(23)5-6-17(14)24(2)20(15)18/h4-7,16,18-19,26H,8-11H2,1-3H3/b12-4-/t16-,18?,19+,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.7
  • #RotBonds: 2
  • MW: 384.4510000000001
  • HBD: 1
  • HBA: 5
  • logP: 2.7167000000000012
  • Chemical Formula: C22H25FN2O3


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) -4.84
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.84
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.03
    Distribution Blood-Brain Barrier (Central Nervous System) -2.78
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.87
    Plasma Protein Binding 54.47
    Steady State Volume of Distribution 5.45
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.54
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -0.2
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.87
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.6
    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 -17.69
    Rat (Acute) 3.25
    Rat (Chronic Oral) 1.78
    Fathead Minnow 4.74
    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 472.23
    Hydration Free Energy -5.88
    Log(D) at pH=7.4 2.66
    Log(P) 2.73
    Log S -3.07
    Log(Vapor Pressure) -8.75
    Melting Point 198.32
    pKa Acid 7.65
    pKa Basic 7.34