5-Fluoro-12-methoxy-Nb-methyl-voachalotine






Names

    • 5-Fluoro-12-methoxy-Nb-methyl-voachalotine

Attributes

  • Canonical SMILES

    C/C=C2C[N+]1(C)[C@@H]3CC4=C(N(C)C5=C(OC)C=C(F)C=C45)C1C[C@H]\2C(C(OC)=O)3CO

  • InChI

    InChI=1S/C24H30FN2O4/c1-6-13-11-27(3)18-10-17(13)24(12-28,23(29)31-5)20(27)9-16-15-7-14(25)8-19(30-4)22(15)26(2)21(16)18/h6-8,17-18,20,28H,9-12H2,1-5H3/q+1/b13-6+/t17-,18?,20-,24?,27?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 60.69
  • #RotBonds: 3
  • MW: 429.5120000000002
  • HBD: 1
  • HBA: 5
  • logP: 2.8699000000000017
  • Chemical Formula: C24H30FN2O4+


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) -5.3
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.76
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.0
    Distribution Blood-Brain Barrier (Central Nervous System) -3.64
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.91
    Plasma Protein Binding 52.3
    Steady State Volume of Distribution 2.5
    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 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 6.2
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 0.95
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.26
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.43
    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 -64.36
    Rat (Acute) 3.04
    Rat (Chronic Oral) 1.81
    Fathead Minnow 4.8
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 501.17
    Hydration Free Energy -3.62
    Log(D) at pH=7.4 2.16
    Log(P) 0.05
    Log S -1.87
    Log(Vapor Pressure) -9.96
    Melting Point 223.9
    pKa Acid 6.87
    pKa Basic 5.54