5-Fluoro-isovoacangine






Names

    • 5-Fluoro-isovoacangine

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C22H27FN2O3/c1-4-13-7-12-10-22(21(26)28-3)19-14(5-6-25(11-12)20(13)22)15-8-16(23)18(27-2)9-17(15)24-19/h8-9,12-13,20,24H,4-7,10-11H2,1-3H3/t12-,13+,20?,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.559999999999995
  • #RotBonds: 3
  • MW: 386.4670000000001
  • HBD: 1
  • HBA: 4
  • logP: 3.4029000000000016
  • Chemical Formula: C22H27FN2O3


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) -4.63
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.94
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.23
    Distribution Blood-Brain Barrier (Central Nervous System) -2.89
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.89
    Plasma Protein Binding 55.88
    Steady State Volume of Distribution 4.89
    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 Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.99
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.78
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.13
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.4
    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 -20.66
    Rat (Acute) 2.93
    Rat (Chronic Oral) 1.97
    Fathead Minnow 4.12
    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 452.94
    Hydration Free Energy -5.68
    Log(D) at pH=7.4 3.38
    Log(P) 3.06
    Log S -3.97
    Log(Vapor Pressure) -8.21
    Melting Point 223.74
    pKa Acid 8.74
    pKa Basic 6.94