5-Fluoro-catharanthine






Names

    • 5-Fluoro-catharanthine

Attributes

  • Canonical SMILES

    CCC4C(N(C5)CC3)[C@](C[C@@H]5C4)([C@](OC)=O)C1=C3C(C=C(F)C=C2)=C2N1

  • InChI

    InChI=1S/C21H25FN2O2/c1-3-13-8-12-10-21(20(25)26-2)18-15(6-7-24(11-12)19(13)21)16-9-14(22)4-5-17(16)23-18/h4-5,9,12-13,19,23H,3,6-8,10-11H2,1-2H3/t12-,13?,19?,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 45.33
  • #RotBonds: 2
  • MW: 356.44100000000003
  • HBD: 1
  • HBA: 3
  • logP: 3.394300000000001
  • Chemical Formula: C21H25FN2O2


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) -4.8
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.95
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.1
    Distribution Blood-Brain Barrier (Central Nervous System) -2.55
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.9
    Plasma Protein Binding 56.05
    Steady State Volume of Distribution 5.16
    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 10.21
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.83
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.79
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.87
    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 -5.54
    Rat (Acute) 3.04
    Rat (Chronic Oral) 2.0
    Fathead Minnow 4.16
    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 431.3
    Hydration Free Energy -4.16
    Log(D) at pH=7.4 3.49
    Log(P) 3.37
    Log S -4.01
    Log(Vapor Pressure) -8.25
    Melting Point 226.16
    pKa Acid 9.36
    pKa Basic 7.44