22-Deethyl fuchsiaefoline






Names

    • 22-Deethyl fuchsiaefoline

Attributes

  • Canonical SMILES

    COC1=CC=CC2=C1N(C)C3=C2C[C@@H]([C@@H]4C(O)=O)[N+](C/5)(C)[C@@]3([H])C[C@@H]4C5=C/C

  • InChI

    InChI=1S/C22H26N2O3/c1-5-12-11-24(3)16-10-15-13-7-6-8-18(27-4)21(13)23(2)20(15)17(24)9-14(12)19(16)22(25)26/h5-8,14,16-17,19H,9-11H2,1-4H3/p+1/b12-5-/t14-,16+,17+,19-,24?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 51.46
  • #RotBonds: 2
  • MW: 367.46900000000016
  • HBD: 1
  • HBA: 3
  • logP: 3.2799000000000023
  • Chemical Formula: C22H27N2O3+


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. macrocarpa Indonesia 761080 -

External Databases


References

  • Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack. J Nat Med, 2019 (PMID 31140017).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimalarial
    • Cytotoxicity

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) -5.27
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.82
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -0.92
    Distribution Blood-Brain Barrier (Central Nervous System) -3.6
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.69
    Plasma Protein Binding 64.22
    Steady State Volume of Distribution 0.95
    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 Non-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 1.77
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 0.23
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.12
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 3.36
    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 -8.07
    Rat (Acute) 3.04
    Rat (Chronic Oral) 1.64
    Fathead Minnow 4.31
    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 485.54
    Hydration Free Energy -3.82
    Log(D) at pH=7.4 -0.13
    Log(P) 0.07
    Log S -1.5
    Log(Vapor Pressure) -10.94
    Melting Point 279.72
    pKa Acid 3.3
    pKa Basic 6.84