Tacamonidine






Names

    • Tacamonidine
    • CHEMBL3581900

Attributes

  • Canonical SMILES

    CC[C@@]1(C[C@@H]2CC(=O)N3C4=CC=CC=C4C5=C3[C@@H]2N(C1)CC5)O

  • InChI

    InChI=1S/C19H22N2O2/c1-2-19(23)10-12-9-16(22)21-15-6-4-3-5-13(15)14-7-8-20(11-19)17(12)18(14)21/h3-6,12,17,23H,2,7-11H2,1H3/t12-,17+,19-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 45.47
  • #RotBonds: 1
  • MW: 310.3970000000001
  • HBD: 1
  • HBA: 4
  • logP: 2.7454000000000014
  • Chemical Formula: C19H22N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Ibogan, tacaman, and cytotoxic bisindole alkaloids from tabernaemontana. Cononusine, an iboga alkaloid with unusual incorporation of a pyrrolidone moiety. J Nat Prod, 2015 (PMID 25919190).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Growth 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 -4.66
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.58
    Distribution Blood-Brain Barrier (Central Nervous System) -2.73
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.58
    Plasma Protein Binding 53.08
    Steady State Volume of Distribution 3.03
    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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 4.15
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.38
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.65
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 8.1
    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 -2.66
    Rat (Acute) 3.21
    Rat (Chronic Oral) 1.45
    Fathead Minnow 4.07
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 400.82
    Hydration Free Energy -6.5
    Log(D) at pH=7.4 1.16
    Log(P) 2.56
    Log S -2.06
    Log(Vapor Pressure) -7.84
    Melting Point 200.56
    pKa Acid 8.37
    pKa Basic 6.36