Taberisidine






Names

    • Taberisidine

Attributes

  • Canonical SMILES

    COC(=O)[C@H]1[C@@H](CC[C@H]([C@@H]1C(=O)C2=NC=CC3=C2NC4=CC=CC=C34)CO)O

  • InChI

    InChI=1S/C21H22N2O5/c1-28-21(27)17-15(25)7-6-11(10-24)16(17)20(26)19-18-13(8-9-22-19)12-4-2-3-5-14(12)23-18/h2-5,8-9,11,15-17,23-25H,6-7,10H2,1H3/t11-,15+,16-,17-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 112.51000000000002
  • #RotBonds: 4
  • MW: 382.4160000000001
  • HBD: 3
  • HBA: 6
  • logP: 2.0674
  • Chemical Formula: C21H22N2O5


Species

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

External Databases


References

  • A Hexacyclic, Iboga-Derived Monoterpenoid Indole with a Contracted Tetrahydroazepine C-Ring and Incorporation of an Isoxazolidine Moiety, a Seco-Corynanthean, an Aspidosperma-Aspidosperma Bisindole with Anticancer Properties, and the Absolute Configuration of the Pyridopyrimidine Indole Alkaloid, Vernavosine. J Nat Prod, 2016 (PMID 27759387).

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) -5.33
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.74
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.43
    Distribution Blood-Brain Barrier (Central Nervous System) -3.19
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.08
    Plasma Protein Binding 76.05
    Steady State Volume of Distribution 0.85
    Metabolism Breast Cancer Resistance Protein 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 Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 4.43
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Safe
    Bioconcentration Factor 0.21
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.05
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.2
    Micronucleos Toxic
    NR-AhR Toxic
    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 -17.85
    Rat (Acute) 2.93
    Rat (Chronic Oral) 2.61
    Fathead Minnow 4.09
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Safe
    General Properties Boiling Point 488.43
    Hydration Free Energy -7.98
    Log(D) at pH=7.4 2.68
    Log(P) 1.92
    Log S -3.99
    Log(Vapor Pressure) -9.87
    Melting Point 201.18
    pKa Acid 7.85
    pKa Basic 5.96