Taberine I






Names

    • Taberine I

Attributes

  • Canonical SMILES

    [H][C@]1([C@@]2([H])[C@]3(CC(OC)=O)C4=C(C5=C(C=CC=C5)N4CN2CCC(C1)C3)C=O)[C@H](C)O

  • InChI

    InChI=1S/C23H28N2O4/c1-14(27)17-9-15-7-8-24-13-25-19-6-4-3-5-16(19)18(12-26)22(25)23(10-15,21(17)24)11-20(28)29-2/h3-6,12,14-15,17,21,27H,7-11,13H2,1-2H3/t14-,15?,17+,21-,23-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.77
  • #RotBonds: 4
  • MW: 396.4870000000002
  • HBD: 1
  • HBA: 6
  • logP: 2.707100000000001
  • Chemical Formula: C23H28N2O4


Species

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

External Databases


References

  • Cytotoxic Monoterpenoid Indole Alkaloids from Tabernaemontana corymbosa as Potent Autophagy Inhibitors by the Attenuation of Lysosomal Acidification. J Nat Prod, 2020 (PMID 32356659).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Lysosomal acidification
    • 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) -4.88
    Human Oral Bioavailability 20% 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 Substrate
    Skin Permeability -2.01
    Distribution Blood-Brain Barrier (Central Nervous System) -2.37
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.54
    Plasma Protein Binding 47.56
    Steady State Volume of Distribution 2.2
    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 Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.19
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.13
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.28
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 8.12
    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 -27.76
    Rat (Acute) 3.65
    Rat (Chronic Oral) 1.7
    Fathead Minnow 4.0
    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 481.14
    Hydration Free Energy -4.7
    Log(D) at pH=7.4 2.13
    Log(P) 1.29
    Log S -3.08
    Log(Vapor Pressure) -9.16
    Melting Point 178.19
    pKa Acid 7.47
    pKa Basic 6.46