Taberine A






Names

    • Taberine A

Attributes

  • Canonical SMILES

    C/C=C1[C@@]2([H])C[C@H](C3=C(OC)C=CC4=C3N[C@@]5(OC)[C@@]46CC[N@@]([C@@H]7O6)[C@@H]8[C@@]5(C(OC)=O)C[C@@]7([H])C[C@@H]8CC)C9=C(C[C@]([C@@]2(CO)C(OC)=O)([H])N(C)C\1)C%10=C(N9)C=CC=C%10

  • InChI

    InChI=1S/C45H56N4O8/c1-8-24-18-26-21-43(41(52)55-6)38(24)49-17-16-44(57-39(26)49)30-14-15-33(53-4)35(37(30)47-45(43,44)56-7)29-19-31-25(9-2)22-48(3)34(42(31,23-50)40(51)54-5)20-28-27-12-10-11-13-32(27)46-36(28)29/h9-15,24,26,29,31,34,38-39,46-47,50H,8,16-23H2,1-7H3/b25-9-/t24-,26+,29+,31+,34-,38-,39+,42-,43+,44+,45-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 134.82
  • #RotBonds: 7
  • MW: 780.9630000000001
  • HBD: 3
  • HBA: 11
  • logP: 5.286100000000005
  • Chemical Formula: C45H56N4O8


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) -5.73
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 258.65
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 34593.97
    Distribution Blood-Brain Barrier (Central Nervous System) -3.14
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.99
    Plasma Protein Binding 85.09
    Steady State Volume of Distribution 4.06
    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 Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 6.29
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -805.61
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.2
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 3.92
    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 Toxic
    T. Pyriformis -62783676.42
    Rat (Acute) 2.87
    Rat (Chronic Oral) 2.71
    Fathead Minnow 79251.95
    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 7057726.96
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.73
    Log(P) 4.65
    Log S -5.3
    Log(Vapor Pressure) -232310.09
    Melting Point 262.63
    pKa Acid -1640.96
    pKa Basic 8.78