Tabercorine B






Names

    • Tabercorine B

Attributes

  • Canonical SMILES

    C/C=C1[C@@]2([H])C[C@@H](C3=C(OC)C=CC4=C3N=C5[C@@]4(O)CCN(C6)[C@]7([H])[C@@]5(C(OC)=O)C[C@]6([H])C[C@]7([H])CC)C8=C(C[C@]([C@]2(C(OC)=O)COC9)([H])N9C\1)C%10=C(N8)C=CC=C%10

  • InChI

    InChI=1S/C44H52N4O7/c1-6-25-16-24-19-42(40(49)53-4)38(25)47(20-24)15-14-44(51)30-12-13-33(52-3)35(37(30)46-39(42)44)29-17-31-26(7-2)21-48-23-55-22-43(31,41(50)54-5)34(48)18-28-27-10-8-9-11-32(27)45-36(28)29/h7-13,24-25,29,31,34,38,45,51H,6,14-23H2,1-5H3/b26-7-/t24-,25-,29-,31+,34-,38-,42-,43-,44+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 125.92000000000002
  • #RotBonds: 5
  • MW: 748.9210000000002
  • HBD: 2
  • HBA: 10
  • logP: 5.605600000000006
  • Chemical Formula: C44H52N4O7


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).
  • New vobasinyl-ibogan type bisindole alkaloids from Tabernaemontana corymbosa. Fitoterapia, 2015 (PMID 25449423).
  • Taburnaemines A-I, Cytotoxic Vobasinyl-Iboga-Type Bisindole Alkaloids from Tabernaemontana corymbosa. J Nat Prod, 2018 (PMID 29319316).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Lysosomal acidification
    • Antiproliferative
    • Inhibitory
    • 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) -5.67
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 108.12
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 14872.02
    Distribution Blood-Brain Barrier (Central Nervous System) -2.42
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.14
    Plasma Protein Binding 81.54
    Steady State Volume of Distribution 3.65
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 5.87
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -348.75
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.91
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.99
    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 -26990921.72
    Rat (Acute) 2.99
    Rat (Chronic Oral) 1.64
    Fathead Minnow 34073.86
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Safe
    General Properties Boiling Point 3031902.11
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.29
    Log(P) 4.76
    Log S -5.15
    Log(Vapor Pressure) -99753.6
    Melting Point 257.57
    pKa Acid -673.66
    pKa Basic 7.46