Tabernaricatine C






Names

    • Tabernaricatine C

Attributes

  • Canonical SMILES

    C/C=C1[C@@]2([H])C[C@@](C3=C(OC)C=C4C(C(CCN(C5)[C@]6([H])[C@@]7(C(OC)=O)C[C@]5([H])C[C@]6([H])CC)=C7[N]4)=C3)([H])C8=C(C[C@]([C@@]2(C(OC)=O)COC9)([H])[N@]9C\1)C%10=C(N8)C=CC=C%10

  • InChI

    InChI=1S/C44H51N4O6/c1-6-25-14-24-19-43(41(49)52-4)39-28(12-13-47(20-24)40(25)43)29-15-30(36(51-3)18-35(29)46-39)31-16-33-26(7-2)21-48-23-54-22-44(33,42(50)53-5)37(48)17-32-27-10-8-9-11-34(27)45-38(31)32/h7-11,15,18,24-25,31,33,37,40,45H,6,12-14,16-17,19-23H2,1-5H3/b26-7-/t24-,25-,31+,33+,37-,40-,43+,44+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 107.43
  • #RotBonds: 5
  • MW: 731.9140000000001
  • HBD: 1
  • HBA: 8
  • logP: 6.2925000000000075
  • Chemical Formula: C44H51N4O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).
  • Cytotoxic Monoterpenoid Indole Alkaloids from Tabernaemontana corymbosa as Potent Autophagy Inhibitors by the Attenuation of Lysosomal Acidification. J Nat Prod, 2020 (PMID 32356659).
  • 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
    • Cytotoxicity

Predicted NMR Spectral Data

  • No NMR data available.

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) -5.85
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 76.25
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 10682.33
    Distribution Blood-Brain Barrier (Central Nervous System) -2.89
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.31
    Plasma Protein Binding 81.27
    Steady State Volume of Distribution 5.25
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate 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 7.56
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -252.94
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.37
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.73
    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 -19388308.33
    Rat (Acute) 3.31
    Rat (Chronic Oral) 1.29
    Fathead Minnow 24477.07
    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 2177216.02
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.54
    Log(P) 4.54
    Log S -5.13
    Log(Vapor Pressure) -71610.47
    Melting Point 240.81
    pKa Acid -468.62
    pKa Basic 7.46