Tabernaricatine E






Names

    • Tabernaricatine E

Attributes

  • Canonical SMILES

    OC[C@]1(C(OC)=O)[C@@](CC2=C([C@](C3=C(OC)C=C4C(C(CCN(C5CC(C)=O)[C@]6([H])[C@@]7(C(OC)=O)C[C@]5([H])C[C@]6([H])CC)=C7N4)=C3)([H])C[C@]/81[H])NC9=C2C=CC=C9)([H])N(C)CC8=C\C

  • InChI

    InChI=1S/C47H58N4O7/c1-8-26-17-28-22-46(44(54)57-6)42-30(14-15-51(43(26)46)38(28)16-25(3)53)31-18-32(39(56-5)21-37(31)49-42)33-19-35-27(9-2)23-50(4)40(47(35,24-52)45(55)58-7)20-34-29-12-10-11-13-36(29)48-41(33)34/h9-13,18,21,26,28,33,35,38,40,43,48-49,52H,8,14-17,19-20,22-24H2,1-7H3/b27-9-/t26-,28-,33+,35+,38?,40-,43-,46+,47+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 137.19
  • #RotBonds: 8
  • MW: 791.002
  • HBD: 3
  • HBA: 9
  • logP: 6.199100000000007
  • Chemical Formula: C47H58N4O7


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).
  • 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

    • Antiproliferative
    • 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) -5.95
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 304.53
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 40589.01
    Distribution Blood-Brain Barrier (Central Nervous System) -3.6
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.13
    Plasma Protein Binding 90.47
    Steady State Volume of Distribution 3.65
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 10.31
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -946.2
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.09
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.14
    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 -73664434.66
    Rat (Acute) 2.88
    Rat (Chronic Oral) 2.23
    Fathead Minnow 92988.08
    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 8281159.77
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.86
    Log(P) 5.07
    Log S -5.39
    Log(Vapor Pressure) -272617.19
    Melting Point 286.62
    pKa Acid -1928.32
    pKa Basic 8.32