Tabernaricatine A






Names

    • Tabernaricatine A

Attributes

  • Canonical SMILES

    C[C@H](O1)[C@]21[C@@]3([H])C[C@@](C4=C5C(C(CCN(C6)[C@]7([H])[C@@]8(C(OC)=O)C[C@]6([H])C[C@]7([H])CC)=C8[N]5)=CC=C4OC)([H])C9=C(C[C@]%10([H])N(C)[C@@]2([H])OC[C@]%103C(OC)=O)C%11=C(N9)C=CC=C%11

  • InChI

    InChI=1S/C44H51N4O7/c1-7-24-16-23-19-42(40(49)52-5)37-27(14-15-48(20-23)38(24)42)26-12-13-31(51-4)34(36(26)46-37)29-17-32-43(41(50)53-6)21-54-39(44(32)22(2)55-44)47(3)33(43)18-28-25-10-8-9-11-30(25)45-35(28)29/h8-13,22-24,29,32-33,38-39,45H,7,14-21H2,1-6H3/t22-,23-,24-,29+,32-,33-,38-,39-,42+,43+,44-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 119.96000000000001
  • #RotBonds: 5
  • MW: 747.9130000000001
  • HBD: 1
  • HBA: 9
  • logP: 5.502100000000005
  • Chemical Formula: C44H51N4O7


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).
  • New vobasinyl-ibogan type bisindole alkaloids from Tabernaemontana corymbosa. Fitoterapia, 2015 (PMID 25449423).
  • Tabercorymines A and B, Two Vobasinyl-Ibogan-Type Bisindole Alkaloids from Tabernaemontana corymbosa. Org Lett, 2017 (PMID 28876071).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiproliferative
    • Inhibitory
    • 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) -5.54
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 125.55
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 17134.17
    Distribution Blood-Brain Barrier (Central Nervous System) -2.51
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.1
    Plasma Protein Binding 65.57
    Steady State Volume of Distribution 3.88
    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 Non-Inhibitor
    Excretion Clearance 6.46
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -401.53
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.26
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 5.83
    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 -31098115.47
    Rat (Acute) 3.6
    Rat (Chronic Oral) 0.92
    Fathead Minnow 39257.68
    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 3494104.33
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.31
    Log(P) 3.95
    Log S -5.13
    Log(Vapor Pressure) -114978.58
    Melting Point 234.77
    pKa Acid -791.2
    pKa Basic 7.86