Tabernaricatine B






Names

    • Tabernaricatine B

Attributes

  • Canonical SMILES

    C(OC)(=O)[C@]12C3=C(C=4C(N3)=C(C(OC)=CC4)[C@@H]5C6=C(C=7C(N6)=CC=CC7)CC8([C@@]9(C(OC)=O)[C@@](C5)([C@H](CC)[C@@](N8C)(OC9)[H])[H])[H])CC[N@@]%10[C@]1([C@@H](CC)C[C@](C2)(C%10)[H])[H]

  • InChI

    InChI=1S/C44H54N4O6/c1-7-24-17-23-20-43(41(49)52-5)38-28(15-16-48(21-23)39(24)43)27-13-14-33(51-4)35(37(27)46-38)30-18-31-25(8-2)40-47(3)34(44(31,22-54-40)42(50)53-6)19-29-26-11-9-10-12-32(26)45-36(29)30/h9-14,23-25,30-31,34,39-40,45-46H,7-8,15-22H2,1-6H3/t23-,24+,25+,30-,31+,34?,39+,40+,43-,44+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 109.12000000000002
  • #RotBonds: 6
  • MW: 734.9379999999998
  • HBD: 2
  • HBA: 8
  • logP: 6.295300000000006
  • Chemical Formula: C44H54N4O6


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).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -5.71
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 74.84
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 10535.47
    Distribution Blood-Brain Barrier (Central Nervous System) -2.58
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.18
    Plasma Protein Binding 83.5
    Steady State Volume of Distribution 4.44
    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 9.49
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -249.62
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.31
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 5.66
    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 -19118630.2
    Rat (Acute) 2.92
    Rat (Chronic Oral) 1.48
    Fathead Minnow 24133.75
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Safe
    General Properties Boiling Point 2146692.98
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.98
    Log(P) 5.34
    Log S -5.69
    Log(Vapor Pressure) -70608.7
    Melting Point 299.33
    pKa Acid -465.08
    pKa Basic 7.0