Tabernamidine A






Names

    • Tabernamidine A

Attributes

  • Canonical SMILES

    O=C(OC)C1C2N(C)C/C(C1CC(C3=CC(NC5=C4CCN7[C@@H]6C5CC(C7)CC6C(C)=O)=C4C=C3)C8=C(C(C=CC=C9)=C9N8)C2)=C\C

  • InChI

    InChI=1S/C40H46N4O3/c1-5-23-20-43(3)35-18-31-25-8-6-7-9-33(25)41-38(31)30(17-29(23)36(35)40(46)47-4)24-10-11-26-27-12-13-44-19-22-14-28(21(2)45)39(44)32(15-22)37(27)42-34(26)16-24/h5-11,16,22,28-30,32,35-36,39,41-42H,12-15,17-20H2,1-4H3/b23-5+/t22?,28?,29?,30?,32?,35?,36?,39-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 81.43
  • #RotBonds: 3
  • MW: 630.8330000000003
  • HBD: 2
  • HBA: 5
  • logP: 6.332100000000007
  • Chemical Formula: C40H46N4O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution. J Nat Prod, 2016 (PMID 27077800).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Growth inhibitory

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) -5.92
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -3.33
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 301.9
    Distribution Blood-Brain Barrier (Central Nervous System) -3.43
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.67
    Plasma Protein Binding 63.98
    Steady State Volume of Distribution 4.73
    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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.6
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -2.33
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.08
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.98
    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 -546127.95
    Rat (Acute) 2.93
    Rat (Chronic Oral) 2.09
    Fathead Minnow 694.6
    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 57766.78
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.59
    Log(P) 4.67
    Log S -5.35
    Log(Vapor Pressure) -1889.81
    Melting Point 292.13
    pKa Acid 5.18
    pKa Basic 6.33