Tabernine A






Names

    • 6,8-dimethyl-5,7,17-triazatetracyclo[8.7.0.02,7.011,16]heptadeca-1,8,10,12,14,16-hexaene
    • 6,8-dimethyl-5,7,17-triazatetracyclo(8.7.0.02,7.011,16)heptadeca-1,8,10,12,14,16-hexaene
    • 1161940-61-9
    • CHEMBL555046
    • Tabernine A

Attributes

  • Canonical SMILES

    CC1=CC2=C(C3=C1C(C)NCC3)CC4=C2C=CC=C4

  • InChI

    InChI=1S/C18H19N/c1-11-9-16-14-6-4-3-5-13(14)10-17(16)15-7-8-19-12(2)18(11)15/h3-6,9,12,19H,7-8,10H2,1-2H3

  • Molecule Class: Alkaloids
  • TPSA: 12.03
  • #RotBonds: 0
  • MW: 249.35699999999997
  • HBD: 1
  • HBA: 1
  • logP: 3.7729200000000027
  • Chemical Formula: C18H19N


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM

External Databases


References

  • Tabernines A-C, beta-carbolines from the leaves of Tabernaemontana elegans. J Nat Prod, 2009 (PMID 19473031).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiproliferative

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) -4.86
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.79
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.74
    Distribution Blood-Brain Barrier (Central Nervous System) -2.24
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.08
    Plasma Protein Binding 35.33
    Steady State Volume of Distribution 2.55
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 6.37
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 2.52
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.03
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.58
    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 3.52
    Rat (Acute) 2.73
    Rat (Chronic Oral) 1.68
    Fathead Minnow 4.61
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 358.84
    Hydration Free Energy -6.77
    Log(D) at pH=7.4 3.5
    Log(P) 4.16
    Log S -3.53
    Log(Vapor Pressure) -6.18
    Melting Point 130.01
    pKa Acid 14.1
    pKa Basic 8.86