Tabernaesine D






Names

    • CHEMBL4754512
    • Tabernaesine D

Attributes

  • Canonical SMILES

    O[C@]12N3C[C@]4([C@H]5[C@]6(CC(C(OC)=O)=C7NC8=CC=CC=C8[C@]79[C@H]6N(C4)CC9)CCO5)C[C@]1([H])C[C@]%10([C@H]%11[C@@]2(CCN%11CC[C@@H]%10O%12)C%13=CC=C(C(O)=C%133)CN(CC)CC)CC%12=O

  • InChI

    InChI=1S/C47H57N5O7/c1-4-49(5-2)24-27-10-11-31-35(36(27)54)52-26-42(20-28-21-44-23-34(53)59-33(44)12-16-50-18-14-46(31,40(44)50)47(28,52)56)25-51-17-13-45-30-8-6-7-9-32(30)48-37(45)29(38(55)57-3)22-43(39(45)51)15-19-58-41(42)43/h6-11,28,33,39-41,48,54,56H,4-5,12-26H2,1-3H3/t28-,33+,39+,40+,41+,42+,43+,44+,45+,46-,47-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 127.28
  • #RotBonds: 5
  • MW: 804.0009999999999
  • HBD: 3
  • HBA: 12
  • logP: 4.227800000000004
  • Chemical Formula: C47H57N5O7


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. pachysiphon Nigeria, Netherlands 403125 HXJ20171220

External Databases


References

  • Tabernaesines A-I, Cytotoxic Aspidosperma-Aspidosperma-Type Bisindole Alkaloids from Tabernaemontana pachysiphon. J Nat Prod, 2020 (PMID 33112136).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -5.79
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 1517.69
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 199144.28
    Distribution Blood-Brain Barrier (Central Nervous System) -3.0
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.05
    Plasma Protein Binding 83.83
    Steady State Volume of Distribution 3.69
    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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 2.97
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -4634.56
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.15
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.06
    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 -361436033.81
    Rat (Acute) 2.92
    Rat (Chronic Oral) 2.1
    Fathead Minnow 456236.03
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 40647672.48
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 -6.91
    Log(P) 3.04
    Log S -4.59
    Log(Vapor Pressure) -1338387.94
    Melting Point 326.71
    pKa Acid -9685.62
    pKa Basic -45.2