Tabernaesine F






Names

    • Tabernaesine F
    • CHEMBL4763032

Attributes

  • Canonical SMILES

    O[C@H]1[C@]2(C[C@]3([H])[C@]4([H])N(C5=CC=CC=C5[C@@]46CCN(C[C@@H]1O)[C@H]62)C[C@]7(C3)CN8CC[C@@]9%10[C@@H]8[C@@]%11([C@H]7OCC%11)CC(C(OC)=O)=C9NC%12=CC=CC=C%12%10)CC

  • InChI

    InChI=1S/C42H50N4O5/c1-3-39-19-24-18-38(23-46-29-11-7-5-9-27(29)42(32(24)46)13-15-44(35(39)42)21-30(47)33(39)48)22-45-16-12-41-26-8-4-6-10-28(26)43-31(41)25(34(49)50-2)20-40(36(41)45)14-17-51-37(38)40/h4-11,24,30,32-33,35-37,43,47-48H,3,12-23H2,1-2H3/t24-,30+,32+,33-,35+,36+,37+,38+,39-,40+,41+,42+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 97.74000000000001
  • #RotBonds: 2
  • MW: 690.8850000000002
  • HBD: 3
  • HBA: 9
  • logP: 3.7866000000000026
  • Chemical Formula: C42H50N4O5


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) -5.84
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 28.05
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 4397.3
    Distribution Blood-Brain Barrier (Central Nervous System) -2.92
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.21
    Plasma Protein Binding 89.91
    Steady State Volume of Distribution 3.75
    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 4.06
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -108.98
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.47
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.31
    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 -7982772.7
    Rat (Acute) 3.27
    Rat (Chronic Oral) 2.54
    Fathead Minnow 10077.04
    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 895153.33
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.62
    Log(P) 3.64
    Log S -4.61
    Log(Vapor Pressure) -29358.49
    Melting Point 317.03
    pKa Acid -166.41
    pKa Basic 8.12