Tabernaesine I






Names

    • Tabernaesine I
    • CHEMBL4764293

Attributes

  • Canonical SMILES

    O[C@H]1[C@]2(C[C@]3([H])[C@]4(O)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/C42H50N4O6/c1-3-38-19-24-18-37(23-46-29-11-7-5-9-27(29)41(42(24,46)50)13-16-44(35(38)41)21-30(47)32(38)48)22-45-15-12-40-26-8-4-6-10-28(26)43-31(40)25(33(49)51-2)20-39(34(40)45)14-17-52-36(37)39/h4-11,24,30,32,34-36,43,47-48,50H,3,12-23H2,1-2H3/t24-,30+,32-,34+,35+,36+,37-,38-,39+,40+,41-,42-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 117.97
  • #RotBonds: 2
  • MW: 706.8840000000002
  • HBD: 4
  • HBA: 10
  • logP: 3.106600000000003
  • Chemical Formula: C42H50N4O6


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) -5.85
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 41.51
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 6184.02
    Distribution Blood-Brain Barrier (Central Nervous System) -3.2
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.1
    Plasma Protein Binding 88.89
    Steady State Volume of Distribution 3.23
    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 Non-Inhibitor
    Excretion Clearance 3.05
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -150.14
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.32
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.83
    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 -11224424.41
    Rat (Acute) 3.17
    Rat (Chronic Oral) 2.73
    Fathead Minnow 14169.03
    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 1259426.69
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.32
    Log(P) 2.82
    Log S -4.62
    Log(Vapor Pressure) -41353.45
    Melting Point 309.96
    pKa Acid -250.55
    pKa Basic 7.63