Tabernaesine E






Names

    • Tabernaesine E
    • CHEMBL4745532

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%11CCO[C@H]%10CCN%12CC[C@](C%13=CC=C(C(O)=C%133)CN(CC)CC)2[C@H]%11%12

  • InChI

    InChI=1S/C47H59N5O6/c1-4-49(5-2)25-28-10-11-32-35(36(28)53)52-27-42(22-29-23-43-15-20-57-34(43)12-17-50-19-14-46(32,40(43)50)47(29,52)55)26-51-18-13-45-31-8-6-7-9-33(31)48-37(45)30(38(54)56-3)24-44(39(45)51)16-21-58-41(42)44/h6-11,29,34,39-41,48,53,55H,4-5,12-27H2,1-3H3/t29-,34+,39+,40+,41+,42+,43-,44+,45+,46-,47-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 110.21000000000001
  • #RotBonds: 5
  • MW: 790.0179999999998
  • HBD: 3
  • HBA: 11
  • logP: 4.7012000000000045
  • Chemical Formula: C47H59N5O6


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) -5.77
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 1082.48
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 142259.49
    Distribution Blood-Brain Barrier (Central Nervous System) -3.07
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.14
    Plasma Protein Binding 86.86
    Steady State Volume of Distribution 4.09
    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 3.55
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -3311.29
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.23
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.27
    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 -258192916.43
    Rat (Acute) 2.96
    Rat (Chronic Oral) 2.2
    Fathead Minnow 325913.38
    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 29036162.69
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 -1.61
    Log(P) 3.63
    Log S -4.79
    Log(Vapor Pressure) -956019.02
    Melting Point 315.71
    pKa Acid -6899.53
    pKa Basic -22.25