Tabernaesine A






Names

    • CHEMBL4751912
    • Tabernaesine A

Attributes

  • Canonical SMILES

    CC[C@]12C[C@]3([H])[C@]4([H])N(C5=CC=CC=C5[C@@]46CCN(C[C@@H]7[C@H]2O7)[C@H]61)C[C@]8(C3)C(N9CC[C@@]%10%11[C@@H]9[C@@]%12([C@H]8OCC%12)CC(C(OC)=O)=C%10NC%13=CC=CC=C%13%11)=O

  • InChI

    InChI=1S/C42H46N4O5/c1-3-38-18-23-19-40(22-46-28-11-7-5-9-26(28)42(31(23)46)12-15-44(34(38)42)21-29-32(38)51-29)36-39(14-17-50-36)20-24(33(47)49-2)30-41(13-16-45(35(39)41)37(40)48)25-8-4-6-10-27(25)43-30/h4-11,23,29,31-32,34-36,43H,3,12-22H2,1-2H3/t23-,29+,31-,32+,34-,35-,36+,38+,39-,40-,41-,42-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 86.88
  • #RotBonds: 2
  • MW: 686.8530000000004
  • HBD: 1
  • HBA: 8
  • logP: 4.358800000000003
  • Chemical Formula: C42H46N4O5


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) -5.53
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 29.72
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 4590.78
    Distribution Blood-Brain Barrier (Central Nervous System) -2.92
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.36
    Plasma Protein Binding 69.12
    Steady State Volume of Distribution 2.64
    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 5.36
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -113.92
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.84
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.97
    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 -8334560.61
    Rat (Acute) 3.24
    Rat (Chronic Oral) 1.88
    Fathead Minnow 10521.99
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 934729.23
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.72
    Log(P) 3.86
    Log S -5.41
    Log(Vapor Pressure) -30679.0
    Melting Point 346.41
    pKa Acid -181.96
    pKa Basic 6.8