Tabernaesine J






Names

    • Tabernaesine J
    • CHEMBL4778257

Attributes

  • Canonical SMILES

    CC[C@@]12[C@H](O3)[C@H]3CN4[C@@H]1[C@@]5(CC4)C6=CC=CC=C6N(C[C@]7(C8)CN9CC[C@@]%10%11[C@@H]9[C@@]%12([C@H]7OCC%12)CC(C(OC)=O)=C%10NC%13=CC=CC=C%13%11)[C@@]5([H])[C@@]8([H])C2

  • InChI

    InChI=1S/C42H48N4O4/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)21-30-33(39)50-30)22-45-16-12-41-26-8-4-6-10-28(26)43-31(41)25(34(47)48-2)20-40(36(41)45)14-17-49-37(38)40/h4-11,24,30,32-33,35-37,43H,3,12-23H2,1-2H3/t24-,30-,32+,33-,35+,36+,37+,38+,39-,40+,41+,42+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 69.81
  • #RotBonds: 2
  • MW: 672.8700000000003
  • HBD: 1
  • HBA: 8
  • logP: 4.832200000000004
  • Chemical Formula: C42H48N4O4


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) -5.54
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 16.96
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 2921.53
    Distribution Blood-Brain Barrier (Central Nervous System) -2.8
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.24
    Plasma Protein Binding 68.01
    Steady State Volume of Distribution 2.98
    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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 5.82
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -72.84
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.33
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.61
    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 -5305363.88
    Rat (Acute) 3.66
    Rat (Chronic Oral) 1.72
    Fathead Minnow 6696.99
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 594421.0
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.05
    Log(P) 4.33
    Log S -4.86
    Log(Vapor Pressure) -19462.5
    Melting Point 289.29
    pKa Acid -102.97
    pKa Basic 8.19