Tabernaesine C






Names

    • CHEMBL4760847
    • Tabernaesine C

Attributes

  • Canonical SMILES

    COC(C(C[C@]12[C@H]3OCC2)=C(NC4=CC=CC=C45)[C@]65[C@H]1N(CC6)C[C@@]3(C7)CN8[C@@]9(O)[C@@]7([H])C[C@@]%10(C%11)[C@H]%12[C@](CCN%12CC[C@@H]%10OC%11=O)9C%13=CC=CC(O)=C8%13)=O

  • InChI

    InChI=1S/C42H46N4O7/c1-51-33(49)24-19-38-12-16-52-36(38)37(21-45-14-10-40(34(38)45)25-5-2-3-7-27(25)43-32(24)40)17-23-18-39-20-30(48)53-29(39)9-13-44-15-11-41(35(39)44)26-6-4-8-28(47)31(26)46(22-37)42(23,41)50/h2-8,23,29,34-36,43,47,50H,9-22H2,1H3/t23-,29+,34+,35+,36+,37+,38+,39+,40+,41-,42-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 124.04000000000002
  • #RotBonds: 1
  • MW: 718.8510000000003
  • HBD: 3
  • HBA: 11
  • logP: 3.3860000000000023
  • Chemical Formula: C42H46N4O7


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) -5.62
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 88.61
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 12331.47
    Distribution Blood-Brain Barrier (Central Nervous System) -2.75
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.97
    Plasma Protein Binding 73.26
    Steady State Volume of Distribution 4.43
    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 4.08
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -291.59
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.24
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.94
    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 Safe
    T. Pyriformis -22382015.18
    Rat (Acute) 3.03
    Rat (Chronic Oral) 2.12
    Fathead Minnow 28253.34
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 2513776.03
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 3.94
    Log(P) 2.76
    Log S -4.49
    Log(Vapor Pressure) -82677.29
    Melting Point 374.56
    pKa Acid -549.98
    pKa Basic 7.38