Tabernaelegantine C






Names

    • Tabernaelegantine C

Attributes

  • Canonical SMILES

    CC[C@@]1([H])C[C@]2([H])C[C@@]([C@@]1([H])[N@](C2)CC3)(C(OC)=O)C4=C3C5=CC=C(OC)C([C@@H]6C7=C(C[C@@H]([C@H]8C(OC)=O)N(C)C[C@H](CC)[C@H]8C6)C9=CC=CC=C9N7)=C5N4

  • InChI

    InChI=1S/C43H54N4O5/c1-7-24-17-23-20-43(42(49)52-6)39-28(15-16-47(21-23)40(24)43)27-13-14-34(50-4)36(38(27)45-39)31-18-29-25(8-2)22-46(3)33(35(29)41(48)51-5)19-30-26-11-9-10-12-32(26)44-37(30)31/h9-14,23-25,29,31,33,35,40,44-45H,7-8,15-22H2,1-6H3/t23-,24+,25+,29-,31-,33+,35+,40+,43-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 99.88999999999999
  • #RotBonds: 6
  • MW: 706.928
  • HBD: 2
  • HBA: 7
  • logP: 6.568800000000007
  • Chemical Formula: C43H54N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM

External Databases


References

  • Monoterpene bisindole alkaloids, from the African medicinal plant Tabernaemontana elegans, induce apoptosis in HCT116 human colon carcinoma cells. J Ethnopharmacol, 2013 (PMID 23872252).
  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticancer
    • Antiinflammatory
    • Acetylcholinesterase inhibitory
    • 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) -5.91
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 17.89
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 3099.61
    Distribution Blood-Brain Barrier (Central Nervous System) -3.27
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.31
    Plasma Protein Binding 89.95
    Steady State Volume of Distribution 4.76
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate 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 10.3
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -75.34
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.12
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 7.19
    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 -5623551.07
    Rat (Acute) 2.79
    Rat (Chronic Oral) 2.41
    Fathead Minnow 7100.17
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 628881.89
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 6.06
    Log(P) 5.73
    Log S -5.76
    Log(Vapor Pressure) -20640.88
    Melting Point 284.48
    pKa Acid -114.57
    pKa Basic 6.16