Tabernaemontanine






Names

    • Tabernaemontanin
    • (-)-Tabernemontanine
    • MLS000737276
    • Tabernamontanine
    • Tabernaemontanine
    • NCI60_000192
    • Tabernemontanine
    • 20-Epidregamine
    • NSC-108088
    • 2134-98-7
    • Vobasan-17-oic acid,20-dihydro-3-oxo-, methyl ester, (20.beta.)-
    • CHEMBL1967575
    • NSC108088

Attributes

  • Canonical SMILES

    CC[C@@H]1CN([C@H]2CC3=C(C(=O)C[C@@H]1[C@@H]2C(=O)OC)NC4=CC=CC=C34)C

  • InChI

    InChI=1S/C21H26N2O3/c1-4-12-11-23(2)17-9-15-13-7-5-6-8-16(13)22-20(15)18(24)10-14(12)19(17)21(25)26-3/h5-8,12,14,17,19,22H,4,9-11H2,1-3H3/t12-,14+,17+,19+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.4
  • #RotBonds: 2
  • MW: 354.45000000000005
  • HBD: 1
  • HBA: 4
  • logP: 3.0424000000000015
  • Chemical Formula: C21H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM
    T. officinalis China - Cai20120227

External Databases


References

  • Accumulation of indole alkaloids in a suspension culture of Tabernaemontana divaricata. Planta Med, 1988 (PMID 17265301).
  • Alkylated monoterpene indole alkaloid derivatives as potent P-glycoprotein inhibitors in resistant cancer cells. Eur J Med Chem, 2021 (PMID 33189435).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine. J Nat Prod, 2014 (PMID 25333996).
  • Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans. Bioorg Med Chem Lett, 2009 (PMID 19525111).
  • Monoterpene bisindole alkaloids, from the African medicinal plant Tabernaemontana elegans, induce apoptosis in HCT116 human colon carcinoma cells. J Ethnopharmacol, 2013 (PMID 23872252).
  • Monoterpene indole alkaloid azine derivatives as MDR reversal agents. Bioorg Med Chem, 2018 (PMID 29233614).
  • Monoterpene indole alkaloid hydrazone derivatives with apoptosis inducing activity in human HCT116 colon and HepG2 liver carcinoma cells. Bioorg Med Chem Lett, 2015 (PMID 26169128).
  • Two new monoterpenoid indole alkaloids from Tabernaemontana divaricata. Nat Prod Res, 2019 (PMID 30445827).
  • Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata. Molecules, 2023 (PMID 37764440).
  • Vobatensines A-F, Cytotoxic Iboga-Vobasine Bisindoles from Tabernaemontana corymbosa. J Nat Prod, 2016 (PMID 26918761).

Compound-Protein Relationships


Compound Activities

    • Anticancer
    • BCRP efflux
    • Inhibition of MRP1
    • Collateral sensitivity
    • Caspase-3/7
    • Inhibitory
    • Apoptosis
    • Cytotoxicity
    • P-gp
    • Growth inhibitory

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) -4.76
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.95
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.59
    Distribution Blood-Brain Barrier (Central Nervous System) -2.3
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.94
    Plasma Protein Binding 65.37
    Steady State Volume of Distribution 4.39
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate 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 Non-Inhibitor
    Excretion Clearance 16.98
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.83
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.83
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.56
    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 -3.95
    Rat (Acute) 2.74
    Rat (Chronic Oral) 1.9
    Fathead Minnow 3.74
    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 425.8
    Hydration Free Energy -6.86
    Log(D) at pH=7.4 2.98
    Log(P) 3.02
    Log S -3.58
    Log(Vapor Pressure) -9.36
    Melting Point 213.02
    pKa Acid 7.44
    pKa Basic 5.65