Tabernaemontine






Names

    • Tabernaemontanin
    • (-)-Tabernemontanine
    • MLS000737276
    • Tabernamontanine
    • NCI60_000192
    • Tabernemontanine
    • Tabernaemontine
    • 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]1C2C(=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. penduliflora Cameroon, 37036/HNC, Nigeria 761088 40,411 HCN

External Databases


References

  • Antiplasmodial activities of indole alkaloids from Tabernaemontana penduliflora K. Schum (Apocynaceae). Fitoterapia, 2021 (PMID 34029654).
  • Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine. J Nat Prod, 2014 (PMID 25333996).
  • Two new monoterpenoid indole alkaloids from Tabernaemontana divaricata. Nat Prod Res, 2019 (PMID 30445827).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -4.78
    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 Non-Substrate
    Skin Permeability -1.62
    Distribution Blood-Brain Barrier (Central Nervous System) -2.29
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.94
    Plasma Protein Binding 58.04
    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 17.0
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.78
    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 6.58
    Micronucleos Toxic
    NR-AhR Toxic
    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 -4.0
    Rat (Acute) 2.74
    Rat (Chronic Oral) 1.9
    Fathead Minnow 3.83
    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 423.91
    Hydration Free Energy -6.95
    Log(D) at pH=7.4 2.85
    Log(P) 3.09
    Log S -3.56
    Log(Vapor Pressure) -9.23
    Melting Point 203.92
    pKa Acid 7.32
    pKa Basic 5.68