16-Epidregamine






Names

    • 16-Epidregamine

Attributes

  • Canonical SMILES

    CC[C@H]1CN(C)[C@H]2CC3=C(NC4=CC=CC=C34)C(CC1[C@H]2C(OC)=O)=O

  • 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+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.4
  • #RotBonds: 2
  • MW: 354.4500000000001
  • HBD: 1
  • HBA: 4
  • logP: 3.0424000000000015
  • Chemical Formula: C21H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    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).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticancer
    • 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) -4.82
    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 -1.63
    Distribution Blood-Brain Barrier (Central Nervous System) -2.3
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.94
    Plasma Protein Binding 57.51
    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 17.02
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.7
    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 -4.93
    Rat (Acute) 2.76
    Rat (Chronic Oral) 1.91
    Fathead Minnow 3.77
    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 425.11
    Hydration Free Energy -6.99
    Log(D) at pH=7.4 2.92
    Log(P) 3.03
    Log S -3.57
    Log(Vapor Pressure) -9.21
    Melting Point 197.11
    pKa Acid 7.39
    pKa Basic 5.66