Coronaridine 3,4-iminium






Names

    • Coronaridine 3,4-iminium

Attributes

  • Canonical SMILES

    O=C(OC)[C@@]1([C@H]2[N+](CC3)=C[C@@H](C[C@H]2CC)C1)C4=C3C(C=CC=C5)=C5N4

  • InChI

    InChI=1S/C21H25N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,12-14,19,22H,3,8-11H2,1-2H3/q+1/t13-,14+,19-,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 45.1
  • #RotBonds: 2
  • MW: 337.443
  • HBD: 1
  • HBA: 2
  • logP: 3.036500000000001
  • Chemical Formula: C21H25N2O2+


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. peduncularis Thailand 761087 WU 0099055

External Databases


References

  • Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata. Molecules, 2023 (PMID 37764440).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiproliferative
    • 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) -4.87
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.79
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.48
    Distribution Blood-Brain Barrier (Central Nervous System) -2.26
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.12
    Plasma Protein Binding 61.49
    Steady State Volume of Distribution 4.93
    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 Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.01
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.13
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.71
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.95
    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) 2.53
    Rat (Chronic Oral) 1.55
    Fathead Minnow 3.92
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 435.11
    Hydration Free Energy -5.84
    Log(D) at pH=7.4 3.41
    Log(P) 1.52
    Log S -2.53
    Log(Vapor Pressure) -8.55
    Melting Point 200.62
    pKa Acid 10.95
    pKa Basic 6.11