19-Oxocoronaridine






Names

    • 19-Oxocoronaridine

Attributes

  • Canonical SMILES

    CC([C@@H]1C[C@H]2C[C@@]3(C(OC)=O)C1[N@](CCC4=C3NC5=CC=CC=C45)C2)=O

  • InChI

    InChI=1S/C21H24N2O3/c1-12(24)16-9-13-10-21(20(25)26-2)18-15(7-8-23(11-13)19(16)21)14-5-3-4-6-17(14)22-18/h3-6,13,16,19,22H,7-11H2,1-2H3/t13-,16-,19?,21-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.4
  • #RotBonds: 2
  • MW: 352.4340000000001
  • HBD: 1
  • HBA: 4
  • logP: 2.4342000000000006
  • Chemical Formula: C21H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. heyneana India 2563820 -
    T. holstii Kenya - -

External Databases


References

  • Alkaloid studies. 8. Isolation and characterization of alkaloids of Tabernaemontana heyneana Wall and antifertility properties of coronaridine. J Pharm Sci, 1973 (PMID 4714135).
  • Plant anticancer agents III: Isolation of indole and bisindole alkaloids from Tabernaemontana holstii roots. J Pharm Sci, 1977 (PMID 561182).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Reproducible
    • Inhibitory
    • Antifertility
    • Cytotoxicity
    • Estrogenic

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) -4.56
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.73
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.4
    Distribution Blood-Brain Barrier (Central Nervous System) -2.83
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.83
    Plasma Protein Binding 55.19
    Steady State Volume of Distribution 4.69
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.82
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.21
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.74
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.64
    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 -8.46
    Rat (Acute) 3.13
    Rat (Chronic Oral) 1.98
    Fathead Minnow 3.99
    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 410.14
    Hydration Free Energy -4.47
    Log(D) at pH=7.4 2.14
    Log(P) 1.5
    Log S -3.3
    Log(Vapor Pressure) -8.3
    Melting Point 227.89
    pKa Acid 8.86
    pKa Basic 7.76