3-Ketopropyl coronaridine






Names

    • 3-Ketopropyl coronaridine

Attributes

  • Canonical SMILES

    CC[C@H]1C2CC[C@]3(C(OC)=O)[C@@]1([H])N(CCC4=C3NC5=CC=CC=C45)C2C(CC)=O

  • InChI

    InChI=1S/C24H30N2O3/c1-4-14-16-10-12-24(23(28)29-3)21-17(15-8-6-7-9-18(15)25-21)11-13-26(22(14)24)20(16)19(27)5-2/h6-9,14,16,20,22,25H,4-5,10-13H2,1-3H3/t14-,16?,20?,22-,24+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.4
  • #RotBonds: 4
  • MW: 394.51500000000016
  • HBD: 1
  • HBA: 4
  • logP: 3.6029000000000018
  • Chemical Formula: C24H30N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. dichotoma Sri Lanka, Malaysia - -
    T. ventricosa Kenya 761103 AM2017/04

External Databases


References

  • Antileishmanial and cytotoxic activity of secondary metabolites from Taberneamontana ventricosa and two aloe species. Nat Prod Res, 2022 (PMID 33459049).
  • Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Med, 1984 (PMID 6484030).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antileishmanial
    • Spasmolytic
    • Cytotoxicity
    • Convulsive

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) -4.51
    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 Substrate
    Skin Permeability -1.24
    Distribution Blood-Brain Barrier (Central Nervous System) -2.97
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.21
    Plasma Protein Binding 60.0
    Steady State Volume of Distribution 4.11
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor 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 Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.78
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.82
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.89
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.31
    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 -39.04
    Rat (Acute) 3.04
    Rat (Chronic Oral) 1.93
    Fathead Minnow 4.16
    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 422.44
    Hydration Free Energy -4.2
    Log(D) at pH=7.4 3.61
    Log(P) 3.62
    Log S -3.97
    Log(Vapor Pressure) -8.65
    Melting Point 171.43
    pKa Acid 10.29
    pKa Basic 6.3