Pleiocarpine






Names

    • Pleiocarpine

Attributes

  • Canonical SMILES

    COC(=O)[C@@H]1C[C@]23CCCN4[C@@H]2[C@@]5([C@]1(CC3)N(C6=CC=CC=C65)C(=O)OC)CC4

  • InChI

    InChI=1S/C23H28N2O4/c1-28-18(26)16-14-21-8-5-12-24-13-11-22(19(21)24)15-6-3-4-7-17(15)25(20(27)29-2)23(16,22)10-9-21/h3-4,6-7,16,19H,5,8-14H2,1-2H3/t16-,19-,21+,22+,23+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 59.08
  • #RotBonds: 1
  • MW: 396.4870000000002
  • HBD: 0
  • HBA: 5
  • logP: 3.0908000000000015
  • Chemical Formula: C23H28N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. contorta Cameroon 761060 N43440/HNC

External Databases


References

  • Indoline alkaloids from Tabernaemontana contorta with cancer chemopreventive activity. Phytochemistry, 2017 (PMID 28950224).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Inhibitory
    • Cancer chemopreventive

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) -4.48
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.65
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.59
    Distribution Blood-Brain Barrier (Central Nervous System) -2.27
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.89
    Plasma Protein Binding 58.23
    Steady State Volume of Distribution 2.22
    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 Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.31
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.66
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.63
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.29
    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 -52.41
    Rat (Acute) 3.87
    Rat (Chronic Oral) 2.22
    Fathead Minnow 3.97
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 466.12
    Hydration Free Energy -2.86
    Log(D) at pH=7.4 2.84
    Log(P) 2.63
    Log S -3.6
    Log(Vapor Pressure) -7.79
    Melting Point 232.24
    pKa Acid 9.09
    pKa Basic 6.59