3-Oxoheyneanine






Names

    • 3-Oxoheyneanine

Attributes

  • Canonical SMILES

    C[C@H](O)[C@H]4C[C@H]3CC[C@](C45)(C(OC)=O)C2=C(CCN5[C@]3=O)C1=CC=CC=C1N2

  • InChI

    InChI=1S/C22H26N2O4/c1-12(25)16-11-13-7-9-22(21(27)28-2)18-15(8-10-24(19(16)22)20(13)26)14-5-3-4-6-17(14)23-18/h3-6,12-13,16,19,23,25H,7-11H2,1-2H3/t12-,13+,16+,19?,22-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 82.63
  • #RotBonds: 2
  • MW: 382.46000000000004
  • HBD: 2
  • HBA: 4
  • logP: 2.1426999999999996
  • Chemical Formula: C22H26N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. penduliflora Cameroon, 37036/HNC, Nigeria 761088 40,411 HCN

External Databases


References

  • Antiplasmodial activities of indole alkaloids from Tabernaemontana penduliflora K. Schum (Apocynaceae). Fitoterapia, 2021 (PMID 34029654).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Inhibitory

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) -4.93
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.91
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.68
    Distribution Blood-Brain Barrier (Central Nervous System) -2.81
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.66
    Plasma Protein Binding 52.72
    Steady State Volume of Distribution 5.65
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor 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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.33
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.63
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.42
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.13
    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 -16.58
    Rat (Acute) 3.59
    Rat (Chronic Oral) 2.25
    Fathead Minnow 3.98
    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 466.62
    Hydration Free Energy -6.99
    Log(D) at pH=7.4 2.13
    Log(P) 1.48
    Log S -3.3
    Log(Vapor Pressure) -9.45
    Melting Point 230.59
    pKa Acid 9.76
    pKa Basic 7.14