Jerantiphylline B






Names

    • Jerantiphylline B

Attributes

  • Canonical SMILES

    COC(C=C1N2)=C(O)C=C1[C@@]34C2=C(C(OC)=O)C[C@@](C=CC5=O)(CC)[C@]3([H])N5CC4

  • InChI

    InChI=1S/C22H24N2O5/c1-4-21-6-5-17(26)24-8-7-22(20(21)24)13-9-15(25)16(28-2)10-14(13)23-18(22)12(11-21)19(27)29-3/h5-6,9-10,20,23,25H,4,7-8,11H2,1-3H3/t20-,21-,22-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 88.09999999999998
  • #RotBonds: 3
  • MW: 396.44300000000015
  • HBD: 2
  • HBA: 6
  • logP: 2.4620000000000006
  • Chemical Formula: C22H24N2O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. corymbose Malaysia - K667

External Databases


References

  • Jerantinines A-G, cytotoxic Aspidosperma alkaloids from Tabernaemontana corymbosa. J Nat Prod, 2008 (PMID 18778099).
  • Seco-tabersonine alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2009 (PMID 19217125).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -5.03
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.06
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.34
    Distribution Blood-Brain Barrier (Central Nervous System) -2.78
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.71
    Plasma Protein Binding 59.92
    Steady State Volume of Distribution 1.87
    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 Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.94
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.69
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.95
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.87
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Toxic
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -33.15
    Rat (Acute) 2.35
    Rat (Chronic Oral) 2.39
    Fathead Minnow 4.03
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Toxic
    General Properties Boiling Point 470.59
    Hydration Free Energy -4.47
    Log(D) at pH=7.4 2.41
    Log(P) 1.71
    Log S -3.41
    Log(Vapor Pressure) -8.33
    Melting Point 242.97
    pKa Acid 7.52
    pKa Basic 6.38