Jerantinine A acetate






Names

    • NSC783516
    • methyl (1R,12R,19S)-4-acetyloxy-12-ethyl-5-methoxy-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2,4,6,9,13-pentaene-10-carboxylate
    • Jerantinine A acetate
    • Jerantinine A Acetate
    • NSC-783516
    • CHEMBL499064
    • methyl (1R,12R,19S)-4-acetyloxy-12-ethyl-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9,13-pentaene-10-carboxylate

Attributes

  • Canonical SMILES

    CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)C5=CC(=C(C=C5N3)OC)OC(=O)C)C(=O)OC

  • InChI

    InChI=1S/C24H28N2O5/c1-5-23-7-6-9-26-10-8-24(22(23)26)16-11-19(31-14(2)27)18(29-3)12-17(16)25-20(24)15(13-23)21(28)30-4/h6-7,11-12,22,25H,5,8-10,13H2,1-4H3/t22-,23-,24-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 77.10000000000001
  • #RotBonds: 4
  • MW: 424.4970000000002
  • HBD: 1
  • HBA: 7
  • logP: 3.155100000000002
  • Chemical Formula: C24H28N2O5


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) -4.86
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.9
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -3.05
    Distribution Blood-Brain Barrier (Central Nervous System) -2.83
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.79
    Plasma Protein Binding 59.36
    Steady State Volume of Distribution 3.08
    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 Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.28
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.02
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.73
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.28
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -85.59
    Rat (Acute) 3.07
    Rat (Chronic Oral) 2.2
    Fathead Minnow 4.14
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 451.2
    Hydration Free Energy -2.81
    Log(D) at pH=7.4 2.99
    Log(P) 2.99
    Log S -3.61
    Log(Vapor Pressure) -8.03
    Melting Point 189.89
    pKa Acid 7.82
    pKa Basic 7.19