Jerantinine D






Names

    • Jerantinine D
    • CHEMBL525919
    • methyl (1R,12S,13R,15R,20R)-12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.01,9.02,7.013,15.017,20]icosa-2,4,6,9-tetraene-10-carboxylate
    • methyl (1R,12S,13R,15R,20R)-12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo(10.7.1.01,9.02,7.013,15.017,20)icosa-2,4,6,9-tetraene-10-carboxylate
    • CHEBI:66122
    • Q27134641
    • 1067224-93-4
    • methyl (5alpha,6alpha,7alpha,12beta,19alpha)-15-hydroxy-16-methoxy-8-oxo-2,3-didehydro-6,7-epoxyaspidospermidine-3-carboxylate
    • DTXSID301317617

Attributes

  • Canonical SMILES

    CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)C(=O)[C@H]5[C@@H]2O5)C6=CC(=C(C=C6N3)OC)O)C(=O)OC

  • InChI

    InChI=1S/C22H24N2O6/c1-4-21-9-10(19(27)29-3)16-22(11-7-13(25)14(28-2)8-12(11)23-16)5-6-24(20(21)22)18(26)15-17(21)30-15/h7-8,15,17,20,23,25H,4-6,9H2,1-3H3/t15-,17+,20+,21-,22+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 100.63000000000001
  • #RotBonds: 3
  • MW: 412.4420000000001
  • HBD: 2
  • HBA: 7
  • logP: 1.6731999999999996
  • Chemical Formula: C22H24N2O6


Species

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

External Databases


References

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

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) -5.42
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.16
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.01
    Distribution Blood-Brain Barrier (Central Nervous System) -3.07
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.56
    Plasma Protein Binding 34.11
    Steady State Volume of Distribution 1.97
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 16.26
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.55
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.2
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 4.06
    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 -71.77
    Rat (Acute) 2.49
    Rat (Chronic Oral) 2.44
    Fathead Minnow 4.06
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 495.54
    Hydration Free Energy -2.9
    Log(D) at pH=7.4 1.27
    Log(P) 1.03
    Log S -3.32
    Log(Vapor Pressure) -8.82
    Melting Point 238.73
    pKa Acid 5.65
    pKa Basic 5.45