Jerantinine E






Names

    • methyl (1R,12S,19S)-12-ethyl-4-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9-tetraene-10-carboxylate
    • DTXSID201317757
    • CHEMBL496470
    • methyl (1R,12S,19S)-12-ethyl-4-hydroxy-5-methoxy-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2,4,6,9-tetraene-10-carboxylate
    • Q27134644
    • CHEBI:66123
    • Jerantinine E
    • 1067224-94-5
    • Methyl (5alpha,12beta,19alpha)-15-hydroxy-16-methoxy-2,3-didehydroaspidospermidine-3-carboxylate

Attributes

  • Canonical SMILES

    CC[C@@]12CCCN3[C@@H]1[C@@]4(CC3)C5=CC(=C(C=C5NC4=C(C2)C(=O)OC)OC)O

  • InChI

    InChI=1S/C22H28N2O4/c1-4-21-6-5-8-24-9-7-22(20(21)24)14-10-16(25)17(27-2)11-15(14)23-18(22)13(12-21)19(26)28-3/h10-11,20,23,25H,4-9,12H2,1-3H3/t20-,21-,22-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.03000000000002
  • #RotBonds: 3
  • MW: 384.47600000000017
  • HBD: 2
  • HBA: 6
  • logP: 3.159400000000001
  • Chemical Formula: C22H28N2O4


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


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) -4.99
    Human Oral Bioavailability 20% 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 -2.63
    Distribution Blood-Brain Barrier (Central Nervous System) -2.79
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.58
    Plasma Protein Binding 51.81
    Steady State Volume of Distribution 3.84
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.28
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.89
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.28
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.95
    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 -20.88
    Rat (Acute) 2.52
    Rat (Chronic Oral) 2.3
    Fathead Minnow 4.02
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 440.1
    Hydration Free Energy -5.56
    Log(D) at pH=7.4 2.75
    Log(P) 2.59
    Log S -3.34
    Log(Vapor Pressure) -7.93
    Melting Point 224.87
    pKa Acid 7.47
    pKa Basic 7.52