10-O-Methyljerantinine A






Names

    • methyl (1R,12R,19S)-12-ethyl-4,5-dimethoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9,13-pentaene-10-carboxylate
    • methyl (1R,12R,19S)-12-ethyl-4,5-dimethoxy-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2,4,6,9,13-pentaene-10-carboxylate
    • 10-O-Methyljerantinine A
    • CHEMBL499341

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C23H28N2O4/c1-5-22-7-6-9-25-10-8-23(21(22)25)15-11-17(27-2)18(28-3)12-16(15)24-19(23)14(13-22)20(26)29-4/h6-7,11-12,21,24H,5,8-10,13H2,1-4H3/t21-,22-,23-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 60.03
  • #RotBonds: 4
  • MW: 396.48700000000014
  • HBD: 1
  • HBA: 6
  • logP: 3.2384000000000013
  • Chemical Formula: C23H28N2O4


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) -4.89
    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 -2.96
    Distribution Blood-Brain Barrier (Central Nervous System) -2.79
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.8
    Plasma Protein Binding 52.34
    Steady State Volume of Distribution 3.0
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 6.79
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.16
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.01
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.19
    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 Toxic
    T. Pyriformis -38.23
    Rat (Acute) 3.36
    Rat (Chronic Oral) 2.07
    Fathead Minnow 4.11
    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 444.77
    Hydration Free Energy -4.01
    Log(D) at pH=7.4 3.23
    Log(P) 2.91
    Log S -3.21
    Log(Vapor Pressure) -7.57
    Melting Point 186.86
    pKa Acid 8.3
    pKa Basic 7.62