10-O-Methyljerantinine B






Names

    • methyl (1R,12S,13R,15S,20R)-12-ethyl-4,5-dimethoxy-14-oxa-8,17-diazahexacyclo(10.7.1.01,9.02,7.013,15.017,20)icosa-2,4,6,9-tetraene-10-carboxylate
    • 10-O-Methyljerantinine B
    • CHEMBL525066
    • methyl (1R,12S,13R,15S,20R)-12-ethyl-4,5-dimethoxy-14-oxa-8,17-diazahexacyclo[10.7.1.01,9.02,7.013,15.017,20]icosa-2,4,6,9-tetraene-10-carboxylate

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C23H28N2O5/c1-5-22-10-12(20(26)29-4)18-23(6-7-25(21(22)23)11-17-19(22)30-17)13-8-15(27-2)16(28-3)9-14(13)24-18/h8-9,17,19,21,24H,5-7,10-11H2,1-4H3/t17-,19-,21-,22+,23-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 72.56
  • #RotBonds: 4
  • MW: 412.48600000000016
  • HBD: 1
  • HBA: 7
  • logP: 2.4496
  • Chemical Formula: C23H28N2O5


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) -5.3
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.0
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.74
    Distribution Blood-Brain Barrier (Central Nervous System) -3.0
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.53
    Plasma Protein Binding 26.03
    Steady State Volume of Distribution 2.47
    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 Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 12.86
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.45
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.91
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 9.07
    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 -82.06
    Rat (Acute) 2.74
    Rat (Chronic Oral) 2.0
    Fathead Minnow 4.1
    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 458.46
    Hydration Free Energy -2.98
    Log(D) at pH=7.4 2.74
    Log(P) 1.75
    Log S -2.8
    Log(Vapor Pressure) -8.33
    Melting Point 178.93
    pKa Acid 5.66
    pKa Basic 6.89