Isotabernamine






Names

    • 91794-13-7
    • Isotabernamine

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@@H]3[C@@H]1[N@](CCC4=C3NC5=C4C=C([C@@H]6C[C@@H]7[C@H](C(OC)=O)[C@@H](N(C)C/C7=C\C)CC8=C6NC9=CC=CC=C89)C=C5)C2

  • InChI

    InChI=1S/C40H48N4O2/c1-5-23-15-22-16-32-37-27(13-14-44(20-22)39(23)32)30-17-25(11-12-34(30)42-37)29-18-28-24(6-2)21-43(3)35(36(28)40(45)46-4)19-31-26-9-7-8-10-33(26)41-38(29)31/h6-12,17,22-23,28-29,32,35-36,39,41-42H,5,13-16,18-21H2,1-4H3/b24-6+/t22-,23-,28-,29-,32-,35-,36-,39+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 64.36
  • #RotBonds: 3
  • MW: 616.8500000000003
  • HBD: 2
  • HBA: 4
  • logP: 7.153100000000007
  • Chemical Formula: C40H48N4O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases

    • PubChem CID: 6442983
    • CAS RN: 91794-13-7

References

  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity
    • Antiinflammatory
    • Acetylcholinesterase inhibitory

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) -5.87
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -3.94
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 213.95
    Distribution Blood-Brain Barrier (Central Nervous System) -3.42
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.54
    Plasma Protein Binding 103.29
    Steady State Volume of Distribution 5.54
    Metabolism Breast Cancer Resistance Protein 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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.8
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.46
    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 6.55
    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 -386379.74
    Rat (Acute) 2.89
    Rat (Chronic Oral) 2.12
    Fathead Minnow 492.91
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 39799.06
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.27
    Log(P) 6.12
    Log S -5.89
    Log(Vapor Pressure) -1288.68
    Melting Point 295.31
    pKa Acid 6.87
    pKa Basic 6.7