Taipinisine






Names

    • Taipinisine

Attributes

  • Canonical SMILES

    O=C(NC1=C2C=CC=C1)[C@]32[C@@]4([H])C[C@@]([H])(/C(CN4CC3)=C\C)C[C@@]5([H])C6=C(CCN5)C(C=CC=C7)=C7N6

  • InChI

    InChI=1S/C29H32N4O/c1-2-18-17-33-14-12-29(22-8-4-6-10-24(22)32-28(29)34)26(33)16-19(18)15-25-27-21(11-13-30-25)20-7-3-5-9-23(20)31-27/h2-10,19,25-26,30-31H,11-17H2,1H3,(H,32,34)/b18-2-/t19-,25-,26+,29+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 60.160000000000004
  • #RotBonds: 2
  • MW: 452.60200000000015
  • HBD: 3
  • HBA: 3
  • logP: 4.675400000000003
  • Chemical Formula: C29H32N4O


Species

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

External Databases


References

  • Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine. J Nat Prod, 2014 (PMID 25333996).

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) -5.33
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.29
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.38
    Distribution Blood-Brain Barrier (Central Nervous System) -2.57
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.14
    Plasma Protein Binding 91.35
    Steady State Volume of Distribution 5.19
    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 Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.35
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor -0.25
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.54
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.83
    Micronucleos Toxic
    NR-AhR Toxic
    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 -992.98
    Rat (Acute) 2.93
    Rat (Chronic Oral) 2.07
    Fathead Minnow 6.4
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Safe
    General Properties Boiling Point 500.74
    Hydration Free Energy -2.9
    Log(D) at pH=7.4 3.61
    Log(P) 3.16
    Log S -4.12
    Log(Vapor Pressure) -9.24
    Melting Point 225.74
    pKa Acid 10.49
    pKa Basic 7.44