Tronoharine






Names

    • Tronoharine

Attributes

  • Canonical SMILES

    O=C1N2C3=CC=CC=C3[C@]45C2=C([C@]6([H])[C@H](CC)[C@@]4([H])N(CC6)CC5)C[C@H]1O

  • InChI

    InChI=1S/C21H24N2O2/c1-2-12-13-7-9-22-10-8-21(18(12)22)15-5-3-4-6-16(15)23-19(21)14(13)11-17(24)20(23)25/h3-6,12-13,17-18,24H,2,7-11H2,1H3/t12-,13-,17+,18+,21-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 43.78
  • #RotBonds: 1
  • MW: 336.4350000000001
  • HBD: 1
  • HBA: 3
  • logP: 2.4237000000000006
  • Chemical Formula: C21H24N2O2


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) -4.68
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.68
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.42
    Distribution Blood-Brain Barrier (Central Nervous System) -2.45
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.75
    Plasma Protein Binding 51.36
    Steady State Volume of Distribution 2.76
    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 Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.18
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.41
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.45
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.45
    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 -7.62
    Rat (Acute) 3.61
    Rat (Chronic Oral) 1.97
    Fathead Minnow 3.94
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 451.36
    Hydration Free Energy -4.9
    Log(D) at pH=7.4 1.92
    Log(P) 1.52
    Log S -2.87
    Log(Vapor Pressure) -8.54
    Melting Point 233.84
    pKa Acid 9.67
    pKa Basic 6.62