Tacamonine-N-oxide






Names

    • Tacamonine-N-oxide

Attributes

  • Canonical SMILES

    CC[C@@]1([H])C[N+]([O-])(CCC2=C3N(C(C4)=O)C5=C2C=CC=C5)[C@]3([H])[C@]4([H])C1

  • InChI

    InChI=1S/C19H22N2O2/c1-2-12-9-13-10-17(22)20-16-6-4-3-5-14(16)15-7-8-21(23,11-12)19(13)18(15)20/h3-6,12-13,19H,2,7-11H2,1H3/t12-,13-,19-,21?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 45.06
  • #RotBonds: 1
  • MW: 310.39700000000005
  • HBD: 0
  • HBA: 3
  • logP: 3.6431000000000022
  • Chemical Formula: C19H22N2O2


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) -5.3
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.65
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.12
    Distribution Blood-Brain Barrier (Central Nervous System) -3.4
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.67
    Plasma Protein Binding 79.66
    Steady State Volume of Distribution 0.81
    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 Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.73
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.24
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.12
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.3
    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 1.52
    Rat (Acute) 2.59
    Rat (Chronic Oral) 1.83
    Fathead Minnow 4.0
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 427.12
    Hydration Free Energy -5.51
    Log(D) at pH=7.4 1.95
    Log(P) 1.71
    Log S -1.57
    Log(Vapor Pressure) -8.47
    Melting Point 201.19
    pKa Acid 6.37
    pKa Basic 1.94