Tacamine-N-oxide






Names

    • Tacamine-N-oxide

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C21H26N2O4/c1-3-13-10-14-11-21(25,20(24)27-2)22-17-7-5-4-6-15(17)16-8-9-23(26,12-13)19(14)18(16)22/h4-7,13-14,19,25H,3,8-12H2,1-2H3/t13-,14-,19-,21-,23?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 74.52000000000001
  • #RotBonds: 2
  • MW: 370.44900000000007
  • HBD: 1
  • HBA: 5
  • logP: 2.8210000000000015
  • Chemical Formula: C21H26N2O4


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) -5.62
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.83
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.52
    Distribution Blood-Brain Barrier (Central Nervous System) -3.6
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.52
    Plasma Protein Binding 68.34
    Steady State Volume of Distribution 1.21
    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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.69
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.66
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.4
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.1
    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 -10.5
    Rat (Acute) 2.59
    Rat (Chronic Oral) 2.03
    Fathead Minnow 4.03
    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 436.75
    Hydration Free Energy -5.83
    Log(D) at pH=7.4 2.06
    Log(P) 1.29
    Log S -1.51
    Log(Vapor Pressure) -8.7
    Melting Point 199.6
    pKa Acid 4.89
    pKa Basic 2.71