Tacamonine






Names

    • (13R,15R,19R)-13-ethyl-1,11-diazapentacyclo(9.6.2.02,7.08,18.015,19)nonadeca-2,4,6,8(18)-tetraen-17-one
    • (13R,15R,19R)-13-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-one
    • Tacamonine
    • 90761-95-8
    • SCHEMBL1944441

Attributes

  • Canonical SMILES

    CC[C@@H]1C[C@@H]2CC(=O)N3C4=CC=CC=C4C5=C3[C@@H]2N(C1)CC5

  • InChI

    InChI=1S/C19H22N2O/c1-2-12-9-13-10-17(22)21-16-6-4-3-5-14(16)15-7-8-20(11-12)18(13)19(15)21/h3-6,12-13,18H,2,7-11H2,1H3/t12-,13-,18-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 25.240000000000002
  • #RotBonds: 1
  • MW: 294.39800000000014
  • HBD: 0
  • HBA: 3
  • logP: 3.6305000000000023
  • Chemical Formula: C19H22N2O


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) -4.6
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.51
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.1
    Distribution Blood-Brain Barrier (Central Nervous System) -2.76
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.69
    Plasma Protein Binding 60.52
    Steady State Volume of Distribution 2.05
    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 Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 4.16
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.28
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.04
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.88
    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 -0.98
    Rat (Acute) 3.17
    Rat (Chronic Oral) 1.36
    Fathead Minnow 4.04
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 405.4
    Hydration Free Energy -6.45
    Log(D) at pH=7.4 2.1
    Log(P) 3.47
    Log S -2.68
    Log(Vapor Pressure) -7.26
    Melting Point 178.13
    pKa Acid 10.13
    pKa Basic 6.16