Tacamine






Names

    • Tacamine

Attributes

  • Canonical SMILES

    CC[C@](C1)([H])C[C@]2([H])C[C@](C(OC)=O)(O)N(C3=C4CCN1[C@]23[H])C5=C4C=CC=C5

  • InChI

    InChI=1S/C21H26N2O3/c1-3-13-10-14-11-21(25,20(24)26-2)23-17-7-5-4-6-15(17)16-8-9-22(12-13)18(14)19(16)23/h4-7,13-14,18,25H,3,8-12H2,1-2H3/t13-,14-,18-,21-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.7
  • #RotBonds: 2
  • MW: 354.45000000000005
  • HBD: 1
  • HBA: 5
  • logP: 2.8084000000000016
  • Chemical Formula: C21H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. eglandulosa Malaysia, China 761067 -

External Databases


References

  • Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine. J Nat Prod, 2014 (PMID 25333996).
  • Tacamine, the first example of a new class of indole alkaloids Tetrahedron Letters, 1982 (DOI).

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) -4.86
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.78
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.44
    Distribution Blood-Brain Barrier (Central Nervous System) -2.96
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.76
    Plasma Protein Binding 50.68
    Steady State Volume of Distribution 3.96
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate 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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.79
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.75
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.62
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 9.09
    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 -11.43
    Rat (Acute) 3.07
    Rat (Chronic Oral) 1.68
    Fathead Minnow 4.1
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 403.01
    Hydration Free Energy -6.53
    Log(D) at pH=7.4 2.71
    Log(P) 2.91
    Log S -2.52
    Log(Vapor Pressure) -8.37
    Melting Point 174.3
    pKa Acid 8.25
    pKa Basic 7.44