Tacraline






Names

    • Tacraline

Attributes

  • Canonical SMILES

    C/C=C1[C@@]2([H])C[C@@H]3C4(N5)NC6=CC=CC=C6[C@@]4([C@@]2(C(OC)=O)COC(C)=O)CC5N3C/1

  • InChI

    InChI=1S/C23H27N3O4/c1-4-14-11-26-18-9-16(14)21(20(28)29-3,12-30-13(2)27)22-10-19(26)25-23(18,22)24-17-8-6-5-7-15(17)22/h4-8,16,18-19,24-25H,9-12H2,1-3H3/b14-4+/t16-,18-,19?,21+,22-,23?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 79.89999999999999
  • #RotBonds: 3
  • MW: 409.4860000000003
  • HBD: 2
  • HBA: 7
  • logP: 1.7520999999999998
  • Chemical Formula: C23H27N3O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. chippii Ivory Coast - Lg12291

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimicrobial

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) -5.14
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.04
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.21
    Distribution Blood-Brain Barrier (Central Nervous System) -2.64
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.97
    Plasma Protein Binding 49.24
    Steady State Volume of Distribution 3.56
    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 Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.74
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.78
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.65
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.13
    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 -76.2
    Rat (Acute) 3.57
    Rat (Chronic Oral) 2.06
    Fathead Minnow 4.1
    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 424.05
    Hydration Free Energy -3.88
    Log(D) at pH=7.4 1.78
    Log(P) 0.69
    Log S -3.16
    Log(Vapor Pressure) -9.11
    Melting Point 207.3
    pKa Acid 8.45
    pKa Basic 4.81