16-Epi-affinine






Names

    • 16-Epi-affinine

Attributes

  • Canonical SMILES

    C/C=C/1\CN([C@H]2CC3=C(C(=O)C[C@@H]1[C@H]2CO)NC4=CC=CC=C34)C

  • InChI

    InChI=1S/C20H24N2O2/c1-3-12-10-22(2)18-8-15-13-6-4-5-7-17(13)21-20(15)19(24)9-14(12)16(18)11-23/h3-7,14,16,18,21,23H,8-11H2,1-2H3/b12-3+/t14-,16+,18-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 56.330000000000005
  • #RotBonds: 1
  • MW: 324.42400000000004
  • HBD: 2
  • HBA: 3
  • logP: 2.7818000000000014
  • Chemical Formula: C20H24N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862
    T. chippii Ivory Coast - Lg12291

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Bio-guided search of active indole alkaloids from Tabernaemontana catharinensis: Antitumour activity, toxicity in silico and molecular modelling studies. Bioorg Chem, 2019 (PMID 30599414).
  • Chemical constituents antioxidant and anticholinesterasic activity of Tabernaemontana catharinensis. ScientificWorldJournal, 2013 (PMID 23983637).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticholinesterasic
    • Antitumor
    • Antimicrobial
    • Antioxidant
    • Cytotoxicity
    • Scavenging

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) -4.8
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.96
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.53
    Distribution Blood-Brain Barrier (Central Nervous System) -2.44
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.71
    Plasma Protein Binding 65.3
    Steady State Volume of Distribution 4.1
    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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 16.8
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.32
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.99
    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 -2.12
    Rat (Acute) 2.85
    Rat (Chronic Oral) 2.09
    Fathead Minnow 3.92
    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 426.31
    Hydration Free Energy -8.53
    Log(D) at pH=7.4 2.04
    Log(P) 2.44
    Log S -3.31
    Log(Vapor Pressure) -10.33
    Melting Point 185.02
    pKa Acid 8.04
    pKa Basic 6.3