Nb-Methylaffinisine






Names

    • Nb-Methylaffinisine

Attributes

  • Canonical SMILES

    C/C=C1C[N+]2(C)[C@H]3C[C@H]/1[C@H](CO)[C@@H]2CC4=C3N(C)C5=CC=CC=C45

  • InChI

    InChI=1S/C21H27N2O/c1-4-13-11-23(3)19-10-16-14-7-5-6-8-18(14)22(2)21(16)20(23)9-15(13)17(19)12-24/h4-8,15,17,19-20,24H,9-12H2,1-3H3/q+1/b13-4-/t15-,17+,19+,20+,23?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 25.16
  • #RotBonds: 1
  • MW: 323.46000000000004
  • HBD: 1
  • HBA: 2
  • logP: 3.179000000000002
  • Chemical Formula: C21H27N2O+


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. contorta Cameroon 761060 N43440/HNC
    T. laeta Brazil 761076 WAG

External Databases


References

  • Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Nat Prod Res, 2021 (PMID 31274013).
  • Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc, 2008 (PMID 18797794).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticolon cancer
    • Acetylbutyrylcholinesterase inhibitory

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) -4.93
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.74
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.76
    Distribution Blood-Brain Barrier (Central Nervous System) -3.2
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.71
    Plasma Protein Binding 61.08
    Steady State Volume of Distribution 1.41
    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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.74
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 1.01
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.03
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.75
    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 -0.47
    Rat (Acute) 3.36
    Rat (Chronic Oral) 1.64
    Fathead Minnow 4.31
    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 453.62
    Hydration Free Energy -4.58
    Log(D) at pH=7.4 1.46
    Log(P) 0.14
    Log S -1.32
    Log(Vapor Pressure) -9.85
    Melting Point 256.44
    pKa Acid 8.5
    pKa Basic 5.22