Vincamajicine






Names

    • Vincamajicine

Attributes

  • Canonical SMILES

    CN1[C@]2([C@]3(C[C@]4(C(OC)=O)[C@](C3)([N@@]5[C@]2(C[C@]4(/C(=C\C)/C5)[H])[H])[H])C=6C1=CC=CC6)[H]

  • InChI

    InChI=1S/C22H26N2O2/c1-4-13-11-24-17-9-15(13)22(20(25)26-3)12-21(10-18(22)24)14-7-5-6-8-16(14)23(2)19(17)21/h4-8,15,17-19H,9-12H2,1-3H3/b13-4-/t15-,17-,18-,19+,21+,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 32.78
  • #RotBonds: 1
  • MW: 350.4620000000001
  • HBD: 0
  • HBA: 4
  • logP: 2.728600000000001
  • Chemical Formula: C22H26N2O2


Species

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

External Databases


References

  • Ibogan, tacaman, and cytotoxic bisindole alkaloids from tabernaemontana. Cononusine, an iboga alkaloid with unusual incorporation of a pyrrolidone moiety. J Nat Prod, 2015 (PMID 25919190).

Compound-Protein Relationships


Compound Activities

    • Growth 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) -4.53
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.87
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.42
    Distribution Blood-Brain Barrier (Central Nervous System) -2.17
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.78
    Plasma Protein Binding 60.51
    Steady State Volume of Distribution 4.26
    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 5.95
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -0.14
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.27
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.87
    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 -8.78
    Rat (Acute) 4.77
    Rat (Chronic Oral) 1.38
    Fathead Minnow 4.0
    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 448.79
    Hydration Free Energy -2.25
    Log(D) at pH=7.4 2.39
    Log(P) 2.49
    Log S -3.57
    Log(Vapor Pressure) -8.38
    Melting Point 213.52
    pKa Acid 7.46
    pKa Basic 7.96