Vernavosine






Names

    • Vernavosine

Attributes

  • Canonical SMILES

    O=C1[C@@]2(O)N([C@@](C[C@@]([C@@H](C(OC)=O)[C@H](O)CC3)([H])[C@]3([H])C4)([H])N4CC2)C5=CC=CC=C15

  • InChI

    InChI=1S/C21H26N2O5/c1-28-20(26)18-14-10-17-22(11-12(14)6-7-16(18)24)9-8-21(27)19(25)13-4-2-3-5-15(13)23(17)21/h2-5,12,14,16-18,24,27H,6-11H2,1H3/t12-,14-,16+,17+,18+,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 90.31
  • #RotBonds: 1
  • MW: 386.44800000000015
  • HBD: 2
  • HBA: 7
  • logP: 0.9896999999999991
  • Chemical Formula: C21H26N2O5


Species

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

External Databases


References

  • A Hexacyclic, Iboga-Derived Monoterpenoid Indole with a Contracted Tetrahydroazepine C-Ring and Incorporation of an Isoxazolidine Moiety, a Seco-Corynanthean, an Aspidosperma-Aspidosperma Bisindole with Anticancer Properties, and the Absolute Configuration of the Pyridopyrimidine Indole Alkaloid, Vernavosine. J Nat Prod, 2016 (PMID 27759387).
  • Criofolinine and vernavosine, new pentacyclic indole alkaloids incorporating pyrroloazepine and pyridopyrimidine moieties derived from a common yohimbine precursor. Org Lett, 2014 (PMID 25454201).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity
    • 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) -4.99
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.88
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.44
    Distribution Blood-Brain Barrier (Central Nervous System) -2.9
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.45
    Plasma Protein Binding 47.53
    Steady State Volume of Distribution 2.31
    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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.07
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.89
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.15
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.79
    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 -20.23
    Rat (Acute) 3.61
    Rat (Chronic Oral) 2.21
    Fathead Minnow 4.03
    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 439.61
    Hydration Free Energy -6.15
    Log(D) at pH=7.4 1.32
    Log(P) 0.41
    Log S -2.44
    Log(Vapor Pressure) -9.07
    Melting Point 208.16
    pKa Acid 5.74
    pKa Basic 5.92