Vobasenal






Names

    • Vobasenal

Attributes

  • Canonical SMILES

    O=C1C2=C(C3=CC=CC=C3N2)C[C@]([C@@]4([H])C(OC)=O)([H])N(C)C[C@@H](C=O)[C@@]4([H])C1

  • InChI

    InChI=1S/C20H22N2O4/c1-22-9-11(10-23)13-8-17(24)19-14(7-16(22)18(13)20(25)26-2)12-5-3-4-6-15(12)21-19/h3-6,10-11,13,16,18,21H,7-9H2,1-2H3/t11-,13+,16-,18-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 79.47
  • #RotBonds: 2
  • MW: 354.4060000000001
  • HBD: 1
  • HBA: 5
  • logP: 1.8313000000000001
  • Chemical Formula: C20H22N2O4


Species

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

External Databases


References

  • Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine. J Nat Prod, 2014 (PMID 25333996).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity

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 -4.78
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.08
    Distribution Blood-Brain Barrier (Central Nervous System) -2.49
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.55
    Plasma Protein Binding 41.38
    Steady State Volume of Distribution 2.2
    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 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 14.45
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.81
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.57
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.36
    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 -5.68
    Rat (Acute) 2.61
    Rat (Chronic Oral) 1.47
    Fathead Minnow 4.11
    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 430.3
    Hydration Free Energy -9.23
    Log(D) at pH=7.4 2.08
    Log(P) 1.71
    Log S -2.99
    Log(Vapor Pressure) -9.3
    Melting Point 201.13
    pKa Acid 6.41
    pKa Basic 6.44