Vobasidine A






Names

    • Vobasidine A

Attributes

  • Canonical SMILES

    O=C1C2=C(C3=CC=CC=C3N2)C[C@](C4C(OC)=O)([H])N(C)C[C@]5([C@H](O5)C)[C@@]4([H])C1

  • InChI

    InChI=1S/C21H24N2O4/c1-11-21(27-11)10-23(2)16-8-13-12-6-4-5-7-15(12)22-19(13)17(24)9-14(21)18(16)20(25)26-3/h4-7,11,14,16,18,22H,8-10H2,1-3H3/t11-,14+,16+,18?,21+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 74.93
  • #RotBonds: 1
  • MW: 368.43300000000016
  • HBD: 1
  • HBA: 5
  • logP: 2.1737
  • Chemical Formula: C21H24N2O4


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) -4.98
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.8
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.54
    Distribution Blood-Brain Barrier (Central Nervous System) -2.6
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.53
    Plasma Protein Binding 22.09
    Steady State Volume of Distribution 2.47
    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 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 16.78
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.84
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.06
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 9.23
    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 -12.91
    Rat (Acute) 2.87
    Rat (Chronic Oral) 1.64
    Fathead Minnow 4.07
    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 435.84
    Hydration Free Energy -7.03
    Log(D) at pH=7.4 1.71
    Log(P) 1.59
    Log S -2.58
    Log(Vapor Pressure) -8.73
    Melting Point 183.3
    pKa Acid 5.96
    pKa Basic 6.44