Vobasidine B






Names

    • Vobasidine B

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C21H24N2O3/c1-4-12-11-23(2)17-9-15-13-7-5-6-8-16(13)22-20(15)18(24)10-14(12)19(17)21(25)26-3/h5-8,11,14,17,19,22H,4,9-10H2,1-3H3/t14-,17+,19?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.400000000000006
  • #RotBonds: 2
  • MW: 352.43400000000014
  • HBD: 1
  • HBA: 4
  • logP: 3.310100000000002
  • Chemical Formula: C21H24N2O3


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) -4.82
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.84
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.97
    Distribution Blood-Brain Barrier (Central Nervous System) -2.0
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.1
    Plasma Protein Binding 56.96
    Steady State Volume of Distribution 4.16
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate 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 14.75
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.46
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.56
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.68
    Micronucleos Toxic
    NR-AhR Toxic
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Toxic
    T. Pyriformis -4.81
    Rat (Acute) 2.72
    Rat (Chronic Oral) 1.99
    Fathead Minnow 4.2
    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 431.43
    Hydration Free Energy -6.81
    Log(D) at pH=7.4 3.09
    Log(P) 3.52
    Log S -4.11
    Log(Vapor Pressure) -9.36
    Melting Point 189.78
    pKa Acid 8.98
    pKa Basic 5.02