Vobasidine D






Names

    • Vobasidine D

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C21H22N2O4/c1-11(24)15-10-23(2)17-8-14-12-6-4-5-7-16(12)22-20(14)18(25)9-13(15)19(17)21(26)27-3/h4-7,10,13,17,19,22H,8-9H2,1-3H3/t13-,17+,19?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 79.47
  • #RotBonds: 2
  • MW: 366.41700000000014
  • HBD: 1
  • HBA: 5
  • logP: 2.4891000000000005
  • Chemical Formula: C21H22N2O4


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) -4.78
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.71
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.73
    Distribution Blood-Brain Barrier (Central Nervous System) -2.58
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.0
    Plasma Protein Binding 62.71
    Steady State Volume of Distribution 2.57
    Metabolism Breast Cancer Resistance Protein Non-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 12.96
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.76
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.24
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 3.15
    Micronucleos Toxic
    NR-AhR Toxic
    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 Toxic
    T. Pyriformis -7.29
    Rat (Acute) 2.83
    Rat (Chronic Oral) 2.3
    Fathead Minnow 4.19
    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 451.72
    Hydration Free Energy -7.53
    Log(D) at pH=7.4 2.3
    Log(P) 2.17
    Log S -4.21
    Log(Vapor Pressure) -9.46
    Melting Point 213.23
    pKa Acid 8.35
    pKa Basic 5.81