3-Oxovoacangine






Names

    • BDBM50044110
    • CHEMBL3325765
    • 3-Oxovoacangine

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2=O)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC

  • InChI

    InChI=1S/C22H26N2O4/c1-4-12-9-13-11-22(21(26)28-3)18-15(7-8-24(19(12)22)20(13)25)16-10-14(27-2)5-6-17(16)23-18/h5-6,10,12-13,19,23H,4,7-9,11H2,1-3H3/t12-,13+,19-,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.63
  • #RotBonds: 3
  • MW: 382.46000000000015
  • HBD: 1
  • HBA: 4
  • logP: 2.790400000000001
  • Chemical Formula: C22H26N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. cymosa Colombia 761066 JBC3243
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • The Antiviral and Virucidal Activities of Voacangine and Structural Analogs Extracted from Tabernaemontana cymosa Depend on the Dengue Virus Strain. Plants (Basel), 2021 (PMID 34201900).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity
    • Antiviral

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 -4.87
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.85
    Distribution Blood-Brain Barrier (Central Nervous System) -2.86
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.9
    Plasma Protein Binding 59.18
    Steady State Volume of Distribution 5.0
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.16
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.25
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.47
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.79
    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 -21.05
    Rat (Acute) 2.99
    Rat (Chronic Oral) 2.31
    Fathead Minnow 4.01
    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 475.89
    Hydration Free Energy -6.31
    Log(D) at pH=7.4 2.82
    Log(P) 2.62
    Log S -4.06
    Log(Vapor Pressure) -8.57
    Melting Point 232.07
    pKa Acid 10.26
    pKa Basic 6.99