Isovoacangina






Names

    • NSC 195198
    • DTXSID601316325
    • Ibogamine-18-carboxylic acid, 13-methoxy-, methyl ester
    • Isovoacangina
    • (-)-Isovoacangine
    • 596-54-3

Attributes

  • Canonical SMILES

    O=C(OC)[C@]([C@H]1[N@@](C2)CC3)(C[C@@]2([H])C[C@@H]1CC)C4=C3C(C=CC(OC)=C5)=C5N4

  • InChI

    InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-17(7-8-24(12-13)20(14)22)16-6-5-15(26-2)10-18(16)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14+,20+,22-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.559999999999995
  • #RotBonds: 3
  • MW: 368.47700000000003
  • HBD: 1
  • HBA: 4
  • logP: 3.2638000000000016
  • Chemical Formula: C22H28N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. crassa Ghana 761062 20161116

External Databases


References

  • New Monoterpenoid Indole Alkaloids from Tabernaemontana crassa Inhibit β-Amyloid42 Production and Phospho-Tau (Thr217). Int J Mol Sci, 2023 (PMID 36675001).

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) -4.68
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.98
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.56
    Distribution Blood-Brain Barrier (Central Nervous System) -2.69
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.76
    Plasma Protein Binding 63.09
    Steady State Volume of Distribution 5.15
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.14
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.31
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.17
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.63
    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 Safe
    T. Pyriformis -13.93
    Rat (Acute) 2.87
    Rat (Chronic Oral) 2.03
    Fathead Minnow 3.97
    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 457.36
    Hydration Free Energy -5.32
    Log(D) at pH=7.4 3.14
    Log(P) 3.03
    Log S -3.78
    Log(Vapor Pressure) -8.3
    Melting Point 230.52
    pKa Acid 10.0
    pKa Basic 7.48