Voastrictine






Names

    • NSC 306219
    • Ibogamine-18-carboxylic acid, 20-hydroxy-12-methoxy-, methyl ester, (20S)-
    • methyl (1S,15R,17S,18S)-17-[(1S)-1-hydroxyethyl]-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
    • Voastrictine
    • Voacristine
    • 545-84-6
    • (?)-Voacangarine
    • Voacangarine

Attributes

  • Canonical SMILES

    C/C=C/1\CN2CC[C@]3([C@@H]2C[C@H]1C4=C3C5=CC=CC=C5N=C4)O

  • InChI

    InChI=1S/C19H20N2O/c1-2-12-11-21-8-7-19(22)17(21)9-14(12)15-10-20-16-6-4-3-5-13(16)18(15)19/h2-6,10,14,17,22H,7-9,11H2,1H3/b12-2+/t14-,17+,19-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 36.36
  • #RotBonds: 0
  • MW: 292.382
  • HBD: 1
  • HBA: 3
  • logP: 2.9439000000000015
  • Chemical Formula: C19H20N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    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).

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) -4.74
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.5
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.34
    Distribution Blood-Brain Barrier (Central Nervous System) -2.41
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.65
    Plasma Protein Binding 67.13
    Steady State Volume of Distribution 4.75
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.17
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.41
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.12
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.02
    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 -0.76
    Rat (Acute) 3.43
    Rat (Chronic Oral) 2.15
    Fathead Minnow 4.14
    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 395.03
    Hydration Free Energy -7.35
    Log(D) at pH=7.4 1.91
    Log(P) 2.45
    Log S -2.98
    Log(Vapor Pressure) -7.9
    Melting Point 188.25
    pKa Acid 9.58
    pKa Basic 7.03